10+ Family Winter Fun Activities in Chicago

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10+ Family Winter Fun Activities in Chicago, Illinois

If your family is looking for a fun holiday or winter getaway, look no further than Chicago, Illinois. The windy city is a great place for families of all ages to play and explore in the winter months. We love to gift experiences to our children and this past Christmas we gifted them a trip to Chicago full of fun over winter break! It was their first time experiencing a BIG city and they had so much fun taking in three full days of big city life.

Although it is the winter season, it does not mean you cannot enjoy some of the fun outdoor activities that Chicago offers! Bundle up and embrace the chilly weather with some of these fun outdoor activities. There are hundreds of things to see, do, and eat in Chicago but we are sharing some of the best things we did during our December stay.


Radisson Blu Aqua Hotel in Downtown Chicago

The Radisson Blu Aqua Hotel was really the perfect option for our family. When you entered the hotel lobby the entire hotel was decked out with holiday decorations and even included a fun mailbox to drop a letter off for Santa. We loved the spacious rooms with gorgeous views (we had a view of Lake Michigan and the Chicago River), the lobby with comfy chairs and TVs (we had game night and pizza one evening), and the pool was perfect for the kids! In addition, we were right next to Millennium Park, the Chicago River, and a short walk to Michigan Avenue. Between all the amazing amenities and location of Radisson Blu Aqua Hotel, we were so happy we chose to call it home during our stay in Downtown Chicago.


Field Museum

The Field Museum is a must for any history buff and if you are experiencing some snowy days in Chicago, plan a trip! There are several exhibitions that change regularly, so there is always a reason to return. They regularly offer free days. Take a look at their calendar before your trip.

Jack Frost’s Pop-up Winter Walk & Christmas Tree Farm

If you are visiting Chicago during the holiday season, a stop at Jack Frost’s Pop-up is a must! This entire pop-up is full of the holiday spirit including decorated Christmas trees and light displays, a full-size ice skating rink (they offer skate rentals), carnival games, festive drinks (booze-up that hot chocolate!), bumper cars, and ax-throwing. There is fun for the entire family. If you are an Instagram junky, there are a ton of places to grab the perfect picture. The location provides a beautiful backdrop of Downtown Chicago too!

Visiting Chicago outside of the holiday season? This company has various themed pop-ups throughout the year including Neon Summer and Jack’s Pumpkin Pop-Up.

Lincoln Park Zoo

The Lincoln Park Zoo is open 365 days a year and offers free admission. Who can pass up a free zoo?! There are several buildings to explore. The perfect way to warm up during cold weather while exploring the zoo and visiting with animal friends.

Michigan Avenue

Whether you are planning to do a ton of shopping, or not you must experience walking down Michigan Avenue aka The Magnificent Mile. This stretch in Downtown Chicago is full of shopping, food, entertainment, and holiday lights during the holiday season. The kids loved taking in all the big buildings, the people, and the experience of it all. We made our way down Michigan Avenue with one goal in mind … Water Tower Place. One of the main gifts for our daughter was a bucket list visit to the American Girl Doll store.

Note: Plan a trip earlier in the Winter season and catch the annual Magnificent Mile Lights Festival.

Millennium Park

Millennium Park located in Downtown Chicago is a free outdoor activity full of possibilities. Walk around and snap a picture next to the popular attraction, Cloud Gate (aka “The Bean”), different art exhibitions, walkthrough Lurie Garden (which may not be super pretty in the Winter), catch the beautiful lights on the giant Millennium Christmas Tree, and other winter programming. If you know when you will be visiting, jump online and make reservations to ice skate at McCormick Tribune Ice Rink. Spots fill quickly! Bring your own skates or rent ice skates.

Maggie Daley Park

Maggie Daley Park is just across the way from Millennium Park and offers the best attractions for young audiences. Experience the climbing wall, play garden, mini-golf, and more. Visiting during the warmer months? You can rent rollerblades, micro scooters, and bungees to experience the park.

Navy Pier

You cannot visit Chicago without a trip to River North Chicago to Navy Pier. Navy Pier is home to the Chicago Children’s Museum (indoor activity!), fun restaurants, the Centennial Wheel, carnival games, shopping, and more. You can easily spend an entire day at this Chicago attraction full of fun for the whole family. If visiting during the holiday season do not miss Light Up the Lake. This seasonal event provides an indoor light-sculpture experience with ice skating, beer garden, Christmas lights, kiddie train rides, appearances from Santa Claus, and so much more.

Shedd Aquarium

The Shedd Aquarium is one of the best in the Midwest and one of my favorite Chicago attractions. I have always been a huge fan of whales, dolphins, sea lions, and more. You will not regret your visit. Do not forget to catch a live show of some of their animals showing off their tricks and skills during your visit. We had a lot of fun!

Willis Tower

Catch a glimpse of Chicago from above! The perfect place to do so is at the Willis Tower Skydeck. The Willis Tower is the third tallest building in the Western Hemisphere. Step out on the glass and feel like you are literally floating above the city at 1,353 feet in the air.


Giordano’s Pizza

Giordano’s Pizza is a must when traveling to Chicago. They are famous for their stuffed deep-dish pizza. Dine in, carry out, or have your pizza delivered. We enjoyed a fun game night in our hotel lobby while indulging in this yummy pizza.

JoJo’s Shake Bar

If you love sweets and ice cream, JoJo’s Shake Bar is a dream come true. They offer lunch options, over-the-top shakes, fun cocktails, boozy shakes, and a super fun atmosphere. My kids loved the giant Lite-Brite on the wall that kept them busy. During the holiday season, they offer a Winter Wonderland at their River North location.

Stan’s Donuts & Coffee

If you are in Chicago you will more than likely come across Stan’s Donuts & Coffee. They are considered the BEST donuts in Chicago. They are over-the-top and super fun. We made a stop before we started our day and it was so good! They offer coffee, donuts, and other breakfast items as well.

Wildberry Pancakes & Cafe

Wildberry Pancakes & Cafe was a short walk from our hotel and right across the street from Millennium Park. We made an entire morning walking to breakfast, then exploring the park. Their food was incredible and they get busy super fast, so plan for a wait.


Erin Huiatt

Erin is a reliable resource and stepping stone for women and families to find support and make connections within our community. She wants families to feel confident to reach out and ask for help and advice to get pointed in the right direction. She enjoys traveling and exploring with her two children in tow!

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