Chicago is a city that constantly reinvents itself.
It is a world-class metropolis known for its stunning architecture, incredible food scene, and Midwestern charm.
But if you look past the standard tourist brochures, you will find a city full of quirky, thrilling, and completely exclusive experiences.
Sure, you can get deep-dish pizza in other cities now.
You can find great jazz clubs all over the world.
But there are some things that are so deeply ingrained in the DNA of the Windy City that they simply cannot be replicated anywhere else.
If you want to experience the real Chicago, you need to step off the beaten path and explore the hidden gems locals actually love.
Here are 19 things you can only do in Chicago (and nowhere else on earth).
Why Chicago is Completely Unique
Chicago isn’t just a “second city” to New York.
It is a city of firsts, a city of innovators, and a city of absolute characters.
This is the place that invented the Ferris wheel, the skyscraper, and the brownie.
Because of its rich, diverse history, Chicago has developed a culture that is fiercely local and incredibly proud.
When you visit, you aren’t just seeing sights; you are participating in a culture that exists nowhere else.
Let’s dive into the ultimate list of Chicago-exclusive experiences!
1. Take a Shot of Jeppson’s Malört (and get the “Malört Face”)
If you want to instantly earn the respect of a Chicago local, order a shot of Malört.
Jeppson’s Malört is a wormwood-based liqueur that is almost exclusively consumed in Chicago.
It is famous for being, well, absolutely terrible.
Locals describe the taste as a mix of grapefruit, gasoline, and bug spray.
Taking a shot of Malört is a true Chicago rite of passage, and the bizarre history behind the drink is just as wild as the taste.
The best part? Capturing the inevitable look of disgust on your friend’s face after they drink it, affectionately known as the “Malört Face.”
- 📍 Where to find it: Any dive bar in Chicago (try Richard’s Bar or The Owl).
- 💡 Local Tip: Have a chaser ready. You’ll need it.
2. Step Out on “The Ledge” (and TILT over the City)
Lots of cities have tall observation decks, but Chicago takes it to a terrifying new level.
At Skydeck Chicago in the Willis Tower (which is just one of many iconic Chicago buildings), you can step out onto “The Ledge.”
This is a glass box that extends 4.3 feet out from the side of the building.
You are standing on pure glass, 103 floors (1,353 feet) above the city streets!
If that isn’t enough of an adrenaline rush, head over to 360 Chicago at the former John Hancock Center.
Here, you can ride “TILT,” an enclosed glass platform that physically tilts you out and over the Magnificent Mile from 1,000 feet up.
- 📍 Where to find it: Willis Tower (The Ledge) and former John Hancock Center (TILT).
- 💡 Local Tip: Book tickets for sunset to see the city transition from day to a sparkling night grid.
3. Eat a Hot Dog “Dragged Through the Garden” (Without Ketchup!)
You might think you’ve had a hot dog, but you haven’t had a Chicago dog.
A true Chicago-style hot dog is a culinary masterpiece built on a very strict set of rules.
It starts with an all-beef Vienna frankfurter on a poppy seed bun.
Then, it is “dragged through the garden,” meaning it is topped with yellow mustard, neon green sweet relish, chopped onions, tomato slices, a pickle spear, sport peppers, and a dash of celery salt.
But the most important rule of all? Absolutely no ketchup.
If you ask for ketchup at a classic stand, you will be publicly shamed (there is actually a real historical reason Chicago banned ketchup!).
Want to find the perfect bite? Check out our guide to the best hot dogs in Chicago according to locals.
- 📍 Where to find it: Gene & Jude’s, The Wieners Circle, or Portillo’s.
- 💡 Local Tip: If you absolutely must have ketchup for your fries, ask for it quietly.
4. Marvel at the World’s Largest Permanent Digital Art Projection
Chicago doesn’t just put art in museums; it projects it onto the city itself.
Art on theMART is a massive, permanent digital art projection.
It takes up 2.5 acres of the river-facing façade of the Merchandise Mart building.
Every night from spring through fall, you can stand on the Chicago Riverwalk and watch this mesmerizing, larger-than-life light show.
It is completely free to the public and features works from renowned contemporary artists.
- 📍 Where to find it: The Chicago Riverwalk, between Wells and Lake St.
- 💡 Local Tip: Grab dinner at one of Chicago’s best restaurants with a view before heading down to the riverwalk to watch the show!
5. Explore a Captured WWII U-Boat… Indoors!
The Museum of Science and Industry (MSI) in Chicago is mind-blowing, but one exhibit stands completely alone.
Deep inside the museum, you will find the U-505.
This is an actual German submarine that was captured by the U.S. Navy during World War II.
It is the only German U-boat in the United States, and many employees swear the U-505 submarine is haunted.
Even more incredibly, they built a massive underground bunker around the submarine so you can tour the inside of it year-round.
Walking through the cramped, historic quarters of a real WWII enemy vessel in the middle of the American Midwest is a surreal experience.
- 📍 Where to find it: Museum of Science and Industry (Hyde Park).
