Looking for Things to do in Chicago?

Well, you've arrived! There's a lot of fun to be had in the 312 in the winter - Check out our "highlight reel" of things to do in Chicago below. And don't forget to check out Chicago's famous attractions and landmarks like The John Handcock Building and the 360 Chicago Experience - and the Willis Tower Skydeck for sky high views of the city. Check in with BLOG too some great insider tips on all things Chicago!

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ONGOING
If you're as big of a fan as we are of The Bear on Hulu - you MUST check out Yes Chef! Chicago. A Bear inspired Food Tour. You'll get to taste the places where Carmi and his gang frequent - and it's all delicious!

NOW - JAN 19
Back again by popular demand, Choir of Man returns to the Apollo . . . If you missed it the first time, Or even if you didn't) get to this high octane show, stat!

NOW - FEB 2 / MARCH 9
If you love the feel of gold steel on ice, get yourself to the McCormick Tribune Ice Rink at Millennium Park now through Feb 2, OR the Maggie Daley Skating Ribbon. They're both an energetic way to spend a chilly afternoon with the gorgy skyline as your backdrop!

NOW - JAN 2026
If you want to laugh 'til you cry, Check out Drunk Shakespeare at The Lion Theatre. The NYT called it "Boozy rowdiness and debauchery"

JANUARY

JAN 17 - JAN 19
It's CUBS CON 2025 . . . or as many know it as - the Cubs Convention 2025. Meet your favorite players, get behind the scenes scoops, spend your dough on amazing auction items! It's all Cubs all day for 3 whole days!

JAN 18
If you loved the film, you'll love the concert experience! Check out Marvel's Black Panther in Concert at The Auditorium Theatre!

JAN 23
Feeling like plugging into concert mode? Check out Kelsey Ballerini at the United Center. One night only!!

JAN 24 - FEB 9
Every time is a good time to eat out in Chicago - But Chicago Restaurant Week takes the cake! Check out your faves, or discover something new.

JAN 25
Check out Pat McGann Live at the Chicago Theatre. Enjoy a few laughs with friends at one of Chicago's most iconic theeatres!

FEBRUARY

FEB 6 - FEB 16
Chicago Theatre Week returns with a ton of new shows for a fraction of the cost! If you love theatre - start planning your theatre adventure right away! Now who's being dramatic?

FEB 8 - FEB 16
Get your motors running - and drive to the Chicago Auto Show. at McCormick Place. And hey, if your significant other is a car buff, this might be an excellent Valentines Day option! Just sayin' . . .

FEB 12 - FEB 15
Taylor Tomlinson takes the stage for 3 nights at the Chicago Theatre for her 2025 Save Me Tour. Book 'em now, because their going fast!

FEB 14
With 4 Grammy nominations and 5 gold and Platimun records, Jeffrey Osbourne comes to the Auditorium Theatre for 1 night only! Book a night with this classic!

FEB 15
Get your tickets now (or find someone who has them for Foster the People at The Salt Shed. One night only - don't miss this!

MARCH

MARCH 14
Check out Mary J Blige at the United Center. She only here for one night, so find your ticket now!

MARH 15
Save the date for one of the biggest parties of the year! St Patricks Day celebrations in Chicago! Between the Chicago River dying, the pub crawls and parades, well, lets just say, you're gonna need to rest up for this weekend!

MARCH 24
Throw it back for a night with Iggy Pop at The Salt Shed. Chicago loves a classic - so we're pretty sure this show will be fire!

TAKE A CULTURE TRIP!

Some of Chicago's greatest cultural institutions are now welcoming back visitors! HOORAY! Of course, visitors can once again enjoy the plethora of cultural experiences that Chicago has to offer. Of course Chicago has a wealth of cultural experiences just waiting for you. Check out some of Chicago's world famous museums like the Field Museum, Shed Aquarium, Art Institute, Museum of Contemporary Art. Or let your imagination run wild at the Wndr Museum and the all new Museum of Ice Cream. Spectacular!!

CHICAGO IS A SPORTS TOWN!

Fact. Chicago is a huuuuuge sports town, and as we head into fall and winter exciting times are on the horizon. Soon the Cubs will be calling it a wrap for the season along with the Chicago White Sox and Chicago Sky. But the Chicago Bears and Soldier Field are open for business, the Blackhawks are about to take to the ice at United Center! Plus, it's coming upon squeaky sneaker season as the Chicago Bulls soon take the court. There's always something to root for - and we can't wait!!

TURN IT UP!

If you love music, there's nothing better than LIVE Music in Chicago! Chicago's stages are open and bands are scheduled to rock your world! Check out some of our favorite venues like Lincoln Hall, Schubas, Thalia Hall, The Metro, The Vic, The Green Mill, and tons more!

Enjoy the Great Outdoors

The famed Chicago Architecture Tour is ready to guide you on an epic journey of discovery . . . Truly! You'll see some beautiful sites, enjoy a cocktail, and a "cool" river breeze in the heart of Chicago. Other Riverboat cruises are available too, check out Shoreline, Wendella, Mercury, and a ton more!

We're so lucky that Chicago has some of the best city parks and outdoor spaces in the World, and now is a great time to appreciate them in all of their splendor! Take a stroll through Millennium Park and The Bean, Grant Park, or Lincoln Park and see the dramatic backdrop of the city behind them. Or check out the Chicago Riverwalk and enjoy some outstanding public art and sculptures, eat, drink, and listen to live music! Feeling robustly athletic? Get yourself to the Lakefront Trail with a rented divvy or your own two feet! And if you're an animal lover, the residents at Lincoln Park Zoo are waiting to give you a warm welcome.

SHOPPING, ANYONE?

Chicago stores and boutiques are open for business. If you fancy a new winter wardrobe, or just some browsing, you'll find most major retailers and boutiques are open. Just be sure to mask up and keep your distance!

DO YOUR THING - DIFFERENT! Check out our curated list of cool attractions

If you love the great outdoors, get yourself to the 606. An elevated jogging/hiking/biking path that takes you through some of the 312's most interesting neighborhoods like Bucktown, Wicker Park, Logan Square, and others.
Bike your way through town on a Divvy. Those are the blue bikes you see pretty much everywhere . . . We suggest a ride up the Lakefront, coz it will net you some pretty awesome instagram shots!
If you've been dying to check out EATALY, you're in luck - it's a block away, and yeah, it's awesome. It's a bustling Italian marketplace that offers some of the freshest fare and authentic Italian foods around. Foodies won't want to pass it up.
In season, there are few things cooler than getting out on the cool waters of lake Michigan on your own (rented) jet ski, and worth e-v-e-r-y penny! Or one with the river in your very own kayak. Here you'll get some of the best views of the city, and get in a pretty decent workout too. Of course, both are seasonal.
Check out the Riverwalk (hint: it's on the river), and check out the peeps walking and cruising by. It's a great stop for a cocktail, or just to brown bag it.
What better way to hold on to a memory than with body ink? Deluxe Tattoo is one of the best tattoo shops in Chicago. We just recommend you visit sober - you know, no regrets and all.
Everybody's heard about the Architectural Boat Tour, now go out and do it. It is def. one of the best "attractions" in Chicago.

CHICAGO'S MUSIC SCENE

If you dig music, you've come to the right city. In addition to the major arena's, Chicago boasts a ton of awesome, more intimate venues that often book the cutting edge talent on the cusp of stardom. You may also see them at one of Chicago's major music festival during the summer. Here is a short list of some of the best venues in the 312 to sit back and jam. - These even made TimeOut Chicago's best list!

Thalia Hall
The Vic Theatre

Riviera Theatre
The Hideout