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What to Do in Chicago in February

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This post covers the best things to do in Chicago in February, including, free, family-friendly, as well as nighttime events and activities, all updated for 2020.



CHICAGO HOTEL DEALS ON TRIPADVISOR – If you haven’t already booked your accommodations.


February in Chicago is a great time to visit because it is a slow season for tourism which means you won’t have to wait in lines or stand in crowds! 

Check out the suggestions below for a variety of activities, including sports, theatre, music, and lots of indoor activities to stay warm!

For some of the more popular things to do in Chicago, read the following posts:

1) Go to a Sporting Event

Chicago loves sports so if you are visiting and want to feel like a local- be sure to catch a game.

In February, you can head west to the United Center for a Basketball or Hockey game. 



For a list of all sporting events happening this month, check this list.



Find all the events here.

2) Go to a Concert

February is the perfect month to enjoy an indoor concert. There are many intimate music venues in Chicago to explore, especially downtown and in Lincoln Park.

Check out our Chicago Blues post for a few other suggestions. 



Here are just a few of the larger-scale concerts happening in February of 2020. 

Find all the concerts in Chicago here.

3) Take a Sightseeing Tour

Be sure to bundle up with many, many layers while roaming outside in Chicago during February. 

Cold doesn’t stop our amazing history-loving storytelling guides though! We offer pay-what-you-like walking tours nearly every day of the week in the Windy City.  



Try our seasonal Chicago Pedway tour to experience the indoor paths that run under the city or the seasonal Winter Loop Tour for a winterized Loop experience. 

Want to learn about our amazing Architecture? Check out the Winter Architecture Tour.

If you’d prefer the heating on a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.

4) Go to the Theater

Chicago is home to many many regional theatres, small black box spaces, and Broadway Tour houses. There is something for everyone!  

To see a full calendar of all shows or to buy tickets for shows, click here.



Here are just a few of the many shows happening in February 2020:

  • Blue Man Group at the Briar Street Theatre (runs continuously) is a great show for everyone in the family- even people were are not native English speakers!  
  • Once on this Island at the Cadillac Palace from January 21 - February 2. 
  • Roe at Goodman Theatre (January 18-February 23). The story of Roe v. Wade.
  • Men Are From Mars, Women Are From Venus at the Broadway Playhouse (February 11-23) is a hilarious comedy! 
  • Summer: Donna Summer Musical at the Nederlander (February 12-23) is a great musical.
  • Bug at Steppenwolf Theatre (January 23-March 8). A tale of love and government conspiracy.

Find all the theatrical productions in Chicago this month here.

Pro-tip: February 13-23 is Chicago Theatre Week!  Be sure to look for discounted tickets! Also, Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.

5) See More for Less with a Chicago City Pass

Many of Chicago’s biggest attractions have entry fees.

While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.



They can also save you time with skip-the-ticket-line privileges.

Each Chicago tourist discount pass includes a variety of fun activities and attractions.

Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.

6) Ice Skating in Downtown Chicago

Ice Skating is a great way to spend the day or evening hours, especially with numerous rinks around the city.

There is the McCormick Tribune Ice Rink in Millennium Park. Right underneath Cloud Gate and on the edge of the downtown area makes this a perfect spot, and you can warm up with some hot chocolate served right next to the rink. 



Across the bridge in Maggie Daley Park, you will find the Skating Ribbon. Surrounding the rock wall and with the skyline in the background, this is a “skating through the alpines” experience. 

For both rinks, skating is free and rentals are $12 on weekdays, $14 on weekends.

7) Chicago Restaurant Week

Traveling through your taste buds is always a fun thing to do when it is cold out! 

Chicago Restaurant Week (January 24 – February 9, 2020) is the perfect opportunity to try some of the best Chicago restaurants.

Hundreds of restaurants participate during Restaurant Week, providing multiple course meals with fixed-price menus.  



If nothing else, make sure you try some of the famous Chicago Style Deep Dish Pizza or enjoy a romantic fondue dinner.

But if you’re still hungry, sample your way with these self-guided food tours of Chicago neighborhoods.