- 💡 Local Tip: The onboard tour requires an extra ticket, so buy it online in advance before they sell out.
6. Touch the Ivy at Wrigley Field
Baseball fans know that there is no stadium quite like Wrigley Field.
Built in 1914, it is the second-oldest ballpark in the major leagues.
But what makes it truly one-of-a-kind is the outfield wall.
Wrigley Field is the only professional baseball stadium in the world with an outfield wall covered entirely in Boston ivy.
Watching a summer game while the ivy is bright green is a bucket-list experience for any sports fan.
If a baseball gets lost in the ivy during a game, it’s an automatic ground-rule double!
- 📍 Where to find it: Wrigley Field (Lakeview/Wrigleyville).
- 💡 Local Tip: The ivy doesn’t turn green until late May or early June, so plan a mid-summer visit for the best photos.
7. Cruise a River That Flows Backwards
Yes, you read that right. The Chicago River flows backwards.
In the late 19th century, Chicago pulled off one of the greatest engineering feats in human history.
To stop pollution from flowing into Lake Michigan (the city’s drinking water supply), engineers reversed the flow of the Chicago River.
Today, the river flows away from the lake and towards the Mississippi River basin.
Taking one of the highly-rated architecture boat tours on a reversed river is an experience exclusive to Chicago.
And if you visit on St. Patrick’s Day? You get to see this backwards-flowing river dyed a brilliant, vibrant emerald green!
- 📍 Where to find it: The Chicago River (Downtown).
- 💡 Local Tip: The absolute best way to experience this is on an architecture boat tour at twilight.
8. Play a Game of 16-Inch “No-Glove” Softball
If you go to a park in Chicago during the summer, you might see a baseball game that looks a little… wrong.
That is because Chicagoans play a highly specific, localized sport called 16-inch softball.
Locals affectionately call it “mushball” or “Chicago ball” (just one of many unique Chicago slang terms you’ll hear around town).
The softball is massive—16 inches in circumference—and it gets softer as the game goes on.
Because the ball is so big and squishy, players do not wear baseball mitts.
Catching a line drive barehanded is a badge of honor here, and you won’t find this sport played seriously anywhere else on the planet.
- 📍 Where to find it: Grant Park, Oz Park, or any local neighborhood park in summer.
- 💡 Local Tip: Grab a blanket, some snacks, and just watch the locals play—it gets highly competitive!
9. Eat an Authentic Humboldt Park Jibarito
Chicago’s food scene goes way beyond deep-dish pizza and hot dogs.
If you want a true, born-in-Chicago culinary exclusive, you have to eat a Jibarito.
Invented in the 1990s in Chicago’s Humboldt Park neighborhood by Puerto Rican immigrants, this sandwich is a masterpiece.
Instead of using bread, a Jibarito uses two flattened, fried green plantains.
It is typically stuffed with steak, cheese, lettuce, tomato, and a heavy smear of garlic mayonnaise.
It is crispy, savory, and a uniquely Chicago-Rican invention that you simply have to taste to believe.
- 📍 Where to find it: Papa’s Cache Sabroso or Jibaritos y Más (Humboldt Park / Logan Square).
- 💡 Local Tip: Order it with a side of arroz con gandules (Puerto Rican rice with pigeon peas).
10. Get Lost in the Underground “Pedway”
Chicago winters are notoriously brutal, but locals have a secret weapon.
The Chicago Pedway is a massive, 40-block network of underground tunnels and overhead bridges.
It connects skyscrapers, train stations, and some of the most stunning free hotel lobbies in Chicago right in the heart of the Loop.
You can literally walk for miles across downtown Chicago without ever stepping foot outside.
The Pedway is a bizarre, fascinating mix of sleek corporate hallways, hidden coffee shops, and slightly creepy, neon-lit corridors.
Taking a walking tour of this subterranean maze feels like exploring a secret city beneath the city.
- 📍 Where to find it: Entrances are scattered throughout the Loop (look for the black and yellow compass signs).
- 💡 Local Tip: Download a Pedway map on your phone before you go; it is very easy to get turned around!
11. Order an Italian Beef “Dipped” (With Giardiniera)
Thanks to the hit TV show The Bear, the world now knows about the Chicago Italian Beef sandwich.
But eating one in its birthplace is a completely different experience.
This isn’t just a roast beef sandwich; it is a messy, glorious, structural marvel.
Thinly sliced, highly seasoned roast beef is piled onto a French roll, but the magic is in the ordering process.
You have to order it “dipped,” meaning the sandwich maker takes the entire thing with tongs and dunks it completely underwater in the beef juices (au jus).
Top it with spicy, oil-based Chicago giardiniera and adopt the “Chicago Lean” stance so you don’t ruin your shoes!
Ready to try one? Here is our definitive list of the absolute best Italian beefs in Chicago.
- 📍 Where to find it: Al’s Beef, Johnnie’s Beef, or Mr. Beef.
- 💡 Local Tip: Ask for it “juicy” or “dipped” and always add hot giardiniera for the true local experience.
