Chicago in the Winter: How to Enjoy the City at its Most Freezing Temps

Back To Blog

Summer in Chicago is great: endless restaurants with beautiful open-air seating, patios filled with twinkling lights and great music, movies in Millennium park, the list could go on. However, what many don’t realize is that the winter can be just as enjoyable if you know what you are doing. That is why we are here to help! Here are five fun, cheap (for the most part) and unique activities to do in those frigid winter months.

1. Winter-themed Chicago Nightlife

Now, you may be thinking “winter nightlife? You mean my cozy blanket and TV at home?” Yes, that is what a lot of us do when the temperatures plummet and going outside is a little scary. BUT there actually is such thing as winter-themed bars and restaurants that hide out amongst the rooftop spots and open-air seating. One of these must-see bars is called Guthrie’s Tavern located in the quaint Lincoln Park neighborhood. It’s your typical hole in the wall spot but has a wall of board games, warm drinks and an all-around cozy vibe that makes you feel like you could be nestled in the mountains. Another killer spot is located on the north side of Chicago along a popular street known to many locals. The Red Lion Pub is definitely made for those cold winter nights when you want to relax in a big, comfy chair and pretend you are in a Harry Potter movie. Whether you are by yourself, with your family or a group of good friends, this pub has something for everyone.

2. Maggie Daley Park Ice Skating

Want an outdoor activity you can enjoy ALL season long, over and over again? Well, look no further than ice-skating the “ribbon” at Chicago’s Maggie Daley Park. Located smack dab in the heart of the city, a winding path of ice takes you on the ultimate outdoor excursion. Between hot chocolate, a unique landscape and the Chicago skyline in the distance, this is a winter experience you just cannot pass up! Admission is free, however, if you have to rent skates you will have to pay a small fee. Don’t worry; the Ribbon is definitely worth the few bucks!


3. Blackhawks/Bulls games at the United Center

Now, for those who can afford it, Chicago’s NHL and NBA teams PACK up the United Center and put on quite a show almost every night. The Blackhawks play well into the spring months giving you many opportunities to watch them work their hockey magic. Can’t make it to the game(s)? Yeah, us either. Thankfully there are plenty of Bulls and Blackhawks themed bars/restaurants that will create a atmosphere that is almost as good as the real thing.



4. Chicago Pedway

Do you want to walk famous streets like State, Michigan or LaSalle but are worried it’s just too cold out there? That is where the Chicago Pedway comes in. Underneath those streets lives a maze of hallways spanning around 40 blocks of downtown Chicago. Take a left and you’ll end up at a restaurant that serves upscale cocktails and appetizers. Take a right and you will end up at a popular department store. You can essentially walk an entire “street” without having to be outside! The best part? The Pedway offers organized tours, many tourist attractions, and of course, shopping!


So, there you go: four very fun, very different activities to do in Chicago during the coldest months of the season Spaces style.


Next Article

5 Downtown “Hidden Gems” That Guarantee A Great Night Over and Over Again