23 Best Family Road Trips from Chicago

Chicago's got it all - from its towering skyline and delicious deep-dish pizza to a cultural scene that's second to none. The city also boasts an amazing location and if you're on the hunt for your next family getaway, you're in luck. The Midwest is full of places that are just a drive away from Chicago.

On our list of 23 best family road trips from Chicago, you will find everything from amusement parks and peaceful nature retreats to fascinating historical sites and hands-on museums. There's something out there for families of all shapes and sizes.

That's exactly why we've put together a go-to list of the best family road trips from Chicago. So get your car games ready, and pack your books and keep reading to discover our top picks for family road trips, including how far you'll need to travel and what exciting attractions await at each destination.

Below, you will find our shortlist of amazing adventures on the road for all the family members, young in age or young at heart!

Best family road trips from Chicago: a quick overview

But that's not all; there are many other road trips you can enjoy from Chicago. If you are traveling during spring break, you can refer to our best spring break road trips from Chicago. Alternatively, for the colder months, you can check out our guide to the best winter road trips from Chicago.

Not sure when you want to travel and want to be inspired? You can find amazing ideas in our guide to the best road trips from Chicago.

Family-friendly day trips from Chicago (under 3 hours each way)

Day trips are perfect getaways, especially if you are traveling with younger children, and there are so many amazing places to visit with family near Chicago. From amusement parks to interesting museums, you will be spoilt for choice!

1. Gurnee

45 minutes from Chicago (40 miles)

Why visit Gurnee with family? The shortest drive on our list, which is perfect for a day trip, Gurnee is home to numerous theme parks, water parks and shopping centers.

Even though Gurnee is not exactly a city on its own but a suburb of the Chicago metropolitan area, there was no way we could not include this amazing location on our list of family road trips.

The town is also known for lovely beaches, hiking and biking. With these attractions, Gurnee is truly a premier family destination on Lake Michigan.

Driving to Gurnee from Chicago: The drive from Chicago city center to Gurnee is quite straightforward. Just follow Interstate 94 (I-94) north and then take US-41 to reach your destination.

Our highlights: Six Flags Great America is a wonderful theme park for travelers of any age. Here, you can enjoy a double-decker carousel, an atmospheric County Fair section or the themed Yukon Territory Section, or take a ride on the thrilling roller coasters.

Great Wolf Lodge's indoor water park is a fabulous family destination. It is a whole world of play, with various slides, pools, adventurous attractions, and a children's play area.

Once you have had your fill of thrills, Gurnee Mills is a large shopping center with over 200 stores and plenty of restaurants and cafés to enjoy.

If you are in the mood for a more serene afternoon with your family, you can pack a picnic and enjoy the waters and scenery of Lake Michigan at Illinois Beach State Park.

Did you know? On average, 23 million visitors find their way to Gurnee every year, showing the popularity of this Chicago suburb on Lake Michigan!

Things to note: Gurnee is close to Chicago and a popular destination, so traffic is often fairly busy on this stretch. Be vigilant on the road, especially if you're going to Gurnee in winter and snowy conditions.

Six Flags Great America is temporarily closed, but it is set to reopen this year. Please check before traveling to avoid any disappointment.

2. Harbor Country

Via Indiana Dunes National Park

1 hour 25 minutes from Chicago (75 miles)

Why visit Harbor County with family? Harbor Country, on the southwestern shore of Lake Michigan, is a great day trip destination for the entire family. It is just a short drive away from Chicago, and what draws people here are the lovely beaches, bed and breakfasts, and vineyards.

The area is also known for beautiful hiking, birding, swimming, and other lake-based activities. For families, there are also amazing farmers' markets, family-owned farms, and more to enjoy.

Driving to Harbor County from Chicago: Head south on I-90 out of Chicago and follow the shore until you reach Indiana Dunes National Park. From here, you will switch to I-94, heading east to reach Harbor County.

Our highlights: Indiana Dunes National Park is a top lakeside destination on the way to Harbor Country. On top of swimming and exploring the dunes, you can do bird watching and learn about the various vegetation types found in the area, from shorelines to wetlands, prairies and oak savannahs.

Hesston Steam Museum is a great place for the entire family to visit. You can take a ride on a real steam-powered train through the countryside, learn about the history of steam engines that enabled much of the development in these regions, and enjoy refreshments at a restaurant.

Three Oaks Market, in downtown Three Oaks, takes place every Friday afternoon, and it offers the freshest food, produce, and artisanal goods the region has to offer.

Captain Mike's Fun Park in Lake Charter Township is open during summer. This five-acre park offers go-karts, bumper boats, putt-putt courses, snacks, and more.

Fernwood Botanical Garden, slightly inland close to Buchanan, offers wonder, beauty and family fun. On top of a regular arboretum, there is also an adventure garden, nature trails, an education center, and more to enjoy at this beautiful venue.

Did you know? This area is known for its beautiful beaches along Lake Michigan, making it a popular spot for finding Petoskey stones, Michigan's state stone. So see if you can tell the difference between different rocks and find one of these special stones with the little ones!

Things to note: Roads to Harbor Country are in good condition; just be aware of the chance of snow in the winter months.

There are lots of lovely, smaller country lanes in this region that you might want to explore slowly during your trip for views of the rolling hills, forests, and farms.

3. Lake Geneva

1 hour 40 minutes from Chicago (80 miles)

Why visit Lake Geneva with family? Go lake -hopping with your family! This road trip will not only take you to Lake Geneva but also to Lake Zurich and Fox Lake for the ultimate waterside adventure.

Lake Geneva is also a wonderful day trip or weekend destination for the family, including your little ones. With parks and playgrounds, walking trails, beaches, magic theaters and more, there is much to see and enjoy for everyone.

Driving to Lake Geneva from Chicago: Follow I-90 northwest and hop onto IL-53. You will soon reach Lake Zurich. After your visit, your next stop will be Fox Lake, and then US-12 will take you all the way to Lake Geneva.

