The Coolest Things to do in Chicago in Winter!

The Best Winter Chicago Itinerary To Copy

Chicago is where I call home and in this guide I’ve gathered all my favorite things to do in this amazing city during the colder months. Whenever I have friends or family in town when our winter coats are out, I put this guide to the test and it is a great way to see all that Chicago has to offer!

The beautiful Chicago theater on a snowy day

Where to Stay

LondonHouse Chicago: Location is everything when visiting in the winter and you want a spot that will allow to enjoy Chicago year round. LondonHouse is in the heart of it all right on the river and walking distance or a train ride away from everything in Chicago! This was my number 1 place to stay when I would come to the city and in the winter they have an amazing outdoor rooftop setup that is totally winterized with heaters and igloos so you still get those infinite skyline views!

Cabra Winter Rooftop Bar — The Hoxton Hotel’s incredible rooftop bar and restaurant Cabra is the perfect winter spot

The Hoxton Chicago: West Loop and Fulton Market has the best restaurants and bars in the city and staying in the heart of it all is a great choice at the very trendy Hoxton. The Hoxton has three incredible spots to hang out in the building, but my favorite year round in the plant filled beautiful rooftop Cabra that makes you feel like your in a greenhouse with epic city views!

The Best Winter Things to Do in Chicago!

The Bean, Millennium Park and Ice Skating: A great way to start off your trip is checking out the iconic Bean in Millennium Park! Another awesome winter activity is ice skating right next to the Bean and around the Maggie Daley Ice Skating Ribbon which is a beautiful route through the park!

3 Arts Cafe: Inside the stunning RH store is a true gem of Chicago year round. Transport yourself into a gorgeous greenhouse cafe that has chandeliers, a fountain, trees and comfortable seating. In the winter you will feel like your inside the prettiest snow globe! Check out the rooftop area after dinner too

The Art Institute of Chicago: One of the best art museums in the world, the Art Institute is a can’t miss! Grab the guide provided to see all the masterpieces in the museum or hop on a guided tour. There are so many iconic pieces of art and also a great gift shop!

Time Out Market: Head to the super trendy Fulton Market neighborhood where all the best luxury high-rises and new restaurants are in the city. Time Out Market is a great place to grab some amazing food from local restaurants all in one place. You can pick and choose different global eats for a great meal in a lovely atrium, huge bar, and also a rooftop bar!

Untitled Super Club: This River North restaurant doesn’t look like much from the street but as soon as you walk down the speakeasy-esk stairs you are immediately transported to a super cozy and elegant spot. Velvet green walls and moody lighting make for a great setting & they also serve amazing drinks and food. I recommend a reservation for this one and stick around after dinner to check out their live music!

Bundle Up and Stroll the River Walk: The Chicago River is the heart of the city and is beautiful any season. Grab your best coat, bundle up and catch the twinkling lights of this magnificent city!

Explore Lincoln Park: Lincoln Park is a must see on any trip to Chicago no matter the season! Check out the Zoo Lights in the always free Lincoln Park Zoo and warm up in the many indoor animal exhibits. Then wander your way over to the also free Lincoln Park Conservatory! Grab a hot chocolate and enjoy why Chicago is a “city in a garden”

Three Dots and a Dash: The coolest tiki bar will surely transport you right to warmer weather! This awesome bar has beautiful cocktails and the space is such a fun vibe.

Get Your Game On: Chicago has so many fun activity bars that are even better in the winter! Check out Puttery which has two super cool indoor put-put courses (reserve a time here). For retro gaming fun head to Emporium Arcade Bar or Headquarters Beercade, a great thing about Headquarters - all the games are free! If bowling or Bocce is your thing Pinstripes or Punch Bowl Social are fun and vibey spots. And for the activity you didn’t even know you needed in your life - the SUPER fun Whirlyball - Whirlyball Chicago is a must try!

The Field Museum: A gorgeous museum with so many interesting permanent and rotating exhibits. Its a great place to spend a cozy cold day! The famous “Sue” T-Rex is housed here along with other beautifully displayed dinosaurs

**Ginger tip**: The Alder Planetarium right next to the Shedd and Field has a great cafe with incredible views of the city. Eat a quick and easy lunch then snap some incredible shots of the city before ducking into your next museum.

The Shedd Aquarium: What better way to spend a winter day then being transported to magical underwater worlds! There’s so many beautiful wings and aquariums that look like art. There’s also Beluga Whales here which I love watching play. The aquarium also offers a bunch of cool behind the scenes tours and one lets you play with the Belugas!