Top Family-Friendly Winter Activities In Chicago

From ice skating to Christmas markets, discover the best family-friendly activities to enjoy this winter in Chicago.

Winter is a wonderful time to bring your family to Chicago. Yes, it’s cold. Yes, it’s snowy and icy. But it’s also cosy, welcoming, and full of holiday spirit. From ice skating beneath the sparkling skyline to warming your hands on spiced hot chocolate in the winter markets, Chicago in winter is a wonderland that will enchant your whole family.

Here are some of the best family-friendly winter activities to enjoy in Chicago.

Planning your winter escape to Chicago

Before we launch into Chicago’s many winter activities, let’s set you up for the best possible trip with some pre-travel planning advice. It’s important to pick your travel dates carefully. Winter in Chicago typically runs from December to March, and temperatures can drop to the 20s and 30s (lower with wind-chill factor). So, if you want to see the Christmas lights and markets, plan your winter break for December, and if you’re heading to the Windy City in January or February, be sure to pack warm clothing that you can layer up in harsh winter weather.

Bear in mind that, while the city is good at salting and gritting the sidewalks, it is a bit harder to get around the city in snowy and icy weather. This is important to consider when you’re trying to find a hotel in Chicago. Ideally, you want to be close to the main attractions you want to visit, so you don’t have to spend too much time walking home through wintry conditions, or battling the L Train gates in all your clumsy winter gear.

Now, with that advice out of the way, let’s dive into the fun stuff: Chicago’s top family-friendly winter attractions.

Ice skating

What could be more magical than skating in the snow, surrounded by the glittering skyline of one of the world’s greatest cities? Chicagoans love ice skating and take every opportunity to set up ice rinks when temperatures drop. One of the best – the McCormick Tribune Ice Rink – can be found in Millennium Park, where you can skate to the backdrop of the gleaming ‘Bean’ sculpture. Best of all, admission is free if you bring your own skates (if you don’t, you can rent some on site for a small fee).

Right next door to this, you’ll find the Maggie Daley Park Skating Ribbon. Unlike the traditional pond-shaped skating rink, this is a skating path that winds between snowy trees and gentle hills. It’s a fantastic, novel skating experience that’s very popular with children.

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Navy Pier

Navy Pier has lots to see and do at all times of the year, but it comes into its own during the holiday season. From (roughly) Thanksgiving through to New Year’s Eve, Navy Pier hosts the Light Up The Lake Festival – a spectacular winter event with all the lights, food, music, views, and fun you could imagine. You and your kids can indulge in everything from ice skating surrounded by light sculptures to admiring the twinkling skyline from the warmth of the Centennial Wheel. 

Even if you’re not here during the Festival, Navy Pier is still a great venue to visit during winter. There are great views over Lake Michigan and Chicago, a funfair, arcades, and a huge range of dining options. If the temperatures are really bitter, the Chicago Children’s Museum gives you the opportunity to get out of the cold and enjoy a thoroughly child-centric cultural experience.

Holiday experiences

Chicago really pulls out all the stops during the holidays. At Daley Plaza, the famous Christkindlmarket sets up from late November to just before Christmas. You can find all kinds of interesting stocking-stuffers, trinkets, and ornaments here – but even if you’re not interested in Christmas shopping, the market is well worth a visit. It’s a thoroughly festive experience, with music, lights, and wonderful smells from the roasted nuts, gingerbread, bratwurst, spiced cider, hot chocolate, and more on offer.

For unbeatable light displays, stroll along Michigan Avenue, which outdoes itself every year with the Magnificent Mile Lights Festival. Or wind down with a wander through the Chicago Botanic Gardens, which puts on an enchanting lightscape every year. 

If your kids want to see Santa, you’ll find him hanging out in a range of malls and department stores throughout the city. Just follow the reindeer and elf signs!

Indoor activities

Travelling with kids during the colder months is harder than travelling alone. Small people feel the cold more than adults do, and, no matter how well you wrap them up or how well they’re enjoying the outdoors, it’s inevitable that your kids will want to get in the warm at some point. Luckily, Chicago has plenty of indoor activities for the whole family to enjoy. Here are a couple of suggestions.

• Shedd Aquarium, the Field Museum, and Adler Planetarium are all within walking distance of one another. If your kids are chilly after ice skating at Millennium or Maggie Daley, take a brisk walk to the Museum Campus and warm up in one or several of these iconic Chicago attractions.
• The Lincoln Park Zoo has plenty of warm indoor habitats to enjoy during the winter, as well as a great Zoolights display that runs from late November through early January.
• Chicago is famous for its food, and restaurants are especially welcoming during the winter. Let yourselves be ushered in out of the cold and warm up from the inside with some of the best food that the USA has to offer. 
• Legoland Discovery Center, a short drive from central Chicago, is a mostly indoor day out that’s fun for the whole family. 

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Make lasting holiday memories with a winter trip to Chicago

Chicago comes alive during the holiday season, with lights, music, markets, festivals, and more. But even if you’re visiting in the cold months outside the holidays, there’s still plenty to do and see with your family in Chicago. If you’re looking for an urban winter escape that’s actually enhanced rather than reduced by the weather, you can’t go wrong with Chicago.

There you have it! The best family-friendly activities to enjoy in Chicago in winter! What would you add to the list?