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What to Do in Chicago in February

Updated: November 25, 2023
 By Mel

This post covers the best things to do in Chicago in February.

We include free, family-friendly, as well as nighttime events and activities, all updated for 2024.

If you haven’t already booked your accommodations, check out a list of CHICAGO HOTEL DEALS ON TRIPADVISOR.


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, theater, 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

While February is cold outside, cheering on your teams inside will keep you and your friends and family warm.

A number of teams will be playing home games this time of year



Click here to see more sports events taking place in Chicago in February. 

2. Go to a Concert

If you are a music lover or a fan, be sure to check out a concert while in Chicago.

There are many venues in the Chicago area, from giant spaces to intimate bars.


Opera/Classical Concerts

Music Festivals

Click here to see more Chicago-area concerts happening in February.

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

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!  


Special Events


Check here for even more events in the Chicago area in February

Pro-tip: February 8th - 18th 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. Visit the Chicago Auto Show

The nation's largest auto show was first staged in 1901! It returns to Chicago again in 2024 from February 10th through 19th.

Over 1,000 domestic and imported cars and trucks, as well as experimental and concept cars, will be on display.

You'll also find many auto exhibits, antique and collector cars, and more.

All of this takes place at McCormick Place. Tickets are inexpensive and can be purchased here.

6. Go Ice Skating

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. 

Gallagher Way, close to Wrigley Field, has an ice rink along with a Winterland Festival and Christkindlmarket Wrigleyville.

There's also a Midway Plaisance Park ice rink, one at Mt. Greenwood Park, and one at Warren Park.

Finally, if you want to skate surrounded by skyscrapers, try The Peninsula Sky Rink.

7. Enjoy a Stand-Up Comedy Show

If you're in need of a good laugh, some of the most famous comedians in the world will be performing stand-up in the Chicago area this February.

Each of these performances is scheduled to take place either in Chicago or within around 30 minutes of the downtown area.

Comedy Shows

Comedy Clubs


Check here for a even more comedy shows taking place in Chicago in February.

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 20th (a 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.

You might try making reservations at one of Chicago's most romantic restaurants. Many restaurants will have Valentine's Day specials.

You can also visit Love Bites: A Valentine's Haunted House in Schiller Park.

Just before and after Valentine's Day, take your loved one to the Chicago Botanic Garden to admire the Orchid Show of Wonders.

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

9. Go to a Ballet or Symphony

There will be several opportunities to see a live ballet or symphony perform in Chicago this month.

The Joffrey Ballet will be performing Studies in Blue from February 15th - 25th.

The Chicago Symphony will also have a handful of performances this month, including Tchaikovsky and Shostakovich on February 23rd, 24th, and 27th.

For something a bit different, you might try a Candlelight Concert.

These take place in a number of styles, including classical. There will be tributes to Adele, Taylor Swift, and ABBA in February.

10. 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.

If you know already which discount pass works best for you, it can be purchased here: All Inclusive - Chicago Go City | Explorer - Chicago Go City | Chicago CityPass


Chicago offers many free activities throughout the year. Some of the events mentioned above are free too!

Here are a few suggestions for February 2024.

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 Day. Ever 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!

Attend a Free or Donation Museum

There are many wonderful museums in Chicago 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.

The Block Museum of Art offers free entrance to its cinema screenings and access to its collection of sculptural works for free as well.

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

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, and 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 Thursday and Friday 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.  

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


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.

Check out a Drag Show

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

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

Adler After Dark

Every Wednesday, Adler Planetarium is open from 4:00 pm -10:00 pm.

"You’ll find hands-on, minds-on activities, experiences, and shows about the universe that will blow your mind!"

More information can be found on their website.

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 is 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.


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.

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 here.

Dates: February 2nd-3rd, 2024.

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.

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.


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: November 25th, 2023
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