Best Winter Road Trips From Chicago

🚗 350 miles ⏱️ 5 hours, 40 minutes

This is a year-round resort to visit, but with 140 inches of snow, it comes into its own during winter! The extensive and varied ski slopes here are great for a wide range of skiing abilities.

🚗 590 miles ⏱️ 9 hours, 55 minutes

Seeing the famous falls cascading through the snowy ground is a truly magical experience – and one that's different from any other trip you might take. Head across the border on this road trip to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake.

🚗 825 miles ⏱️ 14 hours, 20 minutes

New York City puts on an amazing holiday display – from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow.

🚗 305 miles ⏱️ 5 hours, 25 minutes

As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices.

🚗 190 miles ⏱️ 3 hours, 15 minutes

As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park.

🚗 950 miles ⏱️ 16 hours

The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter.

🚗 155 miles ⏱️ 2 hours, 55 minutes

This beautiful little lakeside town hosts a magical Christmas market every year. It's also a great place to enjoy fabulous snow-based activities

🚗 720 miles ⏱️ 13 hours

As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter.

🚗 145 miles ⏱️ 2 hours, 40 minutes

Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota.

🚗 1,145 miles ⏱️ 18 hours

The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year.

🚗 790 miles ⏱️ 13 hours, 20 minutes

Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. Visitors and locals alike flock to the Macy's Light Show, running for over half a century, and the charming Dickens Village, also found at the store.

🚗 180 miles ⏱️ 2 hours, 55 minutes

From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town.

🚗 530 miles ⏱️ 9 hours, 30 minutes

With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip. Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer.

🚗 83 miles ⏱️ 1 hour, 40 minutes

A short but sweet trip! Take to the snow for an active day outside, then relax at a beautiful spa. This popular vacation town is also less crowded in winter compared to the summer months.

🚗 945 miles ⏱️ 15 hours, 35 minutes

Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment.