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What to Do in Chicago in Winter

Updated: May 10, 2024
 By Mel

Believe it or not, our guides offer free walking tours in Chicago all year long, and sometimes when travelers decide to join us during the winter, they'll ask about some of the best things to see and do during this season.

That's why we have put together this post complete with a list of the best recommendations from our tour guides, as well as helpful tips to keep in mind at this time of year.

Yes, the Windy City in the winter is cold, but this can still be a great time to visit.

But that does not mean 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 locals live through 9 months out of the year and they are so proud.

Chicago winters are crisp, cold, windy, and often freezing, but they are also beautiful.


As mentioned above, Chicago is known to be cold in the winter.

Get get a better idea of the temperature and snowfall levels in the city, you can check out the following posts:

It's always a good idea to dress in layers. That way you can feel comfortable when out and about and can remove layers as needed when you're inside.

You'll want to wear a sweater on top of a shirt. Long pants and possibly even thermal leggings will keep you warm.

A thick winter coat, one that is waterproof, and protects you from the wind and moisture is also a good choice.

Hats, gloves (or even better mittens, which allow your fingers to "share the warmth"), and scarves are a must-have.

Thick socks will both cushion your feet on any long walks and prevent you from having to head indoors because your toes are freezing up.

And some solid winter boots—those that are less about fashion and more about traction—will keep your feet dry and prevent you from slipping.

Finally, a pair of sunglasses will serve you well, keeping the glare from the snow from hurting your eyes and blocking the winds.


This is our list of winter activities 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 concession 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. 

Alternatively, you can also check our section covering some of the most popular winter activities among locals and travelers who use our Chicago Travel Tips group on Facebook.

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 theater 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 many other 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!

There are a number of college teams with games in the winter as well.

For even more games, check out this list of sporting events in Chicago.

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 other concerts in the Windy 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.

You can see it all from one of the city’s observation decks. From great views of Lake Michigan to a bird's eye view of the city's architecture, it truly is a great way to take it all in.

The main Observation Decks in Chicago are:

Each is included for free on at least a few of the tourist attraction concession 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!

Here are just some of the winter festivals and holiday events taking place during the winter:

8. Shop for the Holidays

When you are looking for the perfect Chicago holiday gift, you can’t go wrong with some of these iconic Chicago stores.



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 Concession Pass

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

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

Here are a few of the sites you can visit with various concession 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

11. 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 rink opens mid-November and remains there until early March.

There is no cost to enter, but you should secure your ticket for a 90-minute skating session online ahead of time. They release the reservations two weeks ahead of the session dates.

They offer free skating lessons as well, with free skate rentals for the lessons. Reservations must be made.

Skating Session Hours 

2024-25 session schedule is TBD. Last year, it was open from November 17 – March 3

  • Session 1: 11 am -12:30 pm
  • Session 2: 1-2:30 pm
  • Session 3: 3-4:30 pm
  • Session 4: 5-6:30 pm
  • Session 5: 7-8:30 pm
  • Session 6: 9-10:30 pm

Rates for Skate Rentals & Sharpening

Skate sizes start at children’s size 9 through adult 12

  • $16 Monday–Thursday
  • $20 Friday-Sunday & Holidays
  • $10 Skate-aide (2 sizes available) 42 inches & 48 inches
  • $9 Skate Sharpening
  • $2 Locker Rental

*+ $1 credit card processing fee per ticket or transaction

**All sessions have a limited number of free/bring-your-own skate reservations. If the time is not reservable, it is sold out.

12. 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.

13. Light up the Lake at Navy Pier

Navy Pier brings the "largest indoor and outdoor holiday experience" to Chicago with, Light up the Lake.

2024 dates are yet to be released. This holiday event ran from November 24th to December 31st last year.

They've got live music, a heated Ferris Wheel, holiday workshops, axe throwing, ice skating, and more.

There is also a local artisan market where you can look for those last-minute holiday gifts.

For more information and to book your tickets, visit the Navy Pier Light Up the Lake website.

Note that Navy Pier has a Winter Firework Schedule as well, with their award-winning fireworks display taking place on the following dates:

  • Saturday, November 25 at 9PM
  • Saturday, December 2 at 9PM
  • Saturday, December 9 at 9PM
  • Saturday, December 16 at 9PM
  • Saturday, December 23 at 9PM
  • *Sunday, December 31 at Midnight (NYE)

14. Go to a Comedy Show

If you want to head inside where it's warm, a comedy show night might be the ticket.

Some of the most famous comedians in the world come through the city.

The city is also home of the famous comedy theatre, Second City, which sports such alum as John Belushi, Dan Akroyd, John Candy, Tina Fey, Amy Poehler, Chris Farley, Mike Meyers, and many other famous comedians and comedy actors.

Comedy Clubs


15. Go Sledding

While the Midwest is quite flat, there are a few hills in Chicago that will make sledding a lot of fun for kids and adults alike.

Some of the hills are quite long or steep and are probably better for adults and kids who have sledded before.

Others are a bit more gentle and are better for kids and beginning sledders.

Big or Steep Hills

Gentle Hills

Note that some of these sites have lighting so you scan sled (or even snowboard) after dark. Others are near ice rinks. And some are near restaurants you can stop at to warm up afterwards.

To read more about these and other options, visit this website.

16. Head to a Winter Photography Spot

If you want to get some special photos of Chicago in the winter, there are a number of places you can visit.

We've listed just a few of them below.

17. Enjoy Chicago Comfort Foods

Chicago has an endless number of delicious foods that are sure to warm you up on a cold winter's day.

Perhaps its most famous delicacy is the Chicago deep-dish, a pizza around two to three inches tall with a thick crust and loaded with cheese, sauce, and toppings.

Click here for some of the best places to find authentic deep-dish.

Below are a few other foods you might enjoy at the restaurants we've linked to.

Advice From Locals and Travelers

While our tour guides do their best to provide legitimately helpful tips, sometimes it's better to read multiple points of view to get a better sense for what most people think.

As such, we've collected a handful of the best comments from our Chicago Travel Tips group on Facebook to show you the opinions of travelers and locals in the area.

While a lot of people would recommend avoiding Chicago during the winter, some locals and travelers swear by the experience, insisting the snow enhances the experience of the season.

Even then, most of our group members note that it does get very cold during the winter, and that the wind is really what chills you to the bone.

As Andy notes, you should prepare for the weather with very warm clothing.

Beyond Christmas, there are other reasons to visit Chicago during the winter, including the fact that fewer tourists typically means it's easier to get tickets to whatever attraction you might want to see during your trip!

No matter what time of year it is, one of the most popular activities in Chicago is their architectural cruises and tours.

Unfortunately, with the weather getting so cold during the winter, you might think it's not a good time to experience this outing.

However, as Jennifer points out, while the cruises tend to close their service during the winter, they still offer walking tours which actually factor the weather into their journey.

If you do manage to take an architectural cruise during the winter, it'll be nice to know that they have warm inside seating and warm drinks like coffee and hot chocolate!

For even more advice, make sure to check our Chicago Travel Tips group on Facebook and perhaps even ask your own questions about traveling to the windy city during the winter.

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: May 10th, 2024
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