From helicopter tours to holiday traditions, there are plenty of things to do in Chicago other than hibernate. We’ve rounded up a list of the top 10 things to do in Chicago this winter. 

Chicago Winter Bucketlist: Top 10 Things to Do

1. Ice Skating

Millennium Park and Maggie Daley Park (pictured)  both have ice skating rinks with impressive backdrops: Chicago’s skyline. Skating is free with your own skates, otherwise, you can rent some at the rink. The lines can be crazy long on weekends, especially when it’s not painfully cold, so try a weekday if you can. Holiday bonus: If you go to Millennium Park on Friday nights, you may catch some carolers at Cloud Gate.

Skates cost $13 on weekdays and $15 during the weekends and holidays. At Maggie Daley Park the price is $12 on weekdays and $14 on weekends and holidays. Both rinks open mid-November and run until about mid-March, weather permitting.

2. Try Chicago’s Hottest Restaurants

 

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A post shared by S.K.Y. (@s.k.y.restaurant) on Sep 17, 2018 at 7:25pm PDT

 

One of the best things to do in Chicago is to eat! It is foodie heaven up in here! Make a reservation at some of Chicago’s hottest restaurants such as Etta, Pacific Standard Time, or S.K.Y.

Etta in Wicker Park offers housemade pasta and pizzas made in a wood-fired hearth. The ice cream desserts are also bomb, BTW! Pacific Standard Time is a popular new California-inspired restaurant in River North from the chef who used to work at Nico Osteria, and S.K.Y in Pilsen offers an Asian-Mexican fusion menu in a moody, industrial atmosphere. 

3. Zoolights

More than two million lights illuminate Lincoln Park Zoo for this festive annual event. Enjoy ice carvings, zoo animals, and ice skating under the glow of Christmas lights. It’s free and you can bring or buy hot cocoa (spiked, if you wish!).

Opening night is Nov. 23 and they have tons of special events throughout the holiday season — including Monday Family Nights where kids eat free at the Park Place Café, and Adults’ Night Out where you can stroll the zoo grounds after hours with a drink in hand. You can get more information and find tickets for the events here. Zoolights end Jan. 6, 2019.

4. Check out a Concert

With so many venues in and around Chicago (House of Blues, Lincoln Hall and Double Door to name a few), there are always fantastic musical acts in town. Here are a few acts coming to Chicago this winter to check out: Daughtry (Dec. 7), Chicago Symphony Orchestra: Harry Potter and the Chamber of Secrets (Dec. 8, 9), Pentatonix (Dec. 11, 12), iHeartRadio Jingle Ball feat. Shawn Mendes, Calvin Harris, Dua Lipa and Alessia Cara (Dec. 12), John Legend (Dec. 13) and Chicago Symphony Orchestra – Merry, Merry Chicago.

5. Helicopter Tour

Talk about a bad-ass date night! Chicago helicopter rides showcase spectacular views of the city when the sun is up or down, and there are even some that show off the city’s holiday lights. Check out this post about Chicago helicopter rides here for a complete guide. You’ll get an overview of pricing, the landmarks you’ll see, and coupons for popular tour companies in that guide. I even put together a video of my experience taking a Chicago helicopter ride. 

6. Take the Plunge along with Celebrities!

Every year, hundreds of people – including some A-list celebrities – jump into Lake Michigan to raise money and awareness for Special Olympics. My friend from the Best Buddies program is a Special Olympics athlete, so I was happy to take the plunge! The photos above are from 2016 when I ran into a few celebs who also took the plunge, including Lady Gaga, Sophia Bush, and David Eigenberg (I loved watching him as Steve in Sex in the City!). The next Polar Plunge is Jan. 26, 2019, and registration is open now!

7. High Tea

 

Put on your fancy pants, grab your girlfriends, and sit down for high tea at one of Chicago’s luxury hotels. The Drake, The Peninsula, and The Langham serve afternoon tea in the most beautiful, festive settings. I went to Holiday Tea at the Drake with some friends and it was fun to get dressed up for a fancy afternoon. The Drake offers all-natural flavored teas served with finger sandwiches and scones. I was happy they had lots of gluten-free options! The cost for high tea at The Drake is $52 for adults and $25 for kids.

8. Christkindlmarket

Every year, Chicago’s downtown square, Daley Plaza, transforms into an outdoor holiday market packed with handcrafted gifts including ornaments, nativity sets, and wooden treasures. Christkindlmarket is inspired by the Nuremberg Christmas Market in Germany, so you can find schnitzel, strudel, and beer. You can also sip mulled wine in one of the souvenir mugs while you stroll through the holiday market. Christkindlmarket runs from Nov. 16 until Dec. 24, 2018.

9. Drink Champagne in the Walnut Room

A lady lunch at the Walnut Room at Macy’s is another holiday staple. The room is decorated so beautifully, including a massive tree! There is also a great drink list with holiday-themed cocktails served in souvenir mugs. My girlfriends and I go here every year in December. This is the seventh year in a row, actually. We catch up over champagne and holiday cocktails, then go outside to see Macy’s holiday windows. (It still feels weird saying Macy’s. RIP Marshall Fields windows).

10. Ride Navy Pier’s Winterized Ferris Wheel 

Navy Pier upgraded its ferris wheel in 2016, and now it’s bigger and better than ever. You can take a luxurious ride in the new VIP gondola which has a glass bottom so you can soak in the views of Lake Michigan and the skyline from all angles. The new wheel has heaters, so you can comfortably go for a ride even on a cold winter night. Watch my VIP experience on the ferris wheel for a glimpse of the epic views! 

 

Be sure to pin this image if you are planning a trip to Chicago this winter!