The Best Things to Do When it’s Winter in Chicago

winter in chicago
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It’s no secret that winter in Chicago can be pretty brutal.  With the wind coming off of the lake, a cold day can feel like a freezing day with just one gust of wind.  But that shouldn’t deter you from making your way to Chicago during the wintertime as there’s so much to see and do inside where you’ll be able to stay warm and still fall in love with the city.  So before you cancel your trip to Chicago in the winter, find out what my favorite winter haunts are and see for yourself what makes the city so magical in the colder months.


The Best Things to Do When it’s Winter in Chicago


Museum Hop Through the City

Chicago has some pretty great museums located throughout the city and museum hopping is the perfect way to spend a cold winter day.  My all time favorite museum in Chicago is The Art Institute of Chicago located downtown across from Millennium Park.  If you visit around Christmas, don’t miss the giant Christmas Tree that is displayed right outside of Millennium Park (this is also where you can see the Chicago bean).

For a complete list of museums in Chicago, check out this post.


Visit Christkindlmarkt

One of my favorite Chicago winter activities happens to fall around Christmas and that’s when Christkindlmarkt opens.  Christkindlmarkt is Chicago’s annual Christmas market since 1996, opening before Thanksgiving and closing around New Years.  The market is modeled after German Christmas markets and it’s a festive way to celebrate the holidays with gluwhein, lights, delicious food, and Christmas cheer.

If you’re visiting Chicago around the holidays, you truly can’t miss it.  For a complete guide to Christkindlmarkt, make sure to check out this post.


 Cozy Up at a Bar

There’s nothing like a cozy bar in the wintertime, drinking red wine, espresso martinis, and escaping the cold while mingling with friends.  Chicago has an incredibly expansive bar scene, but I specifically recommend a *cozy* bar in the winter months.  My favorite bars to visit in Chicago in the winter are Sparrow in the Gold Coast and Lazy Bird at the Hoxton Hotel in the West Loop.


For more bars in Chicago, check out The Best Bars in Chicago


Indulge in Comfort Food

Nothing says winter like some heavy, warm, comfort food.  There’s something about indulging in carbs and heavy dishes in the winter, just like there’s something about indulging in fruits and salads in the summer.  While Chicago has an incredible food scene, there are a couple of restaurants that come to mind when specifically thinking about *comfort food* and *winter time*.

If you’re visiting Chicago in the winter, don’t miss eating at the Italian restaurant Topo Gigio Ristorante (don’t sleep on the conchiglie alla sarda) located in Old Town.  Avec in the West Loop where you definitely can’t miss the crisp rib and sumac hummus.  Gilt Bar located in River North, and Trivoli Tavern located in the West Loop.


For a more comprehensive guide to the restaurants in Chicago, make sure to read The Best Restaurants in Chicago


Have a Spa Day at Kohler Waters Spa

There’s nothing a good spa day can’t fix and luckily Chicago is home to an incredible spa that is perfect for escaping the cold – Kohler Waters Spa.  What I like about Kohler is that while their services are great (massages, facials, etc), there’s also a relaxing area where you can get in the hot tub, sauna, or plunge pool.  It makes for the perfect day if you’re wanting to get out of the cold and stay warm.

Plus if you book a service you’re allowed to hang out at the spa all day for no additional fee.


Drink Tea at The Drake

Located in the heart of Chicago’s Gold Coast, The Drake hotel is most widely famous for hosting Princess Diana when she visited Chicago in 1996.  The second thing that The Drake is most widely famous for is their holiday tea extravaganza.

If I haven’t made it a point yet, Chicago around Christmas time is absolutely magical.  And indulging in tea at The Drake hotel is a can’t miss experience for those who are visiting.  You’ll need to make reservations well ahead of time if you want to spend the day enjoying bubbles, hot tea, Christmas carolers, and tasty pastries.  (Please note, I don’t recommend this experience unless it’s Christmas time.  At other times of the year aside from Christmas it feels overrated and overpriced).


See Chicago from Above at the 360 Degree Observation Deck

While touristy, another great winter activity is to head to the top of the John Hancock building for 360 degree views of Chicago.  Here you’ll be whisked to the 94th-floor, all while learning about the history of Chicago and seeing some of the most famous landmarks from above.

Tickets for adults are $30 with the option to add on a drink or the “tilt”.  I personally don’t think that either add on is worth it and would advice skipping both.


Get Tickets to Broadway

Being the third largest city in America, you best believe that Chicago has a pretty great live show scene.  That’s why one of the best things to do in Chicago in the winter is head indoors to see a Broadway show.

For a complete list of showings in Chicago, check out this website.


Listen to Live Music

There is so much live music to be found around the city, and packing into a full bar, listening to music is the perfect way to stay warm in the wintertime.  While I’m a sucker for a good dueling piano session (Howl at the Moon and Zebra Lounge are my favorite), I’m also a sucker for some good blues or jazz.  For the ultimate live music night I highly recommend heading to Kingston Mines to listen to blues.


Attend a Sporting Event

Chicago has all of the major sports teams – basketball, football, hockey, and baseball!  In the winter heading to a hockey game or a basketball game are ideal if you are craving to get out and experience something different.  To keep up to date on the sporting events (and other events) around Chicago make sure to download the Gametime app.


What are the Winter Months in Chicago?

Unfortunately, the cold can extend long before winter ends (or begins) in Chicago, with November-March generally being classified as the “cold months”.  Out of those months January and December are the coldest months with temperatures averaging 20-30 degrees F.  On top of low temps, you’re also dealing with strong wind gusts and heavy snowfall at times.




While winter in Chicago can feel rough and long at times, there are many ways to entertain yourself.  While Chicago summers are beautiful, I hope that you feel inspired to visit during the colder months to see a different side of Chicago and be met with fewer crowds along the way.


If you’re wanting to visit Chicago in the summer, don’t miss:  10 of the Best Things to Do in Chicago in the Summertime


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Disclosure:  This post may contain affiliate links, meaning I get a commission if you decide to purchase through my link, at no cost to you.


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Kylee is a Neonatal Intensive Care (NICU) nurse passionate about making travel affordable and accessible to nurses. Inspiring nurses to travel both near and far, Kylee began Passports and Preemies in 2017 while volunteering in Skopje, North Macedonia as a way to reach nurses and advocate for the prevention of nurse burnout by traveling. Kylee is the original creator of the “8 Day Vacay” – a vacation geared towards nurses who aim to take advantage of the potentially 8 days off between work weeks with no need to use PTO.

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