What to Do in Chicago in February (2019)

February in Chicago might be short, but here it is sweet. Below you will find the Top Ten Things to Do in Chicago in February, as well as a list of family-friendly activities, night time activities, and free options so you can enjoy more of Chicago while spending less of your money.


This section covers our top ten list for February. When possible, we’ve noted activities that are free or kid-friendly. For more ideas on popular things to do in Chicago, check out our posts on bus tours and walking tours of the city.

Some of the items listed in this post are included for free with the purchase of a tourist discount pass

Chicago in February1. Ice Skating 

February is the last full month to take advantage of our many outdoor rinks!

There is the McCormick Tribune Ice Rink in Millennium Park and across the bridge in Maggie Daley Park you will find the Skating Ribbon.  

For both rinks, skating is FREE and rentals are $13 on weekdays, $15 on weekends.

2. Rhinoceros Theater Festival

January 18- February 24, 2019
PROP THTR at 3502 North Elston
Admission: $12 in advance, $15 at the door 

This is the longest-running fringe festival in the city, spanning 6 weeks.  Buy a ticket to come and see a variety of artists, featuring new artists and plays, as well as adaptations of some classics such as Shakespeare and Emily Dickinson.

3. Restaurant Week 

January 25 – February 7, 2019

In a city famous for its food, this is a great way to take advantage of the your time in Chicago. Restaurant Week is the perfect opportunity to try some of the best Chicago restaurants.  Hundreds of restaurants participate during Restaurant Week, providing multiple course meals with a prix fixe menus.  Enjoy these dining deals that show off the rich culinary of Chicago.

If nothing else, make sure you try some of the famous Chicago Style Deep Dish Pizza, 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 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.

4. Chicago Theater WeekChicago in February

February 7-17, 2019

During this week, you will be able to find discounted tickets on my than 100 plays throughout the city! For the 7th year, this week celebrates Chicago’s rich theater scene. 

Take advantage of these deals and catch some live entertainment, whether it is musical, new piece, or a classic.

5. Catch a Valentine’s Day Classic Movie

Multiple theaters across the city will be showing some of the classic chick flicks in honor of Valentine’s Day. Favorites such as An Affair to Remember and When Harry Met Sally makes this a perfect date night, or night out in general.

Discover the affordable ticket prices and what is playing here.

4. Cheer on a local team

Both the NHL Chicago Blackhawks and NFL “‘DAAAA Bears” are playing home games this month and each venue is located downtown and easily accessible for travellers. Use this chance to watch a professional sports game and cheer on the home team!

You can get discounted tickets via StubHub for any game that fits your schedule!

5. Polar Adventure Day at Northerly Island

February 23, 2019
Northerly Island Park: 1521 S. Linn White Dr. 

This free event allows you explore nature in this winter wonderland. Come face to face with animals, such as birds of prey, listen to folk music and storytellers, and take advantage of some winter activities such as snowshoeing! Keep warm with some hot chocolate as you enjoy this Chicago tradition.

6. Frost Fest

February 23, 2019

Returning for the second year, the Frost Fest allows guests to warm up in a huge heated tent while sampling 40 craft beers from local breweries. With live music and food trucks, this is becoming a new Chicago tradition.

Tickets include the choice of 15 samples of 3 ounces from 40 craft beers, and a souvenir sampling glass.

7. Randolph St. Market Festival

February 23-24, 2019

Tickets ($10 General admission but kids under 12 are free) 

This year round Market Festival moves indoors during the chillier months, so no need to miss out on this tradition in the month of February.  This market is considered one of the best spots for antiquing and people watching alike. 

In the historic West Loop neighborhood, this European-type market will allow you peruse while discovering treasures such as vintage and antique clothing, jewelry, and furniture.

8. Chinese New Year: Lunar New Year Parade

February 5, 2019

It is the Year of the Dog, and to celebrate the New Year is the annual parade starting at 1:00pm along Wentworth Ave. The parade includes marching bands, colorful floats, and traditional lion dances.

106th Annual Chicago Chinatown Lunar New Year Parade – Celebrating “Year of the Dog” – 4716

from SUPER DEEP Media LLC on Vimeo.

