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50 fun things to do this winter in Chicago!

Snowing in Chicago

Chicago is a wonderful city with endless opportunities for entertainment and recreation. Chicago’s world class cultural attractions and amazing architecture are the standouts of this great city. Unfortunately, many tourists never consider Chicago to be a winter vacation destination due to the snow and cold temperatures. Luckily, many of the best attractions are located indoors, and the festive outdoor attractions are worth braving the cold, bundled up of course!

Do you think of Chicago as a summer only destination? You are missing out big time if a winter vacation has never crossed your mind! In Chicago, there is plenty of fun to be had year-round! As a long time former resident, I have come up with some of my favorite things to do over the winter months. In fact, I actually prefer the winter months due to the quieter atmosphere and abundance of dreary, snowy days.

Whether you are a local looking for new interesting activities this winter, or a tourist planning a winter getaway, you are bound to find a few ideas for winter fun on my list. What are your favorite Chicago winter activities? Feel free to give your own suggestions in the comments below!

1. Visit The Art Institute
Art Institute of Chicago at Christmas

The Art Institute of Chicago is one of the world’s best art museums. Visiting at any time of the year is a once in a life experience, however, visiting during the holiday season is even more spectacular! The beautiful lions out front wear festive wreaths during the holiday season! On a budget? Visit Thursday nights for free admission (5-8pm for Illinois residents).

Address: 111 S. Michigan Ave. Chicago, IL 60603

2. Go ice skating in Millennium Park

Millennium Park Ice rink

Ice skating at the McCormick Tribune Rink at Millennium Park is one of my favorite winter past times in the city. There is nothing better then heading downtown on a brisk, snowy winter day, and taking in the spectacular Chicago architecture while skating along to holiday music. Great prices for a city rink! One of the few city ice rinks you will find offering free admission (your only cost will be skate rentals, unless you own a pair).

Address: 55 N. Michigan Ave. Chicago, IL 60601

3. Take a stroll down Michigan Avenue

Magnificent Mile in Chicago

Michigan Avenue: home to the world famous Magnificent Mile shopping district. How could you not want to spend your holiday season shopping along this beautiful street, complete with prestigious shops, fun restaurants, and scenic holiday decor?! Definitely plan for a stop at Water Tower Place, an upscale 8 floor shopping center located at 835 N. Michigan Ave.

In addition, be sure to check out the Magnificent Mile Holiday Lights Festival, which takes place each November. This popular, festive event include many activities: a parade, concerts, and a fireworks show over the Chicago River are a few of the highlights.

Address: N. Michigan Ave. Chicago, IL 60610

4. Experience an authentic Italian dinner at The Rosebud

The Rosebud - Chicago

A winter visit to Chicago would not be complete without a delicious Italian dinner at my favorite restaurant, The Rosebud. This upscale restaurant located in Chicago’s Little Italy neighborhood features a spectacular menu, a romantic setting, and impeccable service. This charming restaurant was Frank Sinatra’s favorite: imagine that!

Address: 1500 W. Taylor St. Chicago, IL 60607

5. Be amazed at Lincoln Park ZooLights Festival

Lincoln Park Zoo Lights Chicago

Take advantage of this festive display of over 2 million lights, held annually each year at Chicago’s beautiful Lincoln Park Zoo. This free event features multiple themed activities including ice carving demonstrations, carolers, and a synchronized music and light show. The ice carvings are absolutely fantastic; these artists really have a unique talent. Zoo Lights is the perfect holiday event: strolling around with a hot chocolate while taking in the wonder of all the dazzling lights makes a perfect winter date night destination.

Address: 2001 N. Clark St. Chicago, IL 60614

6. Visit the spectacular dinosaur & mummy exhibits at The Field Museum

The Field Museum Chicago

Most of you have probably heard about Chicago’s famous Field Museum. Reading about this museum is much different than actually seeing the incredible dinosaur fossils in person. Home to “Sue,” the most complete fossil, The Field Museum is tops on my list of must-dos in the city. Take a break from shopping in the cold, brisk Chicago air to tour this incredible museum! If you plan on visiting The Field & the Shedd, along with other Chicago museums and attractions, you should definitely look into a combined attraction discount from CityPass.

