Things to do in Chicago in Winter: Why You Should Visit When It’s Cold

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You might be asking yourself what is there to do in Chicago during the winter? Why would anyone in their right mind want to visit Chicago during the icy cold?

Winters in Chicago can be frigid. But it doesn’t mean you can’t have fun.  It just means you gotta dress warmly.  Wear a warm coat, dress in layers, and wear a pair of fashionable but weatherproof boots (the salt mixture used to melt snow is murder on boots – so don’t wear your Uggs). Don’t forget to wear a hat and gloves!

That is the key to surviving the arctic cold of Chicago without encountering frostbite.

There are plenty of cool (get it winter…cool) things to do in Chicago. The month of December is full of winter wonderland fun.  Things taper off at the beginning of the year, but there are three huge events in January and February you don’t want to miss!

In this article, I discuss the best things to do in Chicago in the winter.



Things to do in Chicago in December

Check out the 36th Annual Christmas Sing-A-Long and Double Feature at the Music Box Theater – Sing-a-long with other Christmas carolers and watch a double feature (White Christmas and It’s a Wonderful Life) as part of Music Box Theater annual Christmas celebration. Dates: December 12th – December 24th, 2019.  For more information on the Music Box Theater Christmas Sing-A-Long, click here.

The Music Box Theater is located in the Chicago neighborhood of Lakeview at 3733 North Southport.

Christkinkl Market – is an open-air Christmas festival held every year at Daley Plaza (50 West Washington Street) in downtown Chicago.  Inspired by the German Christmas Markets in Europe, enjoy a unique shopping experience by exploring the many vendors, international food choices, and holiday performances. Dates: November 15- December 24, 2019.  For more information, click here.

Macy’s Christmas Windows –  Beginning in early November – Macy’s at 111 North State Street showcase their holiday window exhibits.  Be sure to check out the 45 foot giant Christmas tree inside of the Walnut Room.  Or even better book reservations at the Walnut Room for a bite to eat after Christmas shopping.  Dates: November 1 through the end of the year.

Magnificent Mile Light Festival and Parade – the beginning of the shopping season is ushered in with a bit of fanfare…the Magnificent Mile Light Festival and Parade!

Although this is actually in November, I wanted to mention it here.  It is a big event that droves of people come to Chicago every year to partake in.

It is 2-days of festive activities topped off by a parade down the Magnificent Mile (North Michigan Ave).  Dates: November 22-23, 2019.  For more information on events surrounding the Light Festival and Parade, click here.

Christmas around the World at the Museum of Science and Industry – If you’re into Christmas Trees, you don’t want to miss Christmas around the World at the Museum of Science and Industry.  Since 1942, the Museum of Science and Industry (5700 South Lake Shore Drive – Hyde Park Neighborhood) has showcased the Christmas all-around-the-world Tree exhibit.  The exhibit also includes holiday live performances on the weekend.   Dates: November 14 through January 5, 2020.  For more information, click here.

Things to do in Chicago in January

Fresh Bites Bash – the kick-off event for Restaurant Week is held at the Field Museum (1400 South Lake Shore Drive).  Here’s your chance to sample delicious bites (for a fee of course) from 60 different well-known Chicago chefs whose restaurants are part of Restaurant Week.  A great way to experience all of the participants in one sitting.  Tickets sales and date: TBD.

Chicago Restaurant Week – If you’re a foodie, you don’t want to miss this week of food, food, and FOOD!  Restaurant Week (it’s 17 days) is a culinary look at the fantastic food scene in Chicago.  Each participating restaurant will offer a multi-course meal, either brunch/lunch for $24 or dinner, which could be either $36 or $48. Dates: January 24th through February 9th, 2020.   Reservations for participating restaurants will begin on December 10th.  For more information, click here.


Things to do in Chicago in February

Chicago Theater Week – is a great time to score your cheap tickets to great productions in theaters playing all over the city of Chicago.  From musicals to opera – you can experience the best of the best for the do-able price of $30 or less.  Dates: February 13th through February 23rd, 2020.  For more information, click here.

Festival of Films from Iran –  A celebration of Persian culture captured through the lens of various filmmakers.  Held at Gene Siskel Film Center (164 North State Street).  Dates: TBD – check back later.


Why you should visit Chicago during the winter

December through February is considered low season for Chicago due to its harsh winters.  Hotel rates and airfare are usually cheaper during this season.

Where to stay in Chicago Downtown

I recommend staying at Hampton Inn Majestic (22 West Monroe) – The Hampton Inn Majestic is located in Chicago’s Theater District.  It is the perfect location if you’re flying in for Theater week in February. The Hampton Inn Majestic is right next door to the CIBC Theater and a block away from shopping on State Street.  Rooms range in size from 285 square feet to 350 square feet.  Click here to go straight to to book your room.

And let’s not forget Airbnb.  Some hosts do offer better rates in the wintertime.  To research Airbnb rates for the winter, click here.

To read more about where to stay, read my article “Where to Stay In Chicago.”


How to get to Chicago


Two airports service the Chicagoland area; O’hare Airport (ORD) and Midway Airport (MDW).  You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transit, the Chicago ‘L’ trains.

Traffic from the airports is horrible unless you fly in very early or late (after 7 PM).  Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L.’  During rush hour (6 AM- 10 AM and 2 PM – 6:30-7 PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).


Union Station (225 South Canal)Click the link for more information on Amtrak.


Greyhound Bus Station (630 West Harrison St) or Megabus (Van Buren St between South Canal and Clinton St)


Three expressways run through the Chicagoland area: Interstate 90/94, Interstate 55, Interstate 290.


Staying Safe in Chicago

Yes, parts of Chicago can be dangerous.  But don’t most major cities (both U.S. and abroad) have elements that are considered not safe? With a little street-savvy and awareness of how you’re presenting yourself, you will be fine.

  • Just like any city that you visit, always be aware of your environment.
  • Try not to appear touristy.
  •  If you’re like me and love carrying huge-ass purses, make sure the bag has a shoulder strap that you can wear across your body.
  • Never leave your purse on the back of your chair.  Especially if you are enjoying a meal at one of Chicago’s many sidewalk cafes/restaurants.
  • Do not take shortcuts through alleys.  No matter how tempting.
  • When going out at night, stick to well-lit sidewalks, main streets, and parks.  The lakefront is gorgeous at night.  Full of good people with neighborly and friendly mid-western values.  Join them and enjoy the amazingly beautiful city that is Chicago.  I never get tired of the welcoming energy of my city.
  • Enjoy yourself.

The City of Chicago Police heavily patrols the downtown area and all neighborhoods.  University Police also patrol some communities such as Hyde Park and parts of Lincoln Park.  So like I said…feel free to enjoy yourself but do it safely.


There’s a lot going on in the Windy City. Read more about Chicago by clicking on the following articles:


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