8 Best Things to Do in Chicago in Winter

Midway Plaisance Ice Rink is located in Hyde Park and offers a family-friendly skating rink with skating lessons, pickup games of hockey, and special events all season long. This stretch of park is on the campus of the University of Chicago, on the exact spot where the first-ever Ferris wheel stood at the 1893 Chicago World's Fair. In addition to the ice rink, the park offers a warming centre. Here, you can duck inside to escape from the cold for a while and get warm again before heading back out for some more wintry fun on the skating rink.

The Peninsula Sky Rink is situated atop a 4-star hotel in the heart of city centre along Michigan Avenue and offers breathtaking views of the skyline surrounded by elegant lights. The rink itself is on the fourth-floor terrace and features displays of snowflake lights and trees aglow with holiday spirit. The rink isn't the only attraction here, however; besides skating and looking down upon the bustling city streets, you can head for an outdoor chalet that offers comfort food like beignets and mulled cider. Skate rental is included in the cost, and the admission benefits local charities for kids.

Soldier Field Sledding Hill is on the parkland surrounding Soldier Field and offers a 33-foot, lightning-fast slope that's ideal for thrill-seeking sleigh riders. Even on days when it's warmer out and the rest of the city is thawed, the park service uses snow machines to ensure that the hill is always properly covered. From the top of the hill, you can enjoy a panoramic view of Lake Michigan before you roar down the slopes at pulse-pounding speeds. Since it's so close to Soldier Field, that means there's also plenty of nearby shopping, dining, and indoor spots to warm up.

The Chicago Park District controls all the city parks, more than 8,800 acres of public space, and oversees all of the winter events that take place in these spaces. Amongst the most popular winter activities in the Chicago parks are the ice-skating rinks, and there are a number of these from which to choose. Other events include intro to ballet workshops, holiday craft-project workshops, wreath-making courses, winter drawing courses, and other arts-and-crafts classes to appeal to all ages. Even Santa gets into the fun with hosted breakfasts, bingo with Santa, storytime sessions, and others.

Northerly Island is a man-made peninsula on Lake Michigan, just to the east of Soldier Field, that offers special holiday events and snowshoeing along nature trails. Hikers can get out into the wilderness and engage in winter bird- and wildlife viewing while snapping photos of the Chicago skyline in the distance. Of course, during the Polar Adventure Days events, visitors can learn to make winter crafts inspired by nature and get up close and personal to wolves, huskies, and raptors. Best of all, Polar Adventure Days are completely free, making it a great option for family fun.

The Lincoln Park Conservatory is a botanical garden that's open all year long inside an elegant and historic Victorian glasshouse where you can see colourful exotic plants. The plants on display here are from all over the world, and not only does this offer a splash of brightness in the winter, but it's also a welcome escape from the cold. The Conservatory is located in Lincoln Park and is one of the oldest public gardens in the city, having opened in the 1870s. Outside the glasshouse, you can see timeless sculptures like the Schiller Monument and the Eli Bates Fountain.

The Lakefront Trail offers an escape from the hustle and bustle of the holiday season with over 18 miles of path along Lake Michigan for biking, walking, and recreation. The trail is paved and easy to navigate — no snowshoes necessary. If you're looking for a bit of peace and quiet when the city gets crowded with shoppers, this could be a good option. Water fountains and bathrooms are positioned along the trail for convenience. The trail also separates the bike trail from the pedestrian one, so you won't have to worry about getting in someone's way.

Winterland at Gallagher Way turns the iconic Wrigley Field into a massive wonderland of holiday activities, from an 8,000-square-foot ice rink to classic holiday film presentations. Santa Claus puts in appearances and hosts breakfasts to bring more family fun to the table, and you can also take curling or skating lessons. Of course, no wonderland is complete without a market, and the Christkindlmarket offers dozens of speciality shops where you can find that perfect handmade, one-of-a-kind gift for your loved one. Speaking of crafts, you can take a wreath-making workshop to decorate your own wonderland.