Our highlights: Walking trails, slides, swings, and picnic tables can be found at Oak Ridge Marsh Park Playground by Lake Zurich on the way to Lake Geneva.

If you wish to head to the beach with your children, Riviera Beach on Lake Geneva is a good option. It is enjoyed by swimmers, sunbathers, hikers, and boaters alike.

At the small Tristan Crist Magic Theater, you can witness magic and illusion shows that are family-friendly and be amazed!

At Lake Geneva Ziplines & Adventures, your family can explore sky bridges and rope courses and take a zip line ride through the forest. The area also includes hiking and biking trails.

Did you know? Famous for its grand estates and as a former retreat for wealthy Chicago families, it's also known for being the birthplace of the tabletop role-playing game Dungeons & Dragons!

Things to note: Tristan Crist Magic Theater is the region's premier entertainment option, and it is a good idea to book tickets in advance if possible.

4. Peru and LaSalle

1 hour 30 minutes from Chicago (100 miles)

Why visit Peru and LaSalle with family? Peru-LaSalle twin cities provide much to enjoy for the entire family, from beautiful natural getaways to historic sites and a vibrant downtown area to explore with shops and restaurants. They are fabulous destinations from Chicago.

La Salle and its twin city, Peru, make up the core of the Illinois Valley. La Salle, or LaSalle, is known for its many historic sites, such as a replica canal boat and the Hegeler-Carus Mansion.

Driving to Peru and LaSalle from Chicago: Head northwest on I-55 and then switch to I-80 to reach LaSalle. Peru is a short drive from here on US-6.

Our highlights: Starved Rock State Park on the Illinois River is known for its sandstone canyons, some of which have waterfalls. The park has many in wooded trails and fascinating wildlife, and there are lovely viewpoints overlooking the river - perfect for a family outing.

Buffalo Rock State Park in LaSalle County contains a riverside bluff and almost 300 acres of nature, with walking trails, camping sites and fabulous picnic sites.

Visit the I&M Canal National Heritage Area to get a real feel of the life of the American frontier. Little ones traveling with you will especially love the 1880s replica Canal Boat and enjoy taking a boat tour of the canal, which starts with a crash course on “Mule Tending 101”!

Hegeler-Carus Mansion, built in 1874, is a grand Victorian-era home of 57 rooms and is a fascinating place to visit with the family. It features fine details all around; on its hand-painted walls and ceilings, beautiful woodwork, chandeliers, and large glass windows.

Things to note: Starved Rock and Buffalo Rock state parks are open all year round. In winter, it can be particularly special to visit Starved Rock State Park, to view the frozen waterfalls.

As with all roads in Illinois, winter months can see the roads covered in snow at times; be aware of this should you be doing the road trip in winter.

5. Milwaukee

Via Kenosha

2 hours from Chicago (110 miles)

Why visit Milwaukee with family? Milwaukee is a beautiful and fun city on the shore of Lake Michigan, home to splendid historical and cultural attractions for the younger members of the family as well as famous breweries for the parents!

Milwaukee is an easy 2-hour drive away and has lovely attractions for family members of all ages to explore, including museums, a zoo, a science center, shops, and great restaurants.

Driving to Milwaukee from Chicago: Follow I-94 heading directly north and then hop on WI-158 to visit Kenosha. Retrace your steps after your visit to get back on I-94 to arrive in Milwaukee.

Our highlights: In Kenosha, on the way to Milwaukee, you can visit the Dinosaur Discovery Museum to view dinosaur fossils - something exciting for all of the family members.

Milwaukee Public Museum is home to natural and human history exhibits. This museum is great to explore with children, and there is also a restaurant and a dining area.

If you want to visit other museums, Discovery World Science and Technology Museum is another must-see destination for families visiting Milwaukee.

Alternatively, you can visit Milwaukee County Zoo, home to over 3000 animals from 350 different species. This popular zoo receives 1,3 million visitors a year!

Did you know? Milwaukee is known for its major league baseball team, the Milwaukee Brewers, and its unique mascot, Bernie Brewer.

Things to note: Milwaukee winters are known to get cold, and driving conditions may be impacted by snow blizzards if you're doing this road trip in winter. Check ahead of time and prepare accordingly. Fortunately, the city has much to offer in warm and colder seasons!

6. South Bend and Mishawaka

2 hours 10 minutes from Chicago (100 miles)

Why visit South Bend and Mishawaka with family? Visiting South Bend and Mishawaka makes for a lovely trip for the family. South Bend is a university town home to affordable restaurants and fantastic playgrounds.

Both South Bend and Mishawaka areas are famous for the wonderful parks and trail systems present here, as well as for museums, galleries, shopping, and historic spots. These include historic parks, sky-high playgrounds, and green areas with beautiful nature trails.

Driving to South Bend and Mishawaka from Chicago: Heading out of the city in the southeast direction, follow I-90 and then IL-2 to drive into La Porte. From here, the same highway will take you to South Bend and then Mishawaka to the east.

Our highlights: Sky Zone Trampoline Park in Mishawaka offers tons of fun indoors. You can buy single-day passes to access the various activities offered at this park. You can expect lots of bouncing, playing, jumping and flipping here!

The entire family can enjoy a day of entertainment at the Strikes and Spares Entertainment Center. Activities available include go-karts, bowling, mini-golf, and bumper cars. Food and drinks are also available and a toddler area for the youngest members of the family.

Potawatomi Zoo is a zoological park in South Bend. There are animal exhibits and educational programs at the zoo, and even train rides available for the family to enjoy.

At South Bend Chocolate Co. Factory you can get behind the scenes and take a tour to explore the factory floor and observe how the best chocolates are made. The perfect way to spend the afternoon, especially if you or your family have a sweet tooth!

