Looking for some fun winter activities to do in Chicago?
Don’t let the occasional winter weather advisories deter you, there are countless ways to get out and explore Chicago even when the temperatures drop. We’ve included some of our favorites down below, let us know if they make it on to your next trip’s itinerary!
Ice skate at Millennium Park:
From November to March you can skate at the seasonal rink inside Millennium Park! If you’re already planning to visit The Bean, this is a perfect addition to your afternoon. The park is also a super quick walk from The Art Institute!
Enjoy a Winter Food Tour:
Despite the snow, Chicago’s food scene isn’t one to miss out on. Taking a guided food tour gives you the opportunity to sample iconic dishes while exploring diverse neighborhoods. There are plenty to choose from and most include dietary restriction options to make sure the whole party can enjoy!
Wicker Park has its own guided food tour that takes you to several nearby restaurants. You can try handmade smoked brisket pierogi at Pierogi Kitchen, unique burgers at Small Cheval or authentic French macarons at Alliance Bakery! For groups of 2-60, this tour takes about 3 hours and is a perfect option if you can’t decide where to eat first. To book this tour, click here.
From March 21-29, West Town Restaurant Week will offer diners a chance to enjoy exclusive discounts and pre fixe menus. Some notable participating business include: The Perch Kitchen + Tap, Bartoli’s Pizzeria, SUGOi Sweets, Un Amor, Oggi Trattoria and Forbidden Root. To check out the full list, click here.
Stroll down the Lakefront Trail:
Bundle up and enjoy the frosty beauty of the Lakefront Trail. Don’t worry, the 18 mile trail is salted and plowed from 6-11 every day, making it a safe place to catch glimpses of the snowy skyline and a sometimes frozen Lake Michigan.
Still feeling too cold outside? Take a trip to one of Chicago’s world-renowned museums:
The Art Institute of Chicago: Located downtown by Millennium Park, it’s easy to get lost in the halls of one of Chicago’s top righted destinations. With multiple levels and countless viewing rooms, this is a great museum to spend the entire day in!
The Museum of Science and Industry: Housed in the Palace of Fine Arts from the 1893 World’s Fair and home to unique exhibits (like the command module of the Apollo 8 spacecraft and a German U-boat from WWII), this museum is a perfect stop for fans of hands-on learning! Close to Lake Michigan and the UC campus, it’s a great spot for all ages and offers a wide variety of ways to pass the time.
The Field Museum: If you’re interested in dino’s, plants, gems and more - this is the museum for you. Wander through the Grainger Hall of Gems or get lost inside the current Pokemon Fossil exhibition!
The Museum of Contemporary Art: As one of the largest multidisciplinary contemporary art museums, there are a wide range of exhibits and artists to explore. This space is also known to host theatre and dance performances, so keep an eye on their yearly plans!
Let Wicker Park be your Winter Home Away From Home!
If you find yourself wanting to stay close to the inn, we are located right off Milwaukee Ave, there are tons of stops nearby to keep you busy. Here are just a few of our favorites:
Myopic Books is an incredible place to lose a few hours, with rows upon rows of over 60,000 books to flip through. As one of the city's largest used bookstores, there’s no way they won’t have what you’re looking for!
Vintage Underground, Crossroads Trading, Buffalo Exchange and Ragstock are just a few of the second hand shops ready to make your thrifting dreams come true. But if thrifting’s not your thing, don’t worry! Transit Tee’s, Mojo Spa, Una Mae’s, and Reckless Records are all within walking distance, too.
The Flat Iron Arts Building is right near the Damen blue line stop, just a short walk down from the inn. Inside what was once an office building, local artists now keep galleries that are free for the public to walk through. Definitely a must see for any of our art lovers!
The Den Theatre is a great place to catch small local and touring performances alike, ranging from comedy shows, musical artists, and trivia.
There’s nothing better than coming back to a warm place to rest and recoup after a day spent out in the city. The Wicker Park Inn is happy to provide a cozy, inviting home away from home to each of our guests, especially in the winter time!