On a budget? You can still get a taste of Chicago with some of the best cheap eats in the city. Or if you want to get a background with your brunch, take one of the best Chicago food tours.

And when you’ve finished sampling, relax with something from a local coffee shop.

8) Celebrate Valentine’s Day

There are a few American Holidays in February including Groundhog’s Day on February 2nd, Abraham Lincoln’s birthday on February 12th, and President’s Day on February 17 (bank holiday).



The one that Chicago really celebrates is Valentine’s Day on February 14th! You can find live music, romantic walks, and special menus at local restaurants.

We have more details and suggestions on how to spend your day on our blog.

9) Chicago Pizza Party

On February 9, 2020, join the Chicago Pizza Party!

Chicago Deep Dish is a hearty delicious pizza that can be compared to none, but who has the Best Pie in Chicagp?

This all-day party brings together top pizza shops in the city to earn the right to claim they are the best. 



Taking place on #NationalPizzaDay you can indulge in pizza, but also games, DJs, and drinks. Tickets are $20.

Session 1 from 1:00 pm - 5:00 pm is all ages, kids over 10 years old will require a ticket, kids under 10 are FREE. Session 2 from 6:00 pm - 10:00 pm is a 21+ event. 

10) Go to C2E2 - Chicago Comic and Entertainment Expo

From February 28 - March 1, 2020, a huge event for comic lovers and gamers is in town. It is located at the Mccormick Place near downtown Chicago.



There will be panel discussions, activities, shopping, and plenty of cosplay!

The vendors in attendance will be filling the main floor to keep you occupied between events with some of the bigger names in comics and sci-fi media. 

If you are interested, be sure to get your tickets soon!


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Chicago offers many free activities throughout the year. Some of the events mentioned above are free too! Here are a few suggestions during February 2020.



For more ideas, check out our post about the top free things to do in Chicago.

Celebrate Groundhog’s Day

On February 2nd there is a little holiday based on a Pennsylvania Dutch superstition called Groundhog’s Day.

The tradition is that a groundhog is brought out and if they are scared of their shadow and retreat back - that predicates that winter will continue for 6 more weeks. 

Later, a popular Bill Murry movie was filmed in Woodstock, IL, based on Groundhog’s DayEver since, Woodstock, IL has a great event. 

While Woodstock isn’t really close to Chicago, if you are nearby, it could be worth a visit!

Maxwell Street Market

Bundle up to enjoy the international flare at this market on Sunday mornings between 7:00 am – 3:00 pm which has been a Chicago tradition for over 100 years. 

Take in the bargains and culture at this year-round market. The market has free admission. For more details, click here. 

Attend a Free or Donation Museum

There are many wonderful museums in the Windy City that are actually free!  

The Jane Addams Hull House is an incredible museum that is located in one of the original Hull House homes. 

The National Museum of Mexican Art is a donation-based museum for art lovers.

Another option is to go into the bottom of the Watertower for a small but mighty free art museum! If you are joining us on our Pay-What-You-Like Magnificent Mile walking tour- you will enter this museum with your tour guide.

During the winter months, locals will find that many of the museums offer free days to Illinois residents, teachers, veterans, etc.

Art on the Mart

Even with the cold, the Art on the Mart will persist!

Head the Riverwalk at sunset to see an amazing art projection on the Merchandise Mart Building (a building so large, it has its own zip code!) 

The Bridgeport Art Center

Located in the Bridgeport building which is a creative home for local artists and designers, there is an outdoor sculpture garden and three curated art galleries. 

On the 3rd Friday of each month between 7:00 pm - 10:00 pm, people are invited to see the painters, sculptors, photographers work.

Check out the Chicago Cultural Center

A great place to warm up while appreciating architecture is the Cultural Center. This beautiful and historic building is free and open for the public to explore. 

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here.

This is also a great place for children’s programming. They offer their own free tours every Wednesday – Saturday at 1:15 pm

Check out their calendar of events to see what is going on during your visit.

