25 Things to Do in Chicago In The Winter (From a local!)

Looking for things to do in Chicago in the winter?

Visiting the city and are wondering if you should avoid the entire Midwest? Are you a local dreading the start of winter and scrambling to figure out how you’re going to get through the next few months?

Look no further! Introducing a list of 25 Things to Do in Chicago in the Winter (By a Local!) that will make sure that you are warm and cozy this upcoming season. Turn the snow from foe to friend and have fun falling in love with the city of Chicago all over again.

Note: none of these links are sponsored! I’ve been living in Chicago for 5 years and enjoy spending time in the city (yes, even in the winter). However, it did take me a few years to figure what activities best crack that dark and dreary seasonal depression. Please enjoy a little sample of everything!   

Table of Contents

Outdoor Activities in Chicago

(1)   Maggie Daley Ice Skating Ribbon

Okay, let’s start with outdoor activities first, because I know everyone wants to get them out of the way to get back home and stay indoors for the rest of the day. On this list, we only have three outdoor activities. For starters, nothing says winter like ice skating. There are a lot of fantastic ice-skating rinks across the city such as Midway Ice Skating Rink or Millennium Park Ice Rink, but my absolute favorite is the Maggie Daley Ice Skating Ribbon. Not only is this rink centrally-located in downtown Chicago (also known as the Loop), but whereas other ice-skating rinks are shaped like traditional ovals, Maggie Daley is a ribbon! This unique shape takes you through a course surrounded by trees, bushes, and a fantastic view of the skyline. Ice skate rentals are only $5, and if you own your own pair, enjoy a completely free session!

(2)   Lincoln Park Zoo & ZooLights

As someone from Washington, D.C., I was pleasantly surprised to see that the Lincoln Park Zoo is free, just like the Smithsonian museums. During the day, you can meet sea lions, polar bears, and other furry friends who are enjoying the snow more than you are. At night, for just $10, enter the park to see the amazing ZooLights exhibition. They truly do a fantastic job of turning the entire park into a spectacular light show. The best part is that all of the money goes towards conservation efforts and care for the animals.

(3)   Northerly Island Polar Adventure Days

Exact days for 2024 have not been released yet, but every year, the city hosts Polar Adventure Days at Northerly Island. Offered just two Saturdays in January and February, this is a great way to get out and enjoy the outdoors in downtown Chicago. The city brings in reindeer, sled dogs, and allows patrons to go snowshoeing or sledding. While the activities are geared more towards children, even adults can enjoy this slice of nature just steps away from the Loop.

 

Chicago Museums

 

(4)   Shedd Aquarium

Welcome to Museum Campus, an area of Chicago that houses quite a few museums right along the picturesque shoreline of Lake Michigan. The Shedd Aquarium is a popular favorite because of all the animals to meet on a snowy afternoon. Come face-to-face with penguins, dolphins, beluga whales, and a whole cast of slippery characters. Shedd tickets require advanced purchase, averaging around $35 per adult.

(5)   Field Museum

The Field Museum in Chicago’s version of a natural history museum, with a resident dinosaur named SUE and a bunch of other fantastic exhibitions. Just last week, I wrote a blog post about 15 Things to Do in London, where I mentioned the British Museum and paying a visit to the Egyptian mummies. However, if London is too far away, check out the mummies at the Field Museum instead!

 

(6)   Adler Planetarium

Adler Planetarium is the United States’ very first planetarium, a great place to see exhibits on astronomy and astrophysics. Founded in 1930 by a local named Max Adler, the Planetarium sits at the Northern tip of Northerly Island, offering fantastic views of Lake Michigan – and if luck is in your favor – of clear skies. On Wednesdays, the planetarium hosts the Adler After Dark event, where you can wander the exhibits from 4 to 10pm. Better yet, it is free for Illinois residents.

(7)   The Art Institute of Chicago

Another Chicago classic is the Art Institute, one of the world’s largest and oldest art museums. Admission is $32 which grants you entrance into a collection of different exhibits. The official Art Institute website has a great page on what to see in an hour, including modern art, sculptures, and their signature miniature rooms. As a blogger who focuses on fast travel and highlights to prioritize, seeing this page made me happy! If you are also interested in zooming through and optimizing your time, definitely check out that link.

 

(8)   Museum of Science and Industry (MSI) and a walk around Hyde Park

The Museum of Science and Industry might be the most underrated museum in all of Chicago. While it’s not located in the downtown Loop area, it does give you an excuse to venture into the historic Hyde Park neighborhood. This is the home of the University of Chicago (my alma matter!) and a beautiful campus with many coffee shops that are worth exploring. When the snow has just fallen and is undisturbed, UChicago’s campus is a true winter wonderland. As for the MSI, notable exhibits include indoor storms, one of five U-boats left in the world, and a hall featuring forms of transportation and giant locomotives.