Meanwhile, at The History Museum's Kidsfirst Children's Museum, children have a chance to get a close look at the area's local history and the way of life of the pioneers in South Bend.

Central Park is a popular park in Mishawaka, with a splash pad, playground, and the river running through the park with lovely walking trails alongside it.

Did you know? There are a few explanations as to the origin of the name Mishawaka. It may have derived from the local Potawatomi language in which it would have meant "firewood-tree land".

Alternatively, it might come from the name of a local chief's daughter who, long ago, fell in love with a white trader. She was a princess, also giving the city its nickname, the "Princess City".

Things to note: South Bend and Mishawaka area is especially a good choice for a family trip during the winter time, because of the many indoor attractions present here, as well as the opportunity to enjoy ice skating and other outdoorsy winter activities.

7. Holland

Via Indiana Dunes National Park and Michigan City

2 hours 50 minutes from Chicago (150 miles)

Why visit Holland with family? Circling the southern and eastern shores of Lake Michigan, this road trip will allow you to explore the beaches, dunes and scenic sights along the way, and it eventually takes you to unique Holland, with lovely cycling routes, and tulip fields.

Holland is best known for its Dutch heritage, which is visible in the city's identity. For families, there are plenty of fun activities: explore the area's parks for hiking, picnicking, and playing, or go swimming, paddle boarding, or boating on the lake Macatawa that the city surrounds.

Driving to Holland from Chicago: Follow I-90 out of Chicago and follow the coast towards Indiana Dunes National Park and then Michigan City. From here, I-94 and then I-196 will take you to Holland.

Our highlights: Indiana Dunes National Park is an exciting family-friendly destination. It runs for 20 miles along the shore of Lake Michigan, offering plenty of opportunities to explore the coastline and the dunes. This is also a highly biodiverse area, with a mix of forests and vegetation types to admire and hike through.

Washington Park Zoo in Michigan City is full of magic. This historic zoo, spread out over natural hillside terrain, is home to numerous animals that come from conflicting backgrounds and would not be able to live out their lives in the wild anymore.

Instead, the tigers, tamarins, alligators, and many other animals housed here are now great educators about the natural world for children and adults alike.

Holland State Park in Holland is also a great destination if you're visiting with your children. You can observe deer and migratory birds here, and there are also snack shops and a lovely big playground at the park.

Windmill Island Gardens is home to a 250-year-old windmill called De Zwaan. You can also admire tulip fields and gardens in this beautiful destination.

Outdoor Discovery Center is another fascinating attraction. This nature preserve has an educational facility with exhibitions on native animals, and it also has play areas for children.

Did you know? In Holland, Michigan, you really feel at times like you could be in the Netherlands! Each year, a Tulip Time Festival takes place, during which tulips are seen, planted and exhibited around the city.

Things to note: Should you wish to truly admire the wonderful tulips, visit Holland in May when the Tulip Time Festival takes place.

Indiana Dunes State Park is open all year round, though some hiking trails are closed during the winter months.

8. Madison

Via Rockford

2 hours 50 minutes from Chicago (160 miles)

Why visit Madison with family? Madison is an all-around interesting, big city to explore, and it makes a great day or longer vacation destination from Chicago. If you're visiting with your family, there are plenty of indoor and outdoor attractions to enjoy and explore.

With a free zoo, a large farmer's market, plenty of exciting museums and over 250 parks, you will find plenty to do and explore with your family in Madison.

Driving to Madison from Chicago: Out of Chicago, I-90 will take you northwest to Rockford. From here, the interstate will head directly north to Madison.

Our highlights: Discovery Center Museum at Rockford, Illinois, hosts over 250 interactive exhibits and offers fun and educational activities for both children and their parents.

Henry Vilas Zoo in Madison is another great family destination in this beautiful city. The zoo offers free entry and is home to animals from all over the world.

Dane County Farmer's Market runs on Saturday mornings between April and November. This large farmer's market has a superb selection of produce and snacks for the little ones!

Madison Children's Museum is a must-visit attraction if you visit Madison with your children. This museum for children contains exhibits on arts, sciences, history, culture, and much more.

Things to note: The roads between Chicago and Madison are generally kept in great condition. Of course, if doing this road trip during winter months, you'll need to be prepared for snowy conditions on the roads.

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Family-friendly weekend trips from Chicago (3-5 hours each way)

Have a holiday that conveniently coincides with a Monday? Then, these weekend and long weekend trips from Chicago will be amazing drives to enjoy with your family. From charming coastal towns to buzzing cityscapes, you will have plenty of options to choose from.

9. Galena and Chestnut Mountain Resort

3 hours from Chicago (170 miles)

Why visit Galena and Chestnut Mountain Resort with family? This road trip takes you to the fascinating city of Galena, with great attractions for the entire family to explore. You will also get to enjoy great skiing and snowboarding at the nearby Chestnut Mountain Resort.

Galena attracts around a million visitors each year to admire its old-town charm, cobbled streets, and historic buildings, stroll through the city's many antique shops and wineries, or explore the hilly country surrounding the Mississippi River.

Driving to Galena and Chestnut Mountain Resort from Chicago: You will follow I-90 from Chicago until you reach Rockford and then hop onto US-20 to head into Galena. From here, W Blackjack Road will take you to Chestnut Mountain Resort.

Our highlights: When taking this road trip from Chicago, we recommend stopping at the Discovery Center Museum in Rockford on the way to explore their 250 interactive exhibits and workshops.

Once you arrive in Galena, you can take in the views and listen to the stories of the historic Galena on a city tour provided by Galena Trolley Tours.

P.T. Murphy Magic Theater offers an intimate, magical performance experience at a small 24-seat private theater in the historic heart of Galena.

Chestnut Mountain Resort, on a ridge overlooking the Mississippi River, offers skiing and snowboarding slopes for all levels. The resort also offers river cruises, an indoor pool, restaurants, and wonderful lodging options.

