Winter in the Windy City is a funny thing. It’s long, it can definitely be brutal (I’ve been living that this past week! #theflusucks), but we all endure these winter months because this city is still so special, even despite the crazy weather! Plus, the snow makes the city look like a real-life snow globe ?
That being said, whether you live here or are just visiting, it can be tough to figure out what to do there are a lot of winter activities to do. As long as you have waterproof boots and a good winter coat, you can focus on how Chicago is a snowy winter wonderland!
15 Things To Do In Chicago In The Winter
1. Go Ice Skating
I know this might feel like a holiday activity, but there’s no reason why you can’t go ice skating the rest of winter, too! The Skating Ribbon in Maggie Daley Park, along with the ice skating rink in Millennium Park are both open through early March (weather permitting). Both are free, and you can pay for skate rentals if you need them. The ribbon winds through the park, whereas the rink is located right in between The Bean and the skyline.
2. Try curling at The Gwen
Did you know that The Gwen Terrace has curling?! It’s a non-traditional rink (not made of ice), but you can still play a game with a fireplace, fire pit, heat lamps, and lounge seating all around. You can also order off of their amazing menu while you’re up there. Make your reservation here.
3. Walk through the zoo
The Lincoln Park Zoo is definitely more fun when it’s warm out, but it’s still a beautiful place to go for a stroll on a bright and sunny winter day! As long as it’s not totally freezing out, it can be really nice to say hi to the polar bears, snap a picture of the skyline at the bridge, and then maybe duck into the Lincoln Park Conservatory to warm up 😉 Also, if you’re here around the holidays, don’t miss ZooLights (their holiday lights festival!).
4. Shop on Michigan Avenue
I only really recommend this one for out of towners because Magnificent Mile can be a little overwhelming… but if you’ve never been to Chicago before, it has really great shopping! Plus, it’s the perfect mix of indoor and outdoor time when it’s freezing outside. Walk a bit, then try on all the shoes at Nordstrom! Then walk a little bit more, and then check out the new Starbucks!
5. Go on a winter weekend getaway
A few years ago, we spent a weekend at the Grand Geneva and it was SO FUN. We went skiing on their “mountain top” (perfect for people who like to ski, but don’t need huge Colorado mountains!), ate dinner at their lovely restaurant, and generally just enjoyed being cozy in our beautiful villa. HIGHLY recommend!!
6. Make reservations during Chicago Restaurant Week
Winter in Chicago can feel very long, especially once the holidays have passed. Luckily, Chicago Restaurant Week is the BEST excuse to change out of your sweatpants and get excited about leaving your apartment again! From January 24 – February 9, 2020, over 400 restaurants offer special menus that are $24 for brunch and lunch, and $36 and/or $48 for dinner. It’s the best. (Check out my favorite Chicago Restaurant Week menus here!)
7. Go to a museum
Chicago has some incredible museums – and the cold weather is the perfect excuse to spend an afternoon at one (or more!) of them. My personal favorites? The Field Museum (remember this shoot on the steps?!) and The Art Institute of Chicago! Both are insanely gorgeous inside with great exhibits – and they’re both in really iconic parts of the city. The view from The Field Museum, Adler Planetarium, and Shedd Aquarium is one of my favorites in the whole city. The Museum of Science and Industry, the Chicago History Museum, and the Museum of Contemporary Art are also great options, too! (Don’t forget to check out Free Museum Days for Illinois residents, too!)
8. Go to a Broadway in Chicago show
Can’t make it to New York to see a Broadway show? Don’t worry – Broadway in Chicago brings the National Tours to us! Sometimes the shows are here for just a few weeks and other times they stay longer (like Hamilton!), so just be sure to check the dates for the shows that interest you. I already can’t wait to get tickets to Frozen next winter!
9. See a local show
In addition to the big productions that come to our city, Chicago also has a world class theatre scene of our own. I’m actually going to see Emma at the Chicago Shakespeare Theatre on Navy Pier in a few weeks! Their shows are always so well done – whether it’s a Shakespeare show or a musical! (That’s where I saw SIX: The Musical ?) A few other favorites: Steppenwolf Theatre (Gary Senise is a co-founder!), Lookingglass Theatre (David Schwimmer is a co-founder!), and The Goodman Theatre (the oldest and largest non-profit Chicago theatre).
10. Gather your friends for a night at Second City
I probably could have combined this with local shows, but a night at Second City is so different from a night at a play… and it’s a VERY Chicago thing to do 😉 Grab a drink and peruse all of the famous alumni on the walls and enjoy a night of hilarious improv!
11. Go to an Arcade Bar
This one is fresh in my mind because we just went to Replay in Lincoln Park last weekend and it was such a blast! Not only do they have tons of games, but they also have a whole Friends setup! Episodes on the tv, life size cutouts of the actors, the couch and the door… it’s really cute ? There’s also a Replay in Lakeview, Emporium in West Loop/Logan Square/Wicker Park, and Headquarters in River North.
12. Cheer on the Blackhawks
If you’ve never been to a Blackhawks game, I HIGHLY recommend getting yourself there this winter. There’s nothing quite like singing along to Chelsea Dagger after they score a goal. It’s such a fun experience!
13. Walk around the Garfield Park Conservatory
Missing greenery and nature in your life? The Garfield Park Conservatory is a bit of a hike if you live on the North side, but it’s only a short drive from the West Loop… and it’s SO PRETTY. It also happens to be one of the largest greenhouse conservatories in the country. So cool.
14. Brave The Skydeck (Willis Tower)
Tourists and locals can all get excited about The Skydeck. I mean, standing 1,353 feet up in a glass box that extends 4 feet out over the city is thrilling for ANYONE! The 103rd floor of the Willis Tower also has interactive exhibits and, of course, incredible views. General Admission tickets are $26 for adults and $18 for kids.
15. Go to the Observation Deck at 360 Chicago
Not into The Ledge, but still want the city views? 360 Chicago in The John Hancock Building has some of my favorite views of the city, especially the lake and the beaches! You can listen to their audio tour and then grab a drink at the bar to make an afternoon out of it. They also have a new activity for the daredevils called TILT. I haven’t done it yet… I feel like it looks scarier than The Ledge at Willis Tower does!
Winter Holidays And Festivals
If you’re reading this around the holidays, I have a roundup of The Best Holiday Activities in Chicago!
What are your favorite winter activities?
Even though this isn’t specific to Chicago, I also love hosting game nights during the winter. I’ll cook something for the group, we’ll open some wine, and we’ll play some games! (Exploding Kittens and What Do You Meme are our favorites!) What about you?!