Sports Games in Chicago

 

(9)   Basketball  – Bulls

Gone are the days of sunny baseball games and crisp fall football games. Enter watching sports indoors under the comfort of a roof. Head over to the United Center to watch the Bulls play. The Bulls are Chicago’s men’s basketball team, and tickets cost approximately $50. Check here for the Bulls schedule.

 

(10)   Hockey – Blackhawks

Luckily, Blackhawk games are also hosted at the United Center. If you’re down to camp out, why not watch multiple games in one weekend? The Blackhawks are Chicago’s hockey team, and these fast-paced games are incredibly fun to experience. Even those who aren’t fans of the game itself will greatly enjoy the buzz of the ambiance. Check here for the Blackhawks schedule.

 

Indoor Activities in Chicago

 

(11)   Thrifting in Wicker Park

Now, I don’t see this option in nearly enough lists of things to do in Chicago, so I definitely wanted to include this. Thrifting is a fantastic way to get indoors and lose yourself within all the rows of clothing. If you’re like me, you will have no idea how to properly find the best deals, but it is still a fun way to kill a few hours in the warmth. If you’re lucky, you will only spend a few bucks on cool finds. Wicker Park is considered the best neighborhood for thrifting, and I would suggest checking out Village Discount and Ragstock.

 

(12)   Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest botanical conservatories in the United States. While the grounds are over 100 acres, there are a full 2 acres of indoor display houses. After wandering the outdoor gardens, go inside to see the Palm House, the Fern Room, the Desert House, and so much more. Reservations are required in advance but are completely free.

(13)   Catch a Broadway Show

Before you say, ‘hey, isn’t Broadway just from New York?’, enter Broadway in Chicago, the city’s premier theater production company. With five historic theatres mostly in the downtown area, you can see all of the classics that rotate through New York, such as Hamilton, Wicked, and The Lion King. The best part? The price for a ticket is far better than anything you will get in the big apple.

 

(14)   Catch a Comedy Show

Nothing says Chicago like a good comedy show on a snowy Friday night. The Second City and Laugh Factory are two of the most popular options in the city with both stand-up and improv shows. Check out a full list of The Second City shows here and Laugh Factory here.

(15)   Go to a Drive-In Movie

For those of you lucky enough to have a car in Chicago to beat the freeze instead of waiting for the train, try heading to a drive-in movie this winter! Of course, this activity is not suitable on a subzero night as you have to turn your car completely off, but if there happens to be an unusually warm evening and sitting in your car with a blanket sounds like a fun idea, head to ChiTown Movies in Pilsen. ChiTown Movies charges a flat rate of around $33 per car, and if you take a group of friends, you can split that cost pretty easily. In even more amazing news, you can get food delivered to your car so you don’t have to unravel yourself from the blankets when you start to crave warm popcorn and a Jarritos soda.

 

(16)   Try an Escape Room

Let’s keep it rolling with more indoor activities! Why not try an escape room? Fox in a Box is the self-proclaimed best escape room in Chicago, and I will have to agree with that. You can get a private room for you and your friends so you don’t have to puzzle-solve with strangers. This Fox in a Box location includes the following themed rooms: Bank, Zodiac, Prison, and Bunker.

 

(17)   Explore Navy Pier

Navy Pier is a carnival-like zone along the shoreline of Lake Michigan in Chicago’s Streeterville area. Locals both loathe and love Navy Pier, as the summer crowds are hard to beat, but there is always an activity for everyone. Winter is a great time to visit because even though you’ll miss out on summer fireworks and outdoor carnival attractions, you can ride the Ferris wheel with no line! Indoors, explore the food hall and countless shops inside the mezzanine. It may come as a surprise, but Navy Pier also hosts incredibly funny renditions of Shakespeare comedies. See here for what they’re offering at the Chicago Shakespeare Theatre on Navy Pier.

Food & Bars in Chicago

 

(18)   The Green Mill

The Green Mill is a destination that is a hidden gem among millennials and Gen-Z folk, but boomers and older residents are well-aware of this fantastic bar! The Green Mill has been around since 1907 and hosts a free comedy show on Saturdays called the Paper Machete. The cozy nature of the bar really makes it a fantastic spot to hit on a cold weekend. Make sure to arrive super early – the show begins at 3pm but seats fill up almost an hour before.

(19)   Try Trivia at a Bar

Ask Chicagoans what their favorite winter activity is, and I bet that most will say that they partake in weekly trivia. Nearly every night during the week, some bar across Chicago is hosting a trivia evening. This is a great activity to hunker down and have a beer without falling asleep incredibly early. While you probably won’t know the answer to a lot of these questions, it’s always a great way to spend a weekday evening instead of watching Netflix! Check out a bunch of events hosted by whaddayaknow, but note that this is certainly not an extensive list of all the pubs doing quizzes throughout Chicago.

