Chicago becomes a winter wonderland over the holidays, offering dazzling displays of holiday lights, exciting sledging hills, live entertainment and, of course, ice skating.

These classic and iconic winter pastimes are on full display, including a full-fledged holiday extravaganza in the town square, where you can watch public screenings of seasonal films and certainly get a visit from Santa Claus. You can catch live musical performances or just grab your favourite inflatable ring, toboggan or sleigh and hit the slopes.

So, what are the best things to do in Chicago during the winter?

  • 1

    Midway Plaisance Ice Rink

    Skating in Hyde Park

    Midway Plaisance Ice Rink
    • Adventure
    • Budget
    • Couples
    • Families

    Midway Plaisance Ice Rink is located in the neighbourhood of Hyde Park and offers a family-friendly skating rink with skating lessons, 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.

    Location: 1130 Midway Plaisance, Chicago, IL 60637, USA

    Open: Daily during the winter months from 12 pm to 7 pm

    Phone: +1 312-745-2470

    Map
  • 2

    The Peninsula Sky Rink

    Ice rink above Michigan Avenue

    The Peninsula Sky Rink
    • Adventure
    • Couples
    • Families

    The Peninsula Sky Rink is situated atop a 4-star hotel in the heart of downtown along Michigan Avenue, and offers breath-taking 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 Christmas 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. Check the opening times before you head out to avoid disappointment. 

    Location: 108 E Superior St, Chicago, IL 60611, USA

    Phone: +1 312-337-2888

    Map
  • 3

    Soldier Field Sledding Hill

    Purpose-built sledding hill next to the iconic stadium

    Soldier Field Sledding Hill
    • Adventure
    • Couples
    • Families

    The Soldier Field Sledding Hill is on the parkland surrounding Soldier Field and offers a 70-metre, lightning-fast slope that’s ideal for thrill-seeking sled 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.

    Location: Museum Campus, Chicago, IL 60605, USA

    Map
  • 4

    Chicago Park District

    Winter activities all over the city

    Chicago Park District
    • Budget
    • Couples
    • Families

    The Chicago Park District controls all the city parks, more than 8,800 acres of public space, and oversees all the winter events that take place in these spaces. Among 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, story time sessions, and more.

    Map
  • 5

    Northerly Island

    Nature trails and winter crafts

    Northerly Island
    • Adventure
    • Budget
    • Couples
    • Families

    Northerly Island is a man-made peninsula on Lake Michigan, just to the east of Soldier Field, that offers special winter 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.

    Map
  • 6

    Lincoln Park Conservatory

    Exotic flowers and timeless sculptures in a Victorian park

    Lincoln Park Conservatory
    • Budget
    • Couples
    • Families

    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, which is also known as Storks at Play.

    Location: 2391 N Stockton Dr, Chicago, IL 60614, USA

    Open: Wednesday–Sunday from 9 am to 5 pm (closed Monday–Tuesday)

    Phone: +1 312-742-7736

    Map

    photo by Alanscottwalker (CC BY-SA 3.0) modified

  • 7

    Lakefront Trail

    A trail that follows the shores of Lake Michigan

    Lakefront Trail
    • Adventure
    • Budget

    The Lakefront Trail offers an escape from the hustle and bustle of the winter season with almost 30 kilometres of path along Lake Michigan for biking, walking and recreation. The trail is paved and easy to navigate, so no snowshoes necessary. If you’re looking for a bit of peace and quiet when the city gets crowded with shoppers, this could be the spot for you.

    Water fountains and bathrooms are positioned along the trail for your convenience and comfort. The trail also separates the bike trail from the pedestrian one so you can go at a pace that works for you, whether that’s on wheels or your own two feet.

    Read more
    Map
  • 8

    Winterland at Gallagher Way

    A winter village within Wrigley Field

    Winterland at Gallagher Way
    • Families
    • Shoppers

    Winterland at Gallagher Way turns the iconic Wrigley Field into a massive wonderland of holiday activities, from a 750-square-metre ice rink to classic Christmas 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 Christkindlmarkt offers dozens of specialty 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 create a decoration for your own wonderland.

    Read more

    Location: 3635 N Clark St, Chicago, IL 60613, USA

    Phone: +1 773-388-8260

    Map

    photo by Jay Clark (CC BY 2.0) modified