Bundling up to visit Chicago this winter? From ice skating to holiday markets, there’s still plenty to enjoy during our chillier months of the year.
1. Ice skating
Chicago is home to the largest ice skating ribbon in the U.S, Maggie Daley ribbon (named one of the “most architecturally beautiful ice skating rinks” by Architectural Digest). You can also find another rink with impressive city views nearby at Millennium Park. Both rinks can get crowded during the winter weekends, so be prepared if you have to wait a bit to get on the ice.
Admission is free at both rinks and skate rentals are available for $13 on weekdays or $15 on weekends.
2. Christkindlmarket
The Christkindlmarket is an authentic German-style holiday market right in downtown Chicago. I took this quote describing the market straight from the Christkindlmarket website because their marketing person clearly knows what they’re doing: “The smell of roasted nuts, fresh pretzels, bratwurst, and hot spiced wine, the sound of music, and the glimmer of sparkling Christmas ornaments, all in a cozy atmosphere.”
The market runs from mid-November to Christmas Eve, but be warned — it can get super crowded the closer you get to the holidays.
3. Lincoln Park Zoolights
Chicago’s Lincoln Park Zoo is one of the few free, yes FREE, zoos left in the U.S. Starting just after Thanksgiving, the zoo is decorated in over 2.5 million lights, making it a perfect spot to stroll around and visit the animals willing to brave the cold.
4. The Second City
Catch a show at The Second City, Chicago’s landmark comedy club home to notable alumni including Bill Murray, Mike Myers, Steve Carell, Tina Fey, Amy Poehler, Stephen Colbert… ok, I think you get it. Stop by a live show any night of the week and who knows, maybe you’ll be the first to see the next big SNL star.
5. Skydeck Chicago
It’s not a trip to Chicago without a visit to the top of the Willis Tower. The second tallest building in the western hemisphere and where you’ll find me in a cubicle Monday – Friday, the Willis Tower offers the highest public viewing area in the United States. On a clear day, you can see up to four states (Illinois, Indiana, Wisconsin, and Michigan) — although clear days are a bit hard to come by in the winter. However, it offers a spectacular view of the snow-covered city if you happen to visit during a snowfall.
6. City Winery
Ever wanted to drink wine in an igloo? Here’s your chance. Right on Chicago’s iconic river walk, City Winery sets up heated “igloos” that can be rented through the end of November. Reservations are needed, so you’ll have to plan ahead, but it’s a perfect way to celebrate your time visiting the Windy City.
7. Michigan Avenue
Michigan Ave, also known as the “The Magnificent Mile”, is Chicago’s iconic upscale shopping street, and is a super festive place to talk a walk (or shop ’til you drop) during the winter. Be sure to stop by one of the two Ghirardelli chocolate shops during your trip to warm up with a hot chocolate and a free chocolate sample.
Bonus: Starting on November 15 of this year, you can officially get your coffee fix at the world’s largest Starbucks — Starbucks Reserve Roastery Chicago. If you’re walking down Michigan Ave, it’ll be hard to miss.
8. Chicago Bulls game
I wouldn’t consider myself a big sports fan, but I love spending an evening at the United Center cheering on the Bulls. If you want to spend a few hours out of the cold, there’s probably not a more exciting way than enjoying the production of a Bulls game. Even if you’re not into basketball, Chicago Bulls games are known to have some of the best entertainment in professional sports (think incredible halftime shows).
And if you’re a hockey fan, don’t pass up the opportunity to see the Blackhawks if they’re in town.
9. Rooftop curling
You know that funny-looking sport in the Olympics where they’re frantically sweeping the ice? Grab a drink an give it a try at the Whiskey Business. Each winter they set up multiple curling rinks on their rooftop that can be rented by the hour. Try something new, have a good laugh, and make a reservation beforehand here.
10. River cruise
My favorite thing to do when a friend visits Chicago is hop on a river cruise for the best views of the city. Odyssey Cruises offers both lunch and dinner cruises throughout the winter (don’t worry, you’ll be indoors). It might be a bit of a splurge but you won’t regret the views. Check availability for your trip dates here.
Want to remember this list for your next trip to Chicago? Pin the image below!
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