Top 5 Chicago Winter Activities

When I get asked where I live, the typical response is “That’s awesome! But gross, how do you survive the Winter there?” Regardless of how amazing Chicago is, everyone is concerned about what happens once it starts getting chilly.

Winter in Chicago definitely has it’s ups and downs. While the snow can be beautiful, the negative wind chills can be unbearable. The options for activities significantly decrease, and it seems all that’s left to do is eat…and drink. Some people brave the winter storms and miserable traffic, but most people opt to stay in the comfort of their home, even on the weekends.

This is now my fourth winter in Chicago and honestly, it doesn’t get any easier. Once the cold rolls around, I still dream of moving to that warmer climate where I can play sand volleyball and drink on patios year-round. But I’ve come up with ways to cope in this nasty weather, and I remind myself how great it is to live in this city. It also makes me appreciate Spring and Summer-time Chi much, much more!

This post is for my fellow Chicagoans and those tourists that dare find themselves in our lovely city in the dead of Winter.

Here are my favorite Chicago Winter Activities:

1. Pizza & a Movie

Everyone knows that Chicago is famous for it’s delicious deep-dish ‘za. Most people rush to Lou Malnati’s or Giordano’s or Gino’s East. While their pizzas are amazing, I like to recommend a hidden gem in Lincoln Park that’s better than the big names – Pequod’s. Pequod’s serves up the famous pan style pizza with an awesome twist of caramelized crust. I’ve never had a bad pizza there and always leave feeling full and happy. The cool thing about Pequod’s is that it’s right across from Regal Webster Place 11, a movie theater with assigned seats that recline. So after enjoying a delectable Pequod’s pizza, walk the two minutes over to Regal and enjoy a movie. This activity requires minimal time outside, thus making it a perfect thing to do in the Winter. (Tip: You can order your pizza ahead of time, so it’s almost ready when you get there AND you can make it to the movie on time!)

Pequods Pizza courtesy of
Pequods Pizza (photo courtesy of


2. Belly Up at a Cozy Bar

Chicago has plenty of bars that can make you feel right at home. From the friendly service to the decor to the fireplaces, you won’t mind taking a short trek in the cold to your favorite bar for a drink. Once inside you forget about the negative 45 degree temperature on the other side of the glass and enjoy time spent with your friends. One bar I recommend if you’re wanting the cozy-vibe is Soho House in the West Loop. They have big fancy couches, lounge chairs and candles lit for the perfect atmosphere. You’ll feel like you’re in your own fancy living room! Soho House is also home to four other public bars and restaurants, so you can change up the setting and really stay a while without going outside!

Fox Bar at Soho House
Fox Bar at Soho House in West Loop

If drinking isn’t your thing, finding a nice coffee shop to warm up and be productive in is also another one of my faves. Recently I stumbled into Asado in River North and loved sitting by their fireplace with a hot cup of jo!

Asado Coffee
Asado Coffee in River North


3. EAT… A Lot. Everywhere you can really. 

Of course eating is a huge activity for me, regardless of the season. In the Winter though, I am able to pick it up a few notches. I like to try new restaurants and new recipes every now and then, and Winter is when I find the time to do it! I now have no excuse as to why I can’t go out with a friend or why I don’t have time to cook a meal. I’m not traveling as much, I don’t have weddings to go to every weekend and I don’t have volleyball. I try to scratch off the places on my to-go list, even when it’s freezing. Already this season, I’ve been to some great restaurants I’ve been wanting to try for a long time!

Beef Brisket at Fat Willys BBQ
Beef Brisket at Fat Willys BBQ in Bucktown
Sushi Dokku
Sushi Dokku in West Loop
Ramen San in River North
Ramen San in River North

I’ve also been trying out a couple crock pot meals (who hasn’t this year? they seem to be all the rage). The crock pot is just perfect for the Winter and it makes sense! I’ve made a breakfast casserole, potato soup and a southwestern chicken dish. Recipes are to come in my #goodeats section, but enjoy a picture of my southwestern chicken chili. Hot and healthy!

Crock Pot Southwestern Chicken
Crock Pot Southwestern Chicken


4. House of Blues Concerts

House of Blues in River North is always a good time. They offer a variety of different shows and concerts, and a gospel chicken and waffle brunch on Sunday! I’m a huge fan of live music, and I enjoy the smaller venue that House of Blues has to offer. It’s the perfect Winter activity to get you out of the house and into a fun, upbeat environment. Forget about the snowflakes and rock out to your favorite band!

Backyard Cohort at House of Blues
Backyard Cohort at House of Blues


5. Blackhawks Games

Not going to lie, I was not at all into hockey before I moved to Chicago. After attending my first Blackhawks game, all that changed. I got goosebumps listening to the guy sing the National Anthem, especially with how into it the crowd gets. I think it’s something everyone should experience at least once. I love going to these hockey games, not only for the beer and National Anthem, but the action in the game is always so exciting. It’s fun to see your city rally around a common interest. Hockey spans from October to April, so if you’re in Chicago in the Winter, there’s bound to be a game to go to! It’s loud, but Blackhawks games are awesome.

Blackhawks Opening Night Game
Blackhawks Opening Night Game


I now realize my favorite Winter activities aren’t quite the healthiest, but they are the most fun for me if I can’t be outdoors. What’s your favorite (Chicago) Winter activity?

I'm Abby - a weekend getawayer, lover of beach volleyball, grilled cheese enthusiast and puppy dog admirer.

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