Things to note: The drive to Galena from Chicago along US-20 is generally a smooth one, just be prepared for snowy conditions in the wintertime.

Galena itself offers much to see and do in all seasons, and in winter, the historic city is adorned in colorful Christmas decorations, which only make the atmosphere more cheerful and festive!

It is good to book tickets in advance for the P.T. Murphy Magic Theater show because the theater only has 24 seats.

10. Sheboygan and Manitowoc

Via Milwaukee

3 hours from Chicago (175 miles)

Why visit Sheboygan and Manitowoc with family? If you're traveling to Sheboygan and Manitowoc with your family, you're in for a treat on the western shores of Lake Michigan. You'll find a great array of attractions and activities to enjoy here, from scenic parks and beaches to engaging museums and water parks.

Sheboygan is especially known as the outdoor enthusiasts' heaven because of its location and geography: it is dubbed the world's Freshwater Surf Capital, and Lake Michigan also offers much else to a visitor in the form of fishing, sailing, and long sandy beaches. Manitowoc is also known for water-based activities and attractions.

Driving to Sheboygan and Manitowoc from Chicago: Follow I-94 until you reach Milwaukee and then switch to I-43 to visit Sheboygan and then Manitowoc.

Our highlights: On the way to Manitowoc, you might want to stop at Milwaukee to visit the large Milwaukee County Zoo. The accredited zoo is home to over 2,000 animals from more than 300 species and is a great learning experience for families.

Bookworm Garden in Sheboygan is a beautiful, playful botanical garden inspired by popular children's books.

Show Family Playground is a large, well-equipped playground in Sheboygan. This all-inclusive playground has various unique features - great fun for the children of the family.

At the Wisconsin Maritime Museum, you can learn about the maritime history of the Great Lakes region. There are ship models, boats, a WWII submarine, and more to explore at this fascinating museum.

Cedar Crest Ice Cream Factory & Parlor is one landmark destination in Manitowoc. Meet the giant cow standing in front of this popular ice cream parlor, and have a seat outside to enjoy your favorite flavors of ice cream.

Did you know? Sheboygan is dubbed the "Bratwurst Capital of the World," so get ready to enjoy this delicious sausage in all shapes and forms during your visit here.

Things to note: As with other family road trips from Chicago, be aware of possible snowy driving conditions, traffic, and adverse weather if making this road trip in the winter months.

11. Indianapolis

3 hours from Chicago (185 miles)

Why visit Indianapolis with family? Indianapolis is home to well-known sporting events and locations, a range of historic sites and districts, various museums and monuments, and fun attractions.

Indianapolis has a not-too-large, walkable downtown area, and various attractions suitable for the entire family. This makes it a great weekend destination away from Chicago at any time of the year.

Driving to Indianapolis from Chicago: Follow I-94 south out of Chicago and hop onto I-65 to reach Indianapolis.

Our highlights: The Children's Museum of Indianapolis fosters a sense of discovery through its learning experiences and exhibits in that focus on science, arts, and humanities.

Indianapolis Zoo is actually a zoo, an aquarium, and a botanical garden all in one. It is home to over 1,400 animals and nearly 50,000 plants! It is a wondrous place for all the family members to explore.

Visit Rhythm! Discovery Center in downtown Indianapolis; here, you and your children can explore the world's only drum and percussion museum. You may admire historical artifacts or experience and try various hands-on percussion instruments.

If you and your family prefer to spend time outdoors, you can view beautiful nature and interactive art installations at Virginia B. Fairbanks Art & Nature Park.

Did you know? Indianapolis hosts the annual automobile race Indianapolis 500 - the world's largest single-day sporting event. Other well-attended, popular sporting events also take place in the city, one example being another racing event, Brickyard 400.

Things to note: Do check the opening times of Rhythm! Discovery Center, for the attraction, has usually been closed on specific days of the week.

Though Indianapolis doesn't get as much snow as many other long-winter cities, it is still good to be prepared for snowy driving conditions or snowfall during your outings if visiting the city in the winter months.

12. Saugatuck and Grand Rapids

Via Benton Harbor and South Haven

3 hours 20 minutes from Chicago (185 miles)

Why visit Saugatuck and Grand Rapids with family? This road trip takes you northeast along the shores of Lake Michigan, past lovely small towns and scenic landscapes, to the unique, fascinating cities of Saugatuck and Grand Rapids.

The cities offer much to see and do for children and adults. Saugatuck is known for its award-winning beaches, thriving art scene, and scenic waterways, while Grand Rapids is home to fabulous museums and galleries and also a number of wonderful craft breweries.

Driving to Saugatuck and Grand Rapids from Chicago: You will basically follow the shore of Lake Michigan, heading northeast on this road trip. Take I-90 from Chicago and then switch to I-94 and I-196, which will take you all the way to Saugatuck and Grand Rapids.

Our highlights: Visit Sarett Nature Center in Benton Harbor, where you can walk along meandering nature trails, enjoy observation platforms, participate in nature classes, or admire live animals and a butterfly house.

South Haven Lighthouse, in South Haven on the way, is a beautiful, historic place to take a walk with your family.

You'll find many beaches on your drive up towards Grand Rapids. In Saugatuck, Oval Beach is perhaps the most popular - and historic - beach. White sands and blue waters, nestled in sand dunes and bordered by the Kalamazoo River, present a wonderful opportunity to spend a day out swimming, picnicking, or exploring nature.

Grand Rapids Public Museum offers adventure and fun on three floors. You'll find history and science exhibits here, as well as a historic carousel, a theater, and a planetarium.

Frederik Meijer Gardens & Sculpture Park in Grand Rapids is visited by hundreds of thousands yearly. This botanical garden also has an art museum and an outdoor sculpture park.

