Top Things to Do in Chicago

About the City

Nestled on the shores of Lake Michigan, Chicago is a city brimming with towering skyscrapers, deep-dish pizza, and a cultural scene as vibrant as its history is rich. Dubbed the 'Windy City', not solely for its breezy lakefront but for its historical political verbosity, Chicago invites you to be blown away by its dynamic vibe. Architectural aficionados can marvel at the cityscape from the Willis Tower Skydeck, featuring heart-stopping views minus the gusts! Culture hounds, on the other paw, will find solace in the Art Institute of Chicago, home to classics that span centuries. But it's not all jazz and jovial jaunts in this metropolis; winters here pack more than a punch, with frigid temperatures that would have even polar bears begging for a sweater. And while the city's love for sports is legendary, the frustration when hometown teams underperform is equally monumental. Summers offer a respite with festivals galore, where the sounds, tastes, and peoples of the world converge on Chicago's streets. Yet, these same streets face challenges, grappling with congestion and a reputation for notorious traffic - a test of patience and a puzzle that no deep-dish pizza can solve. Regardless, whether basking in the sun at one of the many lakefront beaches or bracing against the winter chill, Chicago's spirit remains indomitable - an urban dance of chaos and charisma.

Things to Do in Chicago

Chomp on Some Pub-style Pizza

Food & Drink

Nosh your way into the night with a crispy-edged, tavern-style pizza unique to Chicago's bar scene! It's pipin' hot with a thin crust that snaps like a cracker when you take a bite.

Picnic with a Skyline View

Outdoors

Grab your favorite munchies and a cozy blanket, and head out to one of Chicago's stunning parks for a picnic with a view. With the city skyline as your backdrop, it's the perfect setting to chill and ...

Get Lost in a Magic Maze

The Unexpected

Ready to escape reality for a bit? Navigate the enchanting twists and turns of a living hedge maze! Conquer it solo or race your buddies to the other side. Pssst, it's totally okay to pretend you're i...

Craft Your Own Bean Blend

The Unexpected

Unleash your inner barista and create a coffee blend that's uniquely yours. From roasty toasty to smooth and sweet, mix 'n match beans until you've got the perfect morning wake-up call cuppa!

Whistle a Tune in a Whispering Gallery

The Unexpected

Ever whispered secrets in science class that teachers never heard? Now's your chance to relive the fun! Find a whispering gallery and share secret messages from across the dome – it's invisible string...

Pedal Your Way Through a Surreal Art Gallery

The Unexpected

Why stroll through art when you can pedal? Get on a bike and cycle through art installations and funky exhibits at Chicago's very own creative wonderland. It's like a choose-your-own-adventure book, e...

Beach Volleyball

Outdoors

Spike, dive, and jump with your squad or make new beach buds. Get that dig set spike routine on point while catching some rays!

Picnic at the Park

Outdoors

Grab your checkered blanket, pack some munchies, and relax under the Chicago sky. Perfect for a chill day soaking up the greenery amidst the urban jungle.

Jog Along the Lakeshore Path

Outdoors

Lace up those running shoes and hit the scenic lakeshore path for a jog with a breeze. Not a runner? No sweat! You can walk, bike, or even rollerblade with Lake Michigan's sparkling water cheering you...

Go Off-the-Beaten-Path in the Urban Jungle

Outdoors

Take an adventurous bike ride or hike on the North Branch Trail System. You'll forget you're still in the city as you explore the forest preserves, babbling brooks, and local wildlife. Don't have a bi...

Snack on Chicago-Style Popcorn

Food & Drink

Your tastebuds can't miss out on the symphony of sweet caramel and savory cheese popcorn mixed to perfection! It’s like a flavor parade in your mouth with each handful.

Tour the Roaring Twenties at the Chicago History Museum

Sights

Flapper dresses and gangsters, oh my! Step back in time and get schooled on the Windy City's past with a dash of sass and plenty of class.

Watch a Spectacular Show at The Chicago Theatre

Sights

Get ready to ooh and aah at The Chicago Theatre. Snag a ticket to a show at this iconic venue and let the showbiz magic sweep you off your feet!

Stroll Through Time at The Art Institute of Chicago

Sights

Unleash your inner art critic and wander through one of the oldest and largest art museums in the USA. The Art Institute of Chicago isn't just about looking at pretty pictures; it's a time machine wit...

Gaze at the Starry Night at Adler Planetarium

Sights

Craving a cosmic experience? Blast off to Adler Planetarium where you can snoop around the universe without leaving the comfort of Chi-Town. It's literally out of this world!

Snap a Selfie with the Flamingo at Federal Center Plaza

Sights

It's big, it's red, and it's flamboyant! We're talking about the Flamingo sculpture in Federal Plaza. Give your legs a stretch, and take a quirky pic with this abstract art piece.

Spin on a Spicy Sport Pepper Journey

Food & Drink

Get ready to have your taste buds dance to the tune of some spicy sport peppers! Now, we ain't just talkin' any peppers - these Chicago favorites are the secret zing in a classic Chicago-style hot dog...

Feast on a Fat Shallot Sammy

Food & Drink

Prep your belly for an 'OMG yum' moment with The Fat Shallot's signature sandwiches! Think golden, crispy chicken with spicy aioli or melts that'll make your heart sing.

Dig into a Duck-Fat Dog

Food & Drink

Treat yourself to a luxurious twist on a Chicago classic: a hot dog elevated with rich duck fat. It's a lip-smacking blend of posh and party on a bun!

Be a Pinball Wizard

The Unexpected

Skip the slots and hit the flippers! Show off your pinball prowess at arcades with vintage flair. While the bells and lights dazzle you, keep that silver ball rolling – high score wins bragging rights...

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