Address: 1400 S. Lakeshore Drive Chicago, IL 60605


  1. Your Welcome. Fortunately, there are tons of things to do in Chicago year-round, even during the winter season that so many despise so much. It’s actually the best time of the year in Chicago in my opinion 🙂

    • Whitney
    • June 17, 2018  at  6:00 PM

    I have lived here for about 6 months and have been so busy with my new job that I haven’t taken time to check out the things that make this city so magical, but with family coming soon its time. Thanks for the information!

  2. Thanks!

  3. Wonderful article. Truly, ice skating in Millennium Park is really very amazing thing to do. I love to read this post, It reminds me my back days.

  4. Great blog. Traveling is the best option to take away your headache from busy schedule. If you want to travel from Winnipeg To Chicago through driving then contact us via!

    • jack
    • January 23, 2018  at  6:57 AM

    Nice Post!! Try Winter park things to do in colorado

  5. I have been in Chicago but not in winter. It really worth visiting in summer too. I will surely be going to visit Chicago again in few months.

    Have a great time – there is plenty to do year-round. Be sure to check out my summer list too!

  6. I have been in Chicago but not in winter. It really worth visiting in summer too. I will surely be going to visit Chicago again in few months.

  7. Your welcome! There are plenty of fun things to do year-round in Chicago. As for dog friendly activities, many restaurants and shops are pet friendly. Bring Fido basically lists all the dog friendly places around the city. And Navy Pier is super dog friendly – most of the restaurants and shops allow dogs. And of course, dog parks are always fun anytime of year. And be sure to check out Seadog Cruises in the summer – amazing views and you can bring your dog with you! Hope these links help!

    • mila
    • September 15, 2017  at  2:16 PM

    thanks for this! im relocating to chicago (yes on purpose haha) and it will more than likely be in november and my first time in a chicago winter so im looking for positive articles for what to do! i’ve lived on the east coast before so i know about snowy winters but this will be my first one living and working in the city/urban environment so this really helps! any ideas what to do with your dog in winter in chicago? 🙂

  8. Thanks!

    • Rooy
    • June 22, 2017  at  6:22 AM

    Chicago is my hometown i alway visit there at vocation thank for this article .it is amazing article.

  9. I do have a summer version available – check out 25 fun things to do this summer in Chicago

  10. Thanks! Have a great trip!

    • suraj
    • January 18, 2017  at  7:06 AM

    This is a great list! I’m visiting Chicago for the first time in October 2017 so this is getting me so very excited !!

    thank you for sharing your experience with us.

  11. Your welcome! Hope you have a great trip! 🙂

    • CCR
    • January 12, 2017  at  5:20 PM

    Thank you for this article! I’m getting ready to go to Chicago and your list has been extremely useful!

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    • Matt
    • February 19, 2015  at  9:34 PM

    You forgot to include skydiving in Chicago during winter!

    • Zach
    • February 7, 2015  at  11:57 PM

    Beware some of the restaurants on this list are chains. Venture out to neighborhoods away from mag mile as a resident of the city I rarely go to that neighborhood or the loop.

  13. It’s one of the best holiday events in the Chicagoland area. I highly recommend checking it out! 🙂

    • Rob
    • November 20, 2014  at  5:53 PM

    I cant believe I haven’t been to the Lincoln park zoo lights. Looks like a great activity to take the family too.

    • JoguruTravel
    • April 8, 2013  at  5:21 AM

    Recently visited my cousin in Chicago and I had just 3 days to complete my work and enjoy. So we decided to spare a full day to roam around the city. We covered most of the things to do in Chicago mentioned in the above post.

  14. Yes – The Brookfield Zoo Lights are always amazing! I also like the fact that they open the indoor exhibits (Tropic World, etc so you can take a break from the cold). On top of that, they have really cool ice carvings each night, a laser light snow, holiday choir performances, and holiday music! This event is definitely always on my Holiday event list when I am in the area!

    • Jessi
    • March 8, 2013  at  4:46 PM

    I visit Chicago semi-regularly (I used to live only a few hours away, but the Brookfield Zoo lights are one that I never managed to make happen. It’s only in December, which is usually full of holiday plans for me instead of day trips away. Is it really as awesome as I have heard?

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