Things to note: Winters in these areas of Michigan are known to get very cold, and you might also do well to prepare for possible icy conditions on the roads if making this road trip during the colder season.

13. Wisconsin Dells

3 hours 10 minutes from Chicago (200 miles)

Why visit Wisconsin Dells with family? Wisconsin Dells is a great destination to visit with family. It is especially well known for its many fun and adventurous water parks and for the stunning scenery of forests and gorges to be admired on the Wisconsin River.

Driving to Wisconsin Dells from Chicago: Follow I-90 northwest to Rockford and then to the outskirts of Madison in the north. The interstate will then take you directly to Wisconsin Dells.

Our highlights: About 10 minutes from downtown Wisconsin Dells, Noah's Ark Water Park is one of the largest water parks in the US. Your children (and yourself!) will love the exciting water slides and endless fun to be had at this famous park.

Take a boat tour to view the Dells of the Wisconsin River. These tours leave from the heart of Wisconsin Dells and take you to view mesmerizing glacier-carved gorges and sandstone formations.

Mt. Olympus Water and Theme Park is another fabulous family destination. Inspired by ancient Greece, this theme park has a water park section and a classic theme park section with rides and rollercoasters.

Mirror Lake State Park has wetlands, swimming beaches, trails, and camping facilities. In the summer, you can go boating and canoeing on the lake, and in the winter, skiing and snowshoeing are possible activities.

Did you know? Known as the "Waterpark Capital of the World," Wisconsin Dells a paradise for visitors of all ages. You will find over 20 indoor and outdoor waterparks here during your visit!

Things to note: At Mirror Lake State Park, some of the campsites and facilities are only open during the summer months.

READ MORE - Road Trip from Chicago to Wisconsin Dells

14. Door County

4 hours 30 minutes from Chicago (270 miles)

Why visit Door County with family? For a very scenic road trip, head up north from Chicago to Door County. It is a fabulous weekend or longer vacation destination for the family, with beautiful views, beaches, family-friendly attractions and farmer's markets.

Door County on the Door Peninsula offers spectacular views over Green Bay on one side and Lake Michigan on the other. The area is known for picturesque coastal towns, fruit orchards, lighthouses, and scenic views.

Driving to Door County from Chicago: Head directly north out of Chicago, following the coast of Lake Michigan on I-94 and I-43 until you reach the outskirts of Manitowoc. From here, drive to Green Bay on the interstate and then hop onto WI-54 to reach Door County.

Our highlights: On the shore of Lake Michigan stands Door County's most iconic lighthouse, Cana Island Lighthouse. Explore the island, including the light tower and lighthouse keeper's home.

Peninsula State Park on the shores of Green Bay is a popular camping destination, which is also great for swimming, hiking, biking, or just slowly driving through the park to view the high bluffs and sandy beaches.

The Farm Historic Living Museum in Sturgeon Bay is a great place for children or adults to visit. Here, you can view exhibits on rural farming and heritage and visit farm animals and bottle-feed baby animals in natural farm surroundings.

Don't forget to get on the ferry to cross Death's Door to get onto Washington Island. Children will enjoy the 30-minute ferry ride and explore the island with nature to view, as well as shops and restaurants.

Did you know? Door County is famous for its cherries and is a popular place to go cherry picking. These cherries usually reach their peak ripeness from mid-July to mid-August, when you and your family can experience the joy of picking your own fresh produce.

Things to note: Though Door County is obviously a beautiful, activity-filled summer holiday destination, it is also wonderful in winter. You can do skiing, snowshoeing or ice fishing, and even, if you're lucky, view the northern lights that are often seen here due to less light pollution than elsewhere in Wisconsin.

Just be aware that, although there will always be attempts to keep roads clear during the snowy periods of the winter months, plowing may take some time; it is good to be prepared with proper winter tires and gear if making this road trip in the cold season.

The Farm Historic Living Museum is not open during the months of November until May.

15. Ann Arbor and Detroit

4 hours 30 minutes from Chicago (285 miles)

Why visit Ann Arbor and Detroit with family? This road trip takes you from Chicago by the shores of Lake Michigan to Detroit, on the shores of Lake St. Clair. Museums, amusement parks, outdoor adventures, parks and Detroit Zoo are but some of the examples of child-friendly things to do in this vibrant city.

On the way to Detroit, Ann Arbor is another fabulous place for a stopover; it is especially known for its many interactive, science-focused activities and attractions.

Driving to Ann Arbor and Detroit from Chicago: A road trip from Lake Michigan to Lake St Clair, follow I-94 heading east to reach Ann Arbor. The switch to M-14 and I-96 to arrive at Detroit.

Our highlights: Ann Arbor Hands-On Museum and Leslie Science & Nature Center is a must-see destinations in Ann Arbor for families with children. This museum has engaging, interactive exhibits and activities on various scientific fields and topics.

Detroit Zoo has over 2,000 animals living on its 125 acres of various habitats. The zoo features many award-winning exhibits such as the Wildlife Interpretive Gallery, the Great Apes of Harambee, and the Arctic Ring of Life.

Detroit is known as the automobile capital of the world; Henry Ford built his first car here in 1896, and the city led the manufacturing of cars in this part of the US in the early 20th century. Nowadays, various automobile museums in Detroit are a testimony to this history.

Henry Ford Museum of American Innovation commemorates the life and accomplishments of this famous entrepreneur. The museum features various exhibits on the history of automobiles, and children can take part in interactive games and activities.

Visit Greenfield Village to experience 90 acres of preserved historical buildings, interactive activities, and costumed characters related to Detroit's living history. You can even ride on a horse-drawn carriage or a steam-powered train.

At C.J. Barrymore's play park, you'll find lots of family-friendly fun, from golfing, go-karts, and bowling to thrill rides, video games, and laser tag.

Did you know? Detroit is well known as the birthplace of the distinctive Motown Sound.

