Why Winter is the BEST Time to Visit Chicago

My hometown of Chicago has a reputation for brutal winters.  While this reputation is not necessarily undeserved, winter is still a great time to visit.  I even think winter is the one of the best times to visit Chicago – accommodation costs are lower and attractions are less crowded. (Don’t think you will be alone – even in the middle of winter, there are still plenty of tourists around.)

RELATED – Take a look at A Local’s Guide to 48 hours in Chicago for the best things to do in Chicago year round, what to eat and where to stay.

Prefer to avoid cold temperatures and snow?  No problem. Many of the best things to do in Chicago in the winter can be done indoors so don’t let the weather scare you away. You can easily experience much of what Chicago has to offer while minimizing your time outdoors.  Check out the Chicago Pedway, a huge indoor walkway system that connects several buildings in downtown Chicago.  To minimize walking outside, use public transportation, taxis, Lyft and Uber to get around Chicago. (Use my Uber referral code to earn $2 off your first 3 rides.)

Top things to do in Chicago in the winter include:

1) Check out Chicago’s museums, skyscrapers and other indoor tourist attractions.  Chicago has many great museums and other indoor attractions including the Field Museum, Museum of Science and Industry, Shedd Aquarium and Adler Planetarium. Art lovers can visit the Art Institute of Chicago and the Museum of Contemporary Art.  Other Chicago tourist attractions not to be missed include the views from the John Hancock Center or the Skydeck at Willis Tower (formerly known as the Sears Tower).

Tip: To save money on entrance fees and skip long lines, I recommend purchasing a tourist pass.  A tourist pass will save you money on entrance fees for museums and other attractions and let you skip the lines at several attractions (the Skydeck at Willis Tower often has 2 hour long lines!).  Some museums offer free admission on the first weekend of every month to Bank of America credit or debit cardholders under the Bank of America Museums on Us program.

2) Attend a play, show or sporting event. Chicago has one of the best theater scenes in the world, including several Broadway productions. Fans of improvisational comedy can check out Second City- the training ground of many notable alumni who went on to star on Saturday Night Live. If you enjoy sports, get tickets to a Chicago Blackhawks hockey game and see the reigning Stanley Cup champions in action.

3) Eat, eat and eat some more. Chicago is traditionally known for deep dish pizza and Chicago-style hot dogs.  Add in a number of great restaurants and you have a foodie paradise.  In fact, there are so many great restaurants in Chicago the choices seem endless.  Some recommendations for first timers include:
– Sampling a deep dish pizza. Lou Malnati’s Pizzeria in River North is a crowd favorite.
– Ordering a Chicago-style hot dog (remember, no ketchup allowed). Portillos is a great choice with a convenient drive thru window.
– Foodies and fans of Top Chef.  Top recommendation is Girl & the Goat and sister restaurant Little Goat (Executive Chef is “Top Chef” winner Stephanie Izard).

Another great thing about visiting Chicago in the winter is Chicago Restaurant Week, where participating restaurants offer special prix fixe menus. This is a great opportunity to dine at some of Chicago’s best restaurants while saving on dining costs. Chicago Restaurant Week is held every winter (dates in 2020 are January 24 – February 9, 2020).

These are some of the best things to do in Chicago during winter.  If you end up loving Chicago (most people do), you can always return in warmer weather for Chicago tourist attractions you can enjoy year round.
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Why Winter is the BEST time to visit Chicago Things to do in Chicago in the Winter



  1. This post is too timely. I’ll be visiting Chicago for the first time next weekend (12-15) and I’ve had to answer ‘why not’ everytime someone has asked me why! From what I saw, like you said, there are so many great things to do indoors in Chicago that the weather doesn’t matter. Thank you for making me feel better about booking in mid-winter!!

  2. This is awesome! Normally, people would be deterred to travel anywhere during winter but seeing how many things you can do in Chicago – I think it’s safe to say that it’s an all-year round destination. 🙂

  3. I was so worried moving to Chicago just before winter was going to be a real downer, So I am so pleased to see that there are still things to do here. Thanks for the post

  4. I went to Chicago last month and I am craving Shack Shake and a red velvet fudge shake from the Willis Tower… Like RIGHT NOW!!!

  5. A great article! As a native Chicagoan, it’s refreshing to look at and appreciate our fantastic city through the eyes of a tourist to put into perspective all the fantastic things to see and do we take for granted! I love, love, love this stunning city. It is my heart, and winter is absolutely our time to shine!

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