When you think about sledding in Chicago, you might assume that you’ll need to head out of the city limits. The city of Chicago isn’t exactly known for its hills. However, there are some incredible sledding hills in Chicago that provide a unique city experience. Take a look at our guide to sledding in Chicago, then arrange a Skydeck visit to warm up.
Sledding Hills in Chicago
When you’re looking for places to go sledding in Chicago, turn to our excellent city parks system. That’s where you’ll find the best sledding hills in Chicago without having to make a long drive. They’re also home to some of our best outdoor ice skating rinks.
Cricket Hill: 4500 N. Lakeshore Drive
Located at the north end of Lincoln Park, this relatively steep, four-sided hill offers incredible views of Lake Michigan near Montrose Beach. Buy tickets in advance for the Lincoln Park Zoolights Festival and make a day and evening of it.
Dan Ryan Woods: 83rd St and Western Avenue
As part of the Forest Preserves of Cook County, the Dan Ryan Woods (located in the southwest part of the city) has the tallest sledding hills in the area. They even feature views of the Willis Tower and Chicago skyline. The hills are big enough to offer snowboarding opportunities, too.
Soldier Field: 1410 S Museum Campus Drive
No snow? No problem! Head to the 220-foot sledding hill at the north end of the stadium’s south parking lot, where man-made snow is provided, so you can keep sledding into March.
Palmisano Park: 2700 S Halsted Street
From trash to treasure on the near South Side! Known as “Mount Bridgeport”, this elevation offers skyline views on what was first a limestone quarry and then a landfill.
Warm Up Post-Sledding at Skydeck!
After an exhilarating day sledding down Chicago’s best hills, there’s no better way to warm up and extend your winter adventure than by visiting Skydeck Chicago at Willis Tower. Located just a short drive from most sledding spots, Skydeck offers breathtaking views, interactive exhibits, and a one-of-a-kind experience that makes it the perfect post-sledding destination.
Unparalleled Views from 1,353 Feet Up
Step inside Willis Tower and take a ride up to the 103rd floor, where you’ll be greeted with panoramic views of Chicago’s winter wonderland. From up here, you can see up to four states on a clear day and get a completely new perspective on the city’s snow-covered landscape.
Experience The Ledge—If You Dare!
For an added adrenaline rush, step out onto The Ledge, a series of glass-floored balconies that extend 4.3 feet outside the tower. It’s a heart-pounding experience that lets you look straight down 1,353 feet to the bustling streets below—a must for thrill-seekers and adventure lovers!
Interactive Museum & Chicago History
Before heading up, take some time to explore Skydeck’s interactive museum, which showcases Chicago’s history, architecture, and culture. It’s a great way to warm up while learning about the city’s iconic skyline and fascinating past.
Delicious Dining at Catalog
Need to refuel? Head to Catalog, the dining and retail space at Willis Tower, where you’ll find a variety of restaurants and cafés to grab a hot meal or a warm drink before or after your Skydeck experience. Whether it’s a cozy cup of hot chocolate or a full meal, you’ll find plenty of options to satisfy your post-sledding appetite.
Make It a Full Winter Adventure
Pairing sledding in Chicago with a visit to Skydeck makes for the ultimate winter day—fun, adventure, and stunning city views all in one! Whether you’re a local looking for a new winter tradition or a visitor exploring the best seasonal activities, this combination guarantees an unforgettable experience.
Plan your visit today to our Chicago attraction and make this winter one to remember! Book your Skydeck tickets in advance to skip the lines and make the most of your day in Chicago.