Winter in Illinois can be brisk, but the payoff is often worth it. From Chicago’s ice rinks and holiday lights to snow-dusted trails, ski slopes, and small-town main streets, the state offers a wide range of cold-weather experiences for travelers willing to bundle up.
To help you plan, here at Traveling Lifestyle, we’ve selected 10 Illinois winter destinations that make the cold worth it. Let’s dive in.
Old Ryan’s Red Round Barn
Located in the scenic Johnson-Sauk Trail State Park in Illinois, Old Ryan’s Red Round Barn transforms into a picturesque winter landmark. Its striking red color sharply contrasts with the serene, snow-covered landscape of the park, attracting photographers and history enthusiasts.
Villa Olivia
Situated in the Chicago suburbs, Villa Olivia is a convenient option for urban residents seeking winter fun. This community-focused ski resort offers seven runs, a snow tubing hill, and beginner lessons for skiers and snowboarders.
Though smaller in scale compared to other resorts, Villa Olivia’s proximity to Chicago and affordable pricing make it a popular choice for first-timers and families. The on-site restaurant provides a cozy retreat after a day on the slopes.
Matthiessen State Park
Matthiessen State Park, located near Oglesby, offers a quieter alternative to some of northern Illinois’ more heavily visited winter landmarks, with trails that feel notably more secluded once temperatures drop.
The park is defined by its rugged sandstone formations, steep stairways, and narrow canyons—features that become especially dramatic in winter, when snow highlights the rock contours and ice gathers along ledges and creek beds.
For hikers prepared for cold-weather conditions, Matthiessen delivers a scenic, photogenic outing with a strong sense of place, where the landscape’s texture and scale are often at their most striking in the off-season.
Springfield
The first thing that probably comes to your mind when you hear “Springfield” is the hometown of the Simpsons. You might not find Homer or Lisa here, but with its long history, it will surely not disappoint.
Visit the Abraham Lincoln Presidential Library and Museum, Dana Thomas House, designed by Frank Lloyd Wright, or discover the local coffee and craft beer scene. This Springfield is much more fun than the one on TV.
Galena & Eagle Ridge Resort and Spa
Once home to Civil War General and U.S. President Ulysses S. Grant, Galena is a charming historic town near the border with Iowa.
The whole town is packed with sights, including museums, distilleries, and galleries, but it also makes a perfect home base for some winter fun.
Snowboarders and skiers can go to Chestnut Mountain Resort. It has 19 slopes, snowboarding and skiing lessons for beginners, as well as a café and a restaurant to enjoy some après-ski.
On the other hand, for snowshoeing or cross-country skiing, set off to the Nordic Center at Eagle Ridge Resort and Spa.
Snowstar Winter Park
If winter sports are what you’re looking for, Snowstar Winter Park is another fantastic choice. It’s set near the Quad Cities, and so it’s easily reachable. It’s family-friendly and has skiing lessons available for all abilities and levels.
There are 15 trails, 11 snow tubing lanes, and a huge freestyle terrain. There are also plenty of dining and lodging options which make every possible visitor satisfied.
Great Wolf Lodge Annual Celebration
For a family-friendly winter getaway, Great Wolf Lodge in Gurnee provides an indoor water park, themed activities, cozy accommodations and a special annual winter celebration. It’s an ideal destination for escaping the cold while keeping the kids entertained.
Garden of the Gods, Shawnee National Forest
Are you looking to spend some time far away from the hustle and bustle of the city? We’ve got you covered. With its jaw-dropping views, Garden of the Gods is a crowd-pleaser, and it’s even more majestic in winter.
There are over 21 miles of trails to hike and the terrain isn’t difficult. But be careful, the stones can sometimes get slippery under the snow, so make sure to wear a suitable pair of shoes.
Chicago
Chicago is a popular destination all year round. But in winter, it boasts plenty of activities no other season permits and is, therefore, definitely worth a stop.
To get in the festive mood, visit the rooftop of The Gwen where you can try some nice cocktails with a view. You can also cozy up at the heated beer garden at Kaiser Tiger.
Wanna get moving with your precious half? Maggie Daley Park offers a very romantic ice skating experience. Due to its popularity, it tends to get rather busy, so even if you bring your own skates, a reservation is required.
Starved Rock State Park
Need some adrenaline in your bloodstream? There is no better place to engage in ice climbing than in Starved Rock State Park. It features 4 climbable canyons – Wildcat Canyon (90+ ft), LaSalle Canyon (20+ feet), Ottawa Canyon (35. ft), and Tonti Canyon (60+ ft). But note, they are all for experienced climbers only.
Are you a beginner? In that case, we recommend you head to the Nice Ice Tower in Monee. The 35-foot tower is man-made and suitable for all levels.
