Visiting Chicago in the middle of winter? Many of my friends may have thought I was crazy to plan Chicago as a vacation destination in December. But if you can brave the cold, Chicago is a fun, romantic spot for a weekend away!
My now husband and I chose Chicago as our winter vacation after doing Christmas in NYC a few years back. We wanted another city that could give us what NYC has offered us: shows, sites, and delicious food! We found a good flight deal (winter is the off season) and headed off to Chicago for the holiday!
On day one, we warmed up at Wildberry Pancakes and Café before heading out into the winter weather. We tried one of their holiday flavored mochas and specialty benedicts and left happy and ready for the day.
Just across the street is Millennium Park. If you enjoy ice skating, McCormick Tribune Ice Rink inside the park is the place to go. You can rent some skates and take in gorgeous views of the city at the same time.
When you are finished, head to the Cloud Gate sculpture to see the city in its reflection. Cloud Gate, also referred to as “The Silver Bean,” is a sculpture made of highly polished stainless steel that reflects the city’s skyline and the clouds above beautifully.
To satisfy my desire to get in the holiday spirit, we headed to the Navy Pier, a famous pier on the shoreline of Lake Michigan featuring restaurants, exhibits, and a 15-story tall Ferris Wheel. During the holiday season it hosts Winter WonderFest, a family friendly indoor playground and skating rink. After admiring the Christmas decorations inspired from countries around the globe, we headed to a bar on the pier for some locally brewed beers. The beers got us ready to brave the Ferris Wheel in the cold! (For any fellow “Divergent” fans out there, this is the Ferris Wheel featured in the book and movie.)
The best views of the city are from the John Hancock Center and the Willis Tower. Depending on weather and visibility the lines can be long, so if you have limited time you may want to choose one. We chose to do both! We toured the Willis Tower’s Skydeck Chicago during the day.
It has glass ledges you can step out on, unless your fear of heights gets to you. On our final night we had drinks at the Signature Room, located on the 95th floor of the John Hancock building. The city views at night were beautiful!
If you want to experience some culture on your trip, head to some of the Polish neighborhoods. Chicago is home to the second largest Polish population outside of Poland. Being Polish myself, this was on my “must do” list. On our trip we stopped by the Polish Museum of America, picked up a Christmas card written in Polish for my grandma at a local store, and of course sampled the food! I suggest eating at Podhalanka if you are interested in trying a variety of home cooked Polish food. The owner suggested we order a sampling of many of traditional dishes. What he brought out was authentic, delicious, and plentiful!
For nightlife, we saw the Book of Mormon at the Bank of America Theater. This show is coming back in February of 2015, but if offensive humor is not for you the city has a variety of shows and venues to choose from. A short train ride away we also hit up The Second City, a comedy club specializing in sketch comedy and famous for getting many of the big SNL stars their start. We started with a holiday themed show and enjoyed it so much we decided to forgo seeing one of the other shows around town and opted to go back for a second show.
We ended our last night with a romantic horse and carriage ride. While it was romantic, the wait was quite long. This was the only time I really felt too cold to be outside.
To date, Chicago is one of my favorite winter destinations. Okay… to be fair, I did get engaged at the end of this trip, but trust me, if you don’t hate the cold, don’t count Chicago out this winter!
This Guest Post was written by Flirting with the Globe contributor, Becky Jackson. You can learn more about Becky here.
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December 10, 2014
We will be moving to Chicago in January!! Thank you for the great information. It is a new city for both of us so this will give us a kickstart for exploring the city.
-The Couple
Sarah recently posted…10 Reasons to Get Your Passport NOW!!
December 10, 2014
You’ll love Chicago! (I grew up 90 mins north in Milwaukee).
March 10, 2015
Amazing city all year round!!
March 10, 2015
I absolutely agree, Michelle!
November 15, 2016
That is a very decent list of things to do in Chicago during the winter. If you are also a sports fan, then I suggest visiting the Chicago Sports Museum. It only costs $6 to enter, but it’s a nice little interactive museum that highlights some of Chicago’s best sports teams, athletes, and moments.
There is also a nice tribute to legendary Cubs’ announcer, Harry Caray, as well as a section dedicated to sports curses and folklore. The Steve Bartman ball from the 2003 NLCS series – which “allegedly” led to the Cubs’ downfall in both Game 6 and Game 7 – is also displayed here in a glass case in all its blown up glory. 🙂
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November 16, 2016
Thanks for the info, Ray!
July 30, 2017
It sounds like you did it right. I always tell people not to come here in the winter, but in December it’s actually quite nice. And you have the added charm of the holidays. After that, though, it gets colder and uneventful for all of January and February. In the dead of winter, I’m either hibernating in my apartment or looking for a weekend getaway somewhere south on a budget.
One thing you should try if you come back is the Christkindlmarket. Lots of German food and Gluhwein to keep you warm.
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July 31, 2017
Great suggestion – thanks, Dan!