Things to note: Be aware of traffic while traveling to Detroit with your family; the large city's streets may experience heavy traffic at times, and conditions can be especially difficult during the snowy winter months. Even Interstate 94, leading to Detroit, can be affected due to snowy or icy conditions during winter.

16. Cincinnati

Via Indianapolis

4 hours 40 minutes from Chicago (300 miles)

Why visit Cincinnati with family? This beautiful riverside city is called "Paris of America" due to its stunning architecture and fantastic museums and theaters.

If you're visiting Cincinnati with your family, some of the fun things to do together include riverfront parks, a zoo, a botanical garden, and museums.

Driving to Cincinnati from Chicago: Head southeast following I-94 and I-65 to reach Indianapolis. From here, switch to I-74 to arrive in Cincinnati.

Our highlights: On the way to Cincinnati, visit the Children's Museum of Indianapolis, the world's largest children's museum. There are over five floors of exhibitions on dinosaurs, space stations and more.

Located on the banks of the Ohio River, Cincinnati is a city known for its arts, world-class breweries, a lovely riverfront, and beautiful 19th-century buildings.

Cincinnati Zoo & Botanical Garden has a large variety of animals, habitats, and gardens to explore. It is dedicated to adventure, education and conservation.

Highfield Discovery Garden at Glenwood Gardens has a variety of activities and adventures for families. There is a fantasy playground where you can explore fairy gardens, a butterfly garden, and trains.

Kings Island is a famous amusement park near Cincinnati. It contains various rides, rollercoasters, water parks, and play areas.

Did you know? Cincinnati is the city where the first concrete skyscraper of the whole world was built; Ingall's Building, finished in 1903. Another first for the city is that the first professional baseball team ever came from here, the Red Stockings of Cincinnati.

Things to note: Take some basic measures to stay safe on the roads if you're making this road trip in winter; have proper winter tires and take it easy in the traffic.

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Longer family-friendly trips from Chicago (Over 5 hours each way)

Mid-semester breaks or any other holidays mean having more time to spend with your family! From visiting incredible zoos to admiring world-famous waterfalls, longer road trips from Chicago can be the ultimate family road trip adventure.

17. Sandusky and Cedar Point Amusement Park

Via Fort Wayne

5 hours 40 minutes from Chicago (315 miles)

Why visit Sandusky and Cedar Point Amusement Park with family? This road trip first takes you to one of the biggest cities in Indiana, Fort Wayne, where you can visit amazing family attractions such as a children's zoo and a botanical conservatory.

You'll then continue on to the shores of Lake Erie, to beautiful Sandusky, a place with miles of sunny beaches, lovely nature trails, world-class amusement parks, and interesting arts and architecture.

Driving to Sandusky and Cedar Point Amusement Park from Chicago: Head to Fort Wayne from Chicago on US-30 driving southeast. Then hop onto US-24 towards Toledo and switch to I-90 past Waterville. From here, you will drive on OH-4 to reach Sandusky and Cedar Point.

Our highlights: Fort Wayne Children's Zoo is arguably one of the best zoos in the country. Here, you can have close-up experiences with over a thousand animals housed at the zoo.

Cedar Point Amusement Park is located on Lake Erie Peninsula in Sandusky. It is the second-oldest amusement park in the country, operating since 1870.

Less expensive than its counterparts in the larger cities of the US, Cedar Point contains 70 amazing rides, as well as restaurants, hotels, and a waterpark. Please keep in mind that the waterpark has a separate entry.

The Merry-Go-Round Museum in Sandusky contains a historic 1939 Allan Herschell carousel, beautiful historic artifacts and a gift shop, all related to this world-famous, beloved amusement park ride.

Hungry for know knowledge? The Maritime Museum of Sandusky contains exciting exhibits on boats, pirates, and shipwrecks. This is the perfect for any pirate-loving young members of the family to visit.

Pipe Creek Wildlife Area, consisting largely of wetlands, is a beautiful place to do birdwatching and walks in nature. You can enjoy a nice walk here with your family once you have had your fill of all the amazing rides and museums this road trip has to offer.

Did you know? Cedar Point is known as "The Roller Coaster Capital of the World," thrilling for adventure-seekers of all ages!

Things to know: Visiting Cedar Point Amusement Park may turn out cheaper if you book tickets in advance online, rather than buying at the entrance.

18. St Louis

Via Peoria and Springfield

5 hours from Chicago (335 miles)

Why visit St Louis with family? St Louis is a fabulous vacation destination for the family, over a long weekend or a longer stay; the city area contains amazing public parks, as well as several free attractions suitable for families with children.

On the way to St Louis, you can stop at Peoria to enjoy the many family-friendly activities here or explore historic sites and attractions in Springfield.

Driving to St Louis from Chicago: Following I-55 southeast of Chicago, use Exit 163 and then 101 to reach Peoria. After your visit, head south on I-155 to Springfield and switch to I-55 to reach St Louis.

Our highlights: On the way to St Louis, Peoria PlayHouse, a children's museum, is worth visiting. It features interactive exhibits on arts, sciences, and music.

Also on the way, you can explore the historic sites of Springfield, including the Abraham Lincoln Presidential Library and Museum. You and your family can learn about history through interactive displays and films.

A must-stop and exciting activity once in St Louis is visiting Gateway Arch. You can ride the tram up to take in views of the Mississippi River and the surrounding city from the top of this 630-foot tall steel structure, or you can visit an interactive museum on site with history exhibitions covering 200 years.

Citygarden Sculpture Park is another lovely destination for a family with children in St Louis. During your visit, you can enjoy beautiful trees and nature, view art displays, and splash in shallow pools and waterfalls. There are food trucks serving food and drinks as well.

Saint Louis Science Center has over 700 interactive exhibits covering various topics. Both children and adults will enjoy a day of exploration and fun at this center. General admission is free; you only pay for certain special exhibits and the IMAX Theater.

