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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