 

(20)   Cozy Hot Pot in Chinatown

While Chicago’s Chinatown is nothing like the sprawling neighborhood of San Francisco, it is a perfect size for the winter as it is cozier and smaller. Spanning only a couple of central blocks, Chinatown is easily accessible by train. On a cold winter evening, splurge on a good hot pot meal. Happy Lamb is a popular option for large groups and celebrating festivities. However, I am a big fan of Spicy Grandma Kitchen because of its more authentic and laid-back experience.

 

(21)   Hit a Curling Bar

All right, I might’ve tricked you with the placement of this particular bar. Yes, I did put it under the bar section, but I will say that you might have to be outside during most of the night. Yet, I promise that the novelty of curling at a bar will warm you up! Book your own personal curling arena for the evening and enjoy drinks with friends. We love Whiskey Business and Upstairs at the Gwen.

(22)   JoJo’s Shake Bar

JoJo’s Shake Bar is more of an experience than a bar and is the epitome of a winter wonderland. Their festivities extend way past Christmas, bringing cheer to your February. The atmosphere is incredibly vibrant, great for group hangouts, and a place where you will certainly stuff your face with overloaded shakes.

(23)   Brewery Hopping in Ravenswood

I could write an entire blog post on the absolute best breweries in Chicago. It is no secret that there are so many craft breweries in the city, but each one has its own charm and fantastic flavor profile. However, if you are only just getting into beer or are visiting Chicago for the weekend, I would suggest trying the Ravenswood Malt Row. This neighborhood is known as Chicago’s craft beer destination, where you can hop between countless small-batch breweries. Start your tour at Dovetail and take it from there!

 

(24)   Feast on Deep Dish Pizza

Nothing says Chicago more than heading indoors to chow down on deep dish pizza. Bonus points if you do this during a blizzard. This pizza, which is really more like a casserole, is incredibly popular in the city and has definitely grown on me over the years of living here. Giordano’s is the most popular option, but I highly recommend checking out Lou Malnati’s for their deep-dish cookie dessert to tie it all together.

(25)   Have Dinner in an Igloo

Finally, if you have a few extra dollars to spend, eat a festive dinner in a winter patio or igloo! We all did plenty of outdoor dining during the Covid pandemic, and I will say that in January, a small space heater will not quell the wind biting your toes (even with four pairs of socks on). Igloos, on the other hand, are heated and incredibly jolly. Some of the best options are Fulton Market and I|O Godfrey. City Winery on the Riverwalk will be offering a new glass enclosure keeping guests warm and dry. They will be closed starting on November 26th, but will open in early 2024 with the renovated indoor patio. Check out this great list by Secret Chicago to see a full list of 20 restaurants!

Frequently Asked Questions

 

Q: Is Chicago worth visiting in the winter?

A: While most people choose to visit Chicago in the summer when you can enjoy the lake, parks, and plethora of alfresco dining options, there is definitely something to be said about visiting Chicago in the winter. Not only are November and December incredibly festive months, but you can get a feel for what life is like in the snow. That being said, if you are not a fan of wind or snow, save your visit to Chicago for the summer.

 

Q: Can you walk in Chicago in the winter?

A: Yes, you can walk in Chicago in the winter as most of the streets are well-cleaned after a big snowfall. The most important thing to note is the wind. The Windy City is well-named for both the political connotations as well as the weather! I am usually a big fan of writing fast-paced and walkable itineraries, but winter is a time where you should scale back on your walking for your own comfort. While a short 10 to 15 minute walk is definitely still an option, I would not suggest exploring the entire city by foot in January.

 

Q: How do you deal with winter in Chicago?

A: Chicago winter is truly defined by two big nemesis: (1) wind and (2) the dark, so to deal with winter in Chicago is to combat both of these things. For the wind, we suggest packing a way bigger jacket than you think you will need. One of the biggest mistakes that tourists make is looking at the weather and forgetting to account for the wind chill. Bundle, bundle, bundle, and bundle some more, with layers and every pair of socks that you own. As for the darkness, this is a tricky one. When the sun sets at 3pm, it can be hard to have the energy to continue with more activities. We suggest getting all your exercise and walking done during the day and leaving the cozier indoor activities for the evening. Winter is a lot easier when you have an evening activity already planned, giving you a reason to stay up past 4pm.

 

We hope this list of 25 Things to Do in Chicago in the Winter has been a helpful way to learn more about the city! Whether you are a tourist or a local, Chicago in the winter doesn’t have to be intimidating. There is something for everyone to beat the gray blues.

 

Out of town and looking to add another U.S. city to your itinerary? Check out our North America travel guides as well as Unlocking Washington DC: An Insider’s Ultimate Bucket List