Company Logo - Home Link

What to Do in Chicago in Winter


In this post, we explore many of the things to do in Chicago in winter. Yes, Chicago in Winter is cold, but this can still be a great time to visit.

But that does not mean that you can't enjoy our city, feast your eyes upon our architecture, and indulge in our cuisine! 

Experiencing Chicago in the cold is more "the Chicago experience" than the summer.

This is what people in the city live through 9 months out of the year and they are so proud.

Chicago in winter is crisp, cold, often freezing, but still beautiful.

Top 10 Things to Do in Chicago When It's Cold

This is our list of the ten best things to do in Chicago in the winter. While the holiday season is a busy one in December, January and February are off-peak months, making winter the perfect time to visit. 

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

For tips on the most popular Chicago activities, check out the following posts:

For more activities for the winter in Chicago, see our posts covering plenty of great things to do in the following months:

If you still need convincing that winter is a great time to visit Chicago, look at our post when is the best time to visit Chicago. 

1. Take a Sightseeing Tour

The best introduction to Chicago is to take a tour.

Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, and the Riverwalk.

Free Chicago Walking Tours

However, in the winter, we offer a tour of downtown Chicago inside on the Pedway.

2. See a Live Show

Chicago’s theatre scene is a close second to New York’s Broadway (well, we think so!).

The holidays are an amazing time to see a family-friendly show! 

Find all the theatrical performances in Chicago here

3. Take a Bus Tour

It's never a bad time to take a bus tour!

If you're unfamiliar with the city and trying to figure out where everything is located, these hop-on hop-off bus tours are a great way to get acclimated to Chicago.

Best of all, many of the popular winter attractions listed in this post are located near the stops on their route!

4. Go to a Sports Event

Chicago has multiple well-loved professional sports teams, which means that no matter when you come to the city there will most likely be a game happening somewhere. 

The Cubbies might not be playing at Wrigley Field, but the Blackhawks will definitely be on the ice at United Center!

5. Catch a Concert

There is an abundance of great venues where you can find live music in Chicago.

The city has a wealth of local bands and also frequently attracts big-name artists.

If you’re interested in going to a concert, make sure to check and see what’s on at the following venues:

Click here to find all the concerts in the city. No matter the genre you’re into, we’re sure you’ll find it!  

6. Visit our Observation Decks

Chicago has an impressive skyline day or night.

And you can see it all from a birds-eye view and marvel at the architecture from one of the city’s observation decks

The main Observation Decks in Chicago are:

Each is included for free on at least a few of the tourist attraction discount passes.

In addition to these options, there are also plenty of rooftop bars and restaurants with great views of Chicago, including the heated igloos at Godfrey Hotel.

7. Experience the Holiday Festivities

Chicago is full of festive fun from Thanksgiving through New Year’s Day! Check out any of these holiday activities and attractions:

8. Shop for the Holidays

When you are looking for the perfect Chicago holiday gift, you can’t go wrong with these iconic Chicago places and confections:

9. Visit a Museum without the Crowd

Explore the iconic museums and attractions of this city during the winter while staying warm indoors.

Some of the most popular Chicago museums include:

10. Look into a Tourist Discount Pass

Visitors can save up to 50% on retail admission prices with a Chicago tourist pass.

These services provide heavy discounts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various discount passes, which include great year-round activities such as:

If you plan to visit even a few of these attractions, you could easily save quite a few dollars as well as time, since select attractions on these cards have skip-the-line passes.

To find out which city pass will save you the most, read our full post

Ice Skating in Chicago

Nothing is more Midwestern Winter than ice skating. One of our favorite places is the McCormick Tribune Ice Rink in Millennium Park, not too far from the Bean (Cloud Gate).

The Millennium Park Ice Rink opens mid November and remains there until early March. This is a public rink so it's free of charge to use but ice skate rentals are $10.

On Fridays-Sundays, one hour before the rink opens, free ice skating lessons will be offered.

Each Thursday will feature ice sports skills and drills for Noodle Hockey, curling and speed.

Chicago in Winter

Regular Hours for the season are as follows:

  • Monday-Thursday, Noon—8 pm
  • Friday, Noon—10 pm
  • Saturday (Through Jan. 4), 10 am—10 pm
  • Saturday (Beginning Jan. 11), 10 am — 9 pm
  • Sunday, 10 am—9 pm

Special Holiday Hours:

  • Thanksgiving Thursday 10 am—4 pm
  • Black Friday 10 am—10 pm
  • Christmas Eve Dec. 24, 10 am—6 pm
  • Christmas Day Dec. 25, 10 am—4 pm
  • Dec. 26 through Dec. 30, 10 am—10 pm
  • New Year’s Eve Dec. 31, 10 am—8 pm
  • New Year’s Day  Jan. 1, 10 am—10 pm
  • Martin Luther King Jr. Day 10 am—10 pm
  • Lincoln’s Birthday 10 am—10 pm

Indoor Activities

Chicago in Winter

Take advantage of our amazing INDOOR activities like these:

Get museum passes or better yet, get tickets to a show. Chicago has AMAZING theatre.

Try the Goodman Theatre, Steppenwolf Theatre, Broadway in Chicago, Looking Glass Theatre or see some comedy. Laughing keeps you warmer. Check out Second City, I.O. or The Annoyance.

Winter Wonderfest at Navy Pier

Part of the Navy Pier, until early January, this part of Chicago becomes a giant playground right next to Lake Michigan.

It opens daily at 10am and each day the Mayor of Chicago picks a lucky guest to open the Wonderfest, get there early to have your chance at the honor!

Chicago in Winter

Inside the Festival Hall at Navy Pier are rides, games, and more ice skating.

It's free to enter, where you can enjoy the carnival atmosphere and watch the crowds.

But you'll need an activity wristband to take any of the rides.

You can purchase a wristband for $19, which includes ice skating or $15, which does not.

Always the deal seekers here at Free Tours by Foot, if you purchase tickets online or as part of a family pack, you'll get a discount! Certain weekdays are also sold at a better price.

Within the Wonderfest you can find plenty of fun things to see and do including the following:

  • Indoor Ice Skating Rink - rent skates or bring your own
  • Ferris Wheel - get a bird's eye view from 50 feet high
  • Zero Gravity – spin at high speeds on a new, 45-degree-tilted thrill ride
  • Kringle Carousel - hop aboard your favorite animal on this colorful classic
  • Reindeer Express Train Ride - take a ride around the holiday village
  • Snowy Summit Climbing Wall - challenge yourself to reach the rock wall's top
  • Winter Wind Glider - hang onto the soaring glider as you fly 40 feet into the air
  • "Power Wheel" Mini Adventure Track - cruise the course in a mini-Jeep "Hurricane" or mini-Dodge "Police Cruiser"
  • Winter WonderFest Jr. - bounce and tunnel through this section made for the youngest set

There are stages for live entertainment from magicians to jugglers. Each Sunday features a new Latin genre where you can listen and learn the dances and grooves yourself.

At the Craft Corner, in December only, you'll be able to find a FREE Mickey Mouse ornament to decorate and remember your time. You do not need a wristband to make an ornament!

And of course, Santa Claus will be stopping by to visiting the children and listen to their Christmas lists.

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: January 31st, 2023
Back to Top