9. Chicago Pizza Party

February 9, 2019

Chicago Deep Dish is the best type of pizza, obviously, but who has the Best Pie in Chi? 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 1-5pm is all ages, kids over 10 years old will require a ticket, kids under 10 are FREE. Session 2 from 6-10pm is a 21+ event. 

10. Explore Underwater Beauty at the Shedd Aquarium

This temporary exhibit features over 100 species of underwater creatures to showcase their beauty, strengths and uniqueness. The exhibit divides the species based on colors, movement, rhythms and shimmer.

Continue to journey throughout Chicago with the Underwater Beauty Murals that have been painted throughout the city. Find the Murals here.

You can get free admission to Shedd Aquarium with a discount tourist pass.

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Night Time Activities: 

Many of our Top Ten activities are perfect for the evening hours, but below are some other suggestions to fill in your evenings during the month of February. Read our post about the Top Ten Things to Do in Chicago at Night for more ideas.  

See Chicago from Above

Watching the sunset over the skyline of Chicago is best done from above. Chicago has two great observation decks, both are open until at least 10pm.

Find out more about the Chicago SkyDeck and the Hancock 360 Observation Deck on our post.

MSI After Dark

February 8, 2019 | 7-10pm

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.

Catch a Comedy Show

With Chicago being the comedy capital of the world, this is a perfect event for some night time entertainment. There are many spots to catch a good laugh.

With popular show options such as Second City and iO, you are such to catch a show to fit your budget and your interest.

You can find discounted tickets to Second City’s 107th Mainstage Revue in February on StubHub.

Grab a Drink at a Speakeasy 

Warm up with some crafty cocktails at one of our numerous hidden bars throughout the city.  Infamous for its 1920’s gangster history, this is a perfect way to experience Chicago.  Some of these bars even provide live entertainment. 

Read all about the best speakeasy bars and how to find them on our guide here.

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Family Friendly Activities: 

Some of our Top Ten are great activities for children, but check out our post about Family Friendly Activities in Chicago for a more complete guide.  Below you will find a couple other options to keep your children entertained this month!

Doze with the Dinos

February 8, 2019

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 its 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.

Take a Walking Tour

All of our tours in Chicago are family friendly. With February weather a little colder than you may be used to, we visit as many indoor locations as we can, include our winter only Pedway Tour to explore the underground and heated tunnels throughout downtown.

Check out our walking tour schedule to make your reservations!

Visit the Chicago Children’s Museum at a Discount

At the Chicago Children’s Museum at Navy Pier, Play Late Thursdays begins on January 3, 2019 in which up to four people can enter the museum for the price of one ticket ($14.95) from 4-8pm.

If Thursdays don’t fit your schedule, you can get free admission with a Chicago Discount Tourist Pass.

This event is every Thursday but on the first Thursday of the month, kids take center stage with programs including:

  • Open mic nights with guest MC’s to run the show
  • Themed dance parties for the whole family
  • Kid-friendly and kid-starring performances


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Free Activities

There are many free activities to take advantage of in Chicago, during every season of the year.  Many of our Top Ten are also free to explore, but below you will find a couple of other free options this month. Check out our comprehensive post about the Top Free Things to Do in Chicago.

Chicago Free Museum Days

There are number of Chicago Museums that offer free admission at certain times, days or for Illinois residents.

Read about the 2019 Free Chicago Museum days here.

Chicago in FebruaryGo 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. 

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

Play at The Beach

January 19, 2019- February 3, 2019

Sounds like a weird suggestion for January, but this is an indoor beach made of plastic balls. Think of it as a giant ball pit with deck chairs, lifeguard chairs, umbrellas and signage that mimic the sensation of a day at the beach.

It is open most days at Navy Pier from 11am-8pm, but get all the details here.

Check out the Chicago Cultural Center

This beautiful and historic building is free and open for the public to explore. They offer their own free tours every Wednesday – Saturday at 1:15pm. Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here.  Check out their calendar of events to see what is going on during your visit.

Go to the Game Room at the Chicago Athletic Association

Inside the historic Chicago Athletic Association building you will find much more than a luxury hotel. On the second floor there is a Game Room with shuffleboard, pool tables, foosball, and bocce. All free to use, find the game master to make a reservation while you enjoy something to sip on.

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