Things To Do in Chicago in the Winter

Chicago winters are brutal, so here are some activities that keep you warm indoors but also let you have an enjoyable season because we can only binge-watch so many shows during the months of January – April, amirite?

TopGolf Swing Suite 

Don’t dismiss the TopGolf Swing Suite just because you just aren’t that into sports. This luxury simulation sports bar is literally for everyone. There is a multitude of games that aren’t golf-related that you can play on the simulator like zombie dodgeball, soccer, baseball, and even carnival games. I took my dad’s family for our annual holiday party last week and it was a huge hit with kids and adults. Another reason I love this place are the food and drinks. I’ve been to TopGolf out in the suburbs and the food is good don’t get me wrong, but it isn’t Aster Hall level delicious. Aster Hall is a food hall in the 900 Shops on Michigan and they have actual Small Cheval burgers! The elote and the pizza are also delicious and it can all be catered for your private party at the Swing Suite. It’s also a casual bar so you can just pop in for a drink before or after shopping!

Time Out Market 

A personal favorite pastime of mine is just eating and drinking. In the summer it’s easy to bop around to different places to eat and drink, but in the winter it’s too cold to go even one block which is why my favorite new place is Time Out Market Chicago. Any food hall might do in a pinch, but this place stands out because of the amount of seating and the abundance of options there are. You could come for lunch, drink, stay for dinner, and then have dessert. Come with LOTS of friends so you can try one of everything, but my favorites are the dumplings by Urbanbelly and the brussel sprouts by Band of Boehmia.

Block 37 + Hot Tix 

I love going to the theater, but it can get expensive so hitting up a Hot Tix booth is something my family and I do pretty frequently when we are visiting other cities. Luckily, Chicago has one right on the first floor of Block 37 on State Street and this holiday season my dad and I used the booth to get tickets to a show at the Goodman Theatre which is right across the street! They have tickets to all sorts of shows though including things on the north side of the city so it’s worth checking out for deeply discounted tickets!

Igloo/Winter Cabana Rentals 

I did one of these for my birthday a few years back, but heated plastic igloos have become the hottest thing of winter 2020. You can find them at the following places and you’ll have to contact them for pricing but we paid $200 + a minimum spend threshold based on how many people were in the igloo for two hours when I did it at iO Rooftop at the Godfrey: Barcocina, City Winery on the RiverWalk, iO Rooftop at the Godfrey, and Hotel Zachary.