Did you know? St Louis is home to many firsts: the first commercial peanut butter was sold here, the first kindergarten in the US was operated in St Louis, and the city was also the birthplace of products such as ice cream cones, 7up, and ice tea.

Things to note: Should you wish to take the tram to the top of Gateway Arch when visiting here, booking tickets in advance is a good idea, as they're often sold out on the busier days.

READ MORE - Road Trip from Chicago to St Louis

19. Cleveland and Cuyahoga Valley National Park

5 hours 50 minutes from Chicago (365 miles)

Why visit Cleveland and Cuyahoga Valley National Park with family? Visit Cleveland with your family to wander through the many city parks and nature areas of this "Forest City", as Cleveland is lovingly nicknamed.

The surroundings of Cleveland, along the shores of Lake Erie, also include beautiful scenic spots and beaches to enjoy.

Driving to Cleveland and Cuyahoga Valley National Park from Chicago: Heading east from Chicago, follow I-90 all the way to Cleveland and then dip south to visit Cuyahoga Valley National Park.

Our highlights: On the way to Cleveland, you can stop at beautiful Toledo by Lake Erie. At the riverfront, you'll find Imagination Station, a hands-on science museum that has over 300 exhibits for children and curious minds to explore.

Cleveland Museum of Art is a truly fascinating and awe-inspiring place, with over 30,000 works of art spanning 5,000 years of history from around the world.

The Rock and Roll Hall of Fame is fun to explore with the whole family. There are interesting artifacts of famous musicians, such as Jimi Hendrix's guitar and John Lennon's bed. Exhibitions with mature themes are marked, which helps if you visit with children.

At the Cleveland Museum of Natural History, you and the family can enjoy fascinating sections such as a dinosaur exhibit, an earthquake simulator, and a live animal wildlife center.

Cuyahoga Valley National Park, close to Cleveland, is home to beautiful landscapes of forests, rolling hills, farmlands and the winding Cuyahoga River. You can explore and learn about the history of the Ohio & Erie Canal or admire the native plants and wildlife.

Did you know? Superman was born in Cleveland! At least in the sense that the creators of the beloved character created the early Superman prototype while still in high school here, in 1933.

Things to note: I-90 from Chicago to Cleveland is generally in great condition. Of course, be aware of traffic during busy periods, and be prepared for snowy conditions if you're doing the road trip in winter.

Though not required, it is best to book tickets in advance online for attractions such as the Rock and Roll Hall of Fame and the Cleveland Museum of Natural History.

READ MORE - Road Trip from Chicago to Cleveland

20. Minneapolis and the Mall of America

6 hours 20 minutes from Chicago (420 miles)

Why visit Minneapolis and the Mall of America with family? This relatively longer road trip from Chicago offers opportunities to visit Madison and Eau Claire on the way. Minneapolis, known for its parks and lakes, is the perfect mix of urban sophistication and natural beauty.

Just walking around the city is an experience in itself; the city is located on the scenic banks of the Mississippi River, and Minneapolis offers both architectural and natural gems to admire.

Driving to Minneapolis and the Mall of America from Chicago: You will be heading northwest on this road trip from Chicago on I-90, which will take you past Madison and Wisconsin Dells before you merge onto I-94. Follow this interstate to reach Minneapolis and the Mall of America.

Our highlights: On the way, you can make a stop at Eau Claire to visit the Children's Museum. It includes imagination-spurring activities and exhibits, such as a construction zone, a miniature city, Water Works, and a Body Parts area.

Walker Art Center in Minneapolis, connected with the Sculpture Garden, contains exhibits of contemporary art. It can be a great way to introduce children to contemporary art, for the center offers activities especially geared towards children.

Minnehaha Park is an old and popular park in Minneapolis. It contains lovely nature trails, and the stunning Minnehaha Falls waterfall is a well-known attraction.

You could easily spend a whole day exploring the Science Museum of Minnesota, located in St Paul, Minneapolis's twin city across the river. It offers four stories of science-related fun, and the interactive exhibits include a news center, "quackery museum," and IMAX theater.

Mall of America is an amazing shopping mall. As one of the biggest shopping malls in the country, it might not be surprising to see more than 500 stores during your visit to the mall!

There are also 50 restaurants and plenty of great activities for the family - the most famous is the Nickelodeon Universe, an indoor amusement park that fits entirely within this enormous mall.

Things to note: If you wish to visit Minneapolis in winter, there is plenty to do, as well as in the summer months; the city's many indoor attractions take care of that.

Just remember to be cautious if traveling on snowy roads during the winter months, and be prepared with proper equipment.

READ MORE - Road Trip from Chicago to Minneapolis

21. Niagara Falls

Via Cleveland

8 hours 30 minutes from Chicago (560 miles)

Why visit Niagara Falls with family? Niagara Falls is a bucket-list destination and is a great place to visit with family. The drive to Niagara Falls from Chicago is lovely as well, with options to stop at diverse cities and nature areas on the shores of Lake Erie.

At Niagara Falls, not only can you visit the world-famous waterfall and view it on a boat tour, but you can also explore beautiful walks, great museums, a waterpark, and a butterfly conservatory in the city.

Driving to Niagara Falls from Chicago: Although this is a longer road trip on our list, it is quite a straightforward drive. Simply follow I-90 from Lake Michigan shores to Lake Erie coastline and head northeast until you reach Cleveland, and then follow this interstate to Buffalo.

From here, head north on I-190 to reach Niagara Falls.

Our highlights: Cleveland is a great stop on the way from Chicago to Niagara Falls. Cleveland Museum of Natural History has exciting exhibits for people of all ages to enjoy, from a dinosaur exhibit to an earthquake simulation and a wildlife center.

A must-see when visiting Niagara Falls is, of course, the famous waterfall. It is said to be best viewed from the Canadian side or from Skylon Tower, so if you have your passports with you, you can see for yourself and decide!