Go to the Lincoln Park Zoo and Conservatory

The Lincoln Park Zoo and Conservatory are both free and open 365 days out of the year! Head up to this beautiful park to visit some of the animals, especially the polar bears!

If it starts to get a little chilly you can stop into the Conservatory to warm up and see the beautiful plant life there.

Explore Navy Pier

It is free to visit Navy Pier and there are plenty of things to enjoy without spending a dime. You can take our free self-guided tour to really take in the sites.  

If you want to beat the chill, head to the Crystal Gardens to appreciate an indoor tropical garden with jumping fountains! If you don’t mind the blustering wind, head to the end of the pier for an amazing view of Chicago.

For more ideas, check out our post about the Top Free Things to Do in Chicago.


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Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event, going to the theater, or attending a concert.



Below are some more ideas. Be sure to read our post about the top things to do in Chicago at night for even more suggestions.

Laugh at a Comedy or Sketch Show

Chicago is known for its food and its comedy! Some of the best comedians came out of the Windy City. Amy Pohler, Tina Fey, Chris Farley- to name a few.  

In the cold nights of February, a good laugh will be sure to warm you up. Check out Second City for sketch comedy, stand up and improv. 

Another local favorite is i.O. which is improv and sketch. Head to the Laugh Factory for stand-up. There are shows for everyone’s budget.  

Check out a Drag Show

Head to the South Loop to attend Lips Drag show which has been around for 25 years.

It has performances on Wednesdays - Sundays; including a Sunday brunch! 

MSI After Dark

The MSI After Hours is an Adults Only experience to explore the museum after the day time guests have left.

Each After Hours event lets you enjoy cocktails, beer, snacks and new programs each month.

Adler After Dark

On the third Thursday of each month, Adler Planetarium opens up for a fun night-time event for adults. 

There will be drinks, music, and entertainment while enjoying looking at the stars. Escape the cold and enjoy this monthly event.

Go Out for a Cocktail

Keep your layers on and head out for a cocktail!  Chicago is known for locally brewed craft beers and a unique liquor called Malort. Taking a shot of Malort will definitely warm you up!   

Another fun option is to check out one of our famous speakeasies – fitting for the mobster history of the Windy City. The Office is a unique cocktail experience that is indulgent with completely personalized beverages.

Mixing music with cocktails always fun! Check out Kingston Mines to enjoy the blues or Davenport’s Piano bar for a unique experience.  

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.


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Below you will find several great options to keep your children entertained this month, including parks, museums, and theater!



Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

Northerly Island Adventure 

Head to Northerly Island to explore with the kids. See birds of prey and wolves, make nature-inspired winter crafts, walk on snowshoes and drink cocoa at Polar Adventure Days

This event is free to attend.

Orchid Show at the Botanical Gardens

From February 8-March 22, you can visit the Chicago Botanical Garden to see the Orchid Show. There will be over 10,000 orchids in bloom and many lovely tropical plants.

Doze with Dinos

Families with kids ages 6 to 12 can pack their sleeping bags and spend the night at the Field Museum!

You can stay up late with the scientists and tour the exhibits with your flashlight. When it's time for lights out, you’ll have a spot in the Genius Hall of Dinosaurs.

Find out more about the Field Museum on our post and if you want to stay the night, get tickets soon here.

Dates: January 17 & 24, February 7 & 28, March 7 & 27

Family Science Day

On February 8th, Fermi lab out in Batavia is hosting a family day! There will be tours, hands-on exhibits, and lessons on physics for kiddos third grade and up.

Juice Box Concerts at the Cultural Center

Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am-11:45 am for an engaging musical event!  

While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6. See their website for more.

Go to a Family-Friendly Improv Show

ComedySportz is known for being family-friendly!  It is a game inspired improv show- similar to Who’s Line is it Anyway? If anyone on the team uses a curse word- they actually lose points!

This means that this show is really made for all ages.

Juice Box Concerts at the Cultural Center

Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am - 11:45 am for an engaging musical event!  

While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6.

See their website for more.

Go to a Museum

Chicago has a lot of museums that are very interactive and ideal for kids. Some of our favorites include:

Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.


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About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 12th, 2021
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