On the USA side, the Maid of the Mist Boat Tour will take you as close as possible to the thundering waterfalls. You'll don a poncho and sail into the heart of the falls, experiencing the mist, roar, and sheer power of Niagara Falls. Please note that these tours can be seasonal and check before visiting.

Cave of the Winds Tour will take you to the base of the Bridal Veil Falls, where you can explore the wooden walkways just a few feet away from the cascading water. The highlight is the "Hurricane Deck," where you can experience tropical storm-like conditions.

On the Canadian side, the Skylon Tower is a 764-foot-tall observation tower with an arcade and a revolving restaurant. It offers magnificent views of the waterfall and the surrounding city.

While in Canada, you can also visit the Niagara Butterfly Conservatory. Wander through this tropical paradise and view its plants, flowers, and over 2,000 butterflies. You can watch an introductory video and take your time to meander through the garden.

Did you know? Beyond its breathtaking natural beauty, it's also known for daredevil stunts, like tightrope walks across the falls.

Things to note: Niagara Falls waterfall can be magical to view in winter as well! Then, parts of the falls freeze over, and special light displays further increase the enchantment of the falls.

Though not absolutely necessary, booking tickets to Skylon Tower in advance is recommended.

READ MORE - Road Trip from Chicago to Niagara Falls

22. Dollywood, Gatlinburg and Great Smoky Mountains National Park

Via Louisville

9 hours 20 minutes from Chicago (590 miles)

Why visit Dollywood, Gatlinburg and Great Smoky Mountains National Park with family? This scenic road trip will take you south from Chicago, through the states of Indiana and Kentucky, into Tennessee and the Great Smoky Mountains National Park.

he national park is full of stunning trails, viewpoints, and picnic spots. Gatlinburg is an attraction-filled mountain town and a gateway to the nearby national park. You can also visit the Dollywood theme park for fun and thrilling experiences on the way.

Driving to Dollywood, Gatlinburg and Great Smoky Mountains National Park from Chicago: Heading out of Chicago on this longer drive, use I-94 and then I-65 to drive through Indianapolis and then Louisville. Switch to I-75 past Lexington to arrive at your destination in Knoxville.

After your visit, follow I-40 to Dollywood and then Gatlinburg, your gateway to the beautiful Great Smoky Mountains National Park.

Our highlights: In Louisville, there are many unique attractions to visit. These include the Kentucky Derby Museum and Louisville Mega Cavern, where you can enjoy fully underground aerial rope challenges, ziplines, and adventure tours.

Dollywood, owned by Dolly Parton, is full of enchanting attractions, from rollercoaster rides and waterparks to children's playgrounds and country restaurants. What better way to start your family road trip?

Be ready to be astonished at Ripley's Aquarium of the Smokies in Gatlinburg, where you can admire over 10,000 exotic sea creatures spread over ten themed galleries.

Ober Mountain is another fantastic place to visit in Gatlinburg. This mountainside amusement park offers minigolf, wildlife encounters, and hiking in summer, and skiing and snowboarding in winter, and you can enjoy stunning views over the Great Smoky Mountains National Park any season of the year.

Great Smoky Mountains National Park is a vast, beautiful area to explore. Take a picnic in the forest, view wildlife, and explore the rivers and waterfalls. It will be an experience to remember for the entire family.

Did you know? While exploring the Great Smoky Mountains, you may encounter a diverse range of wildlife: there are over 4,000 plants, 65 species of mammals, 200 species of birds, nearly 70 species of fish, and over 80 species of reptiles and amphibians that call this region home.

The national park is also called the "Salamander capital of the world," for the park is home to 30 different species of salamander!

Things to note: Great Smoky Mountains National Park is open year-round, although certain visitor facilities will be closed in winter.

Be extra careful and prepared with the correct equipment on the mountainous roads of this region if making this road trip in winter.

23. Orlando

Via Atlanta

18 hours from Chicago (1,160 miles)

Why visit Orlando with family? This epic, longer road trip from Chicago is the perfect one to do with older children and will take you south through various states, past several buzzing metropolises into sunny Florida and Orlando, a theme park capital of the world.

Take your time with the family to stop at the various cities and nature areas along the way. Enjoy the landscapes of rolling hills around Louisville and the forests of Tennessee and Georgia, and visit the various attractions in cities such as Nashville and Atlanta.

In Orlando, you can spend days and days exploring the various theme parks around the city, the most famous of which are perhaps Walt Disney World Resort, Universal Orlando, and Legoland.

Driving to Orlando from Chicago: The road trip from Chicago to Orlando is the longest on our list, but it is fairly easy to follow as most of the driving will take place on the interstates.

From Chicago, head south through Indianapolis and Louisville on I-65 until you reach Nashville. From here, hop onto I-24 and then I-75 past Chattanooga. This interstate will take you all the way into Florida, Florida's Turnpike will then take you to Orlando.

Our highlights: Atlanta is one of the many amazing places to stop on this road trip. In Atlanta, we recommend visiting the stunning Atlanta Botanical Garden. It is a world of magic and beauty, with unique plant centers, features, and gardens.

Walt Disney World Resort is one of the most popular attractions in Orlando. This entertainment resort complex is a world of magic and fun, home to four theme parks and two water parks.

Universal Orlando also has famous attractions, rides, and live shows. Our favorite places to visit here with family are the Wizarding World of Harry Potter and the Minions section, but maybe you will discover a new favorite!

Did you know? Did you know that Walt Disney World Resort is about the same size as San Francisco? This vast theme park is Florida's most popular tourist destination, attracting almost 60 million people every year. The park offers something to everyone, whatever your age or background!

Things to note: It is a good idea to book tickets to Orlando theme parks in advance to avoid any disappointments or waiting times.

READ MORE - Road Trip from Chicago to Orlando

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