12. Stand at the Exact Starting Point of Route 66
Route 66 is the most famous highway in American history.
Known as the “Mother Road,” it stretches all the way to Santa Monica, California.
But every epic road trip has to start somewhere, and that somewhere is exclusively in Chicago.
Right on Adams Street in downtown Chicago, you will find the iconic, brown “Begin Route 66” sign.
Snapping a photo under this sign is a bucket-list moment for travelers from all over the globe.
You can only begin the ultimate American road trip right here in the Windy City.
- 📍 Where to find it: East Adams Street at South Michigan Avenue.
- 💡 Local Tip: Look up! The sign is mounted high on a light pole, making it easy to walk right past if you aren’t paying attention.
13. Visit the Only Bahá’í Temple in North America
Okay, this one is technically just north of the city limits in Wilmette, but it is a must-do Chicago-area exclusive.
There are only a handful of Bahá’í Houses of Worship in the entire world.
The one sitting on the shores of Lake Michigan is the only one in North America, and the oldest surviving one on earth.
The architecture is absolutely jaw-dropping, easily rivaling the most beautiful historic churches in Chicago.
It features a massive, lace-like dome surrounded by stunning, perfectly manicured gardens.
It is completely free to enter, incredibly peaceful, and offers a spiritual and architectural experience you literally cannot find anywhere else on the continent.
- 📍 Where to find it: 100 Linden Ave, Wilmette, IL.
- 💡 Local Tip: Take the CTA Purple Line to the Linden stop; it’s a short, beautiful walk through a historic neighborhood from there.
14. Eat the Original 1893 Brownie at the Palmer House
Did you know the brownie was invented in Chicago?
During the 1893 World’s Columbian Exposition, Bertha Palmer needed a dessert that could fit in a boxed lunch for the Women’s Pavilion.
She asked the pastry chefs at her hotel, the Palmer House, to create a cake-like confection that was easy to eat.
The result was the world’s very first brownie, made with walnuts and an apricot glaze.
The best part? The Palmer House Hilton is still open today and is consistently ranked as one of the best downtown Chicago hotels.
You can walk right into their stunning, historic lobby and order the exact same brownie recipe that started it all over 130 years ago!
- 📍 Where to find it: Palmer House Hilton (Downtown Loop).
- 💡 Local Tip: You don’t need to be a hotel guest to order one at the lobby bar.
15. Sit in Al Capone’s Favorite Booth at The Green Mill
Chicago’s Prohibition-era gangster history is legendary, but much of it has been paved over.
However, at The Green Mill Cocktail Lounge in the Uptown neighborhood, time has stood still.
This historic jazz club was partly owned by “Machine Gun” Jack McGurn, a top associate of Al Capone.
Capone was a regular here, and you can actually sit in his favorite booth (the one with clear views of both the front and back doors).
There is even a trap door behind the bar that leads to a network of underground tunnels used to smuggle booze and escape the police.
Sipping a classic cocktail while listening to live jazz in Capone’s actual hangout is an unmatched, gritty Chicago experience. (If you love this era, you should also check out our guide to Chicago’s best hidden speakeasies!).
- 📍 Where to find it: 4802 N Broadway (Uptown).
- 💡 Local Tip: Bring cash! This historic spot does not accept credit cards.
16. Meet SUE, the World’s Most Famous T. Rex
Lots of cities have natural history museums, but only Chicago has SUE.
Housed inside the incredible Field Museum, SUE is the most complete, best-preserved, and one of the largest Tyrannosaurus rex skeletons ever discovered.
Standing 13 feet tall at the hip and 40 feet long, this fossil is a global treasure.
The museum even built SUE their very own private suite, complete with atmospheric lighting and a narrated light show that highlights the dinosaur’s battle scars.
Standing face-to-face with this apex predator is a humbling experience you can only get on Chicago’s Museum Campus.
- 📍 Where to find it: The Field Museum (Museum Campus).
- 💡 Local Tip: Don’t miss the 20-minute light and sound show in SUE’s private suite.
17. Eat Deep Dish with a “Caramelized Halo” at Pequod’s
We couldn’t finish a Chicago list without mentioning deep-dish pizza.
While you can get generic deep dish shipped across the country now, there is one specific pie you must eat on-site.
Locals will fiercely debate the best pizza, but Pequod’s Pizza in Lincoln Park offers something totally unique.
Instead of a traditional crust, Pequod’s lines their cast-iron pans with mozzarella cheese before baking.
This creates a dark, chewy, caramelized “halo” of crispy cheese around the entire edge of the pizza.
It is a textural masterpiece that ruins all other pizzas for you, and it is a strictly Chicago obsession. (Curious who else made the cut? Read our local debate on the best deep dish pizza in Chicago).
- 📍 Where to find it: 2207 N Clybourn Ave (Lincoln Park).
- 💡 Local Tip: Wait times can exceed two hours on weekends, so make a reservation well in advance.
18. Eat the Real Chicago Pizza: Tavern-Style
While deep dish gets all the tourist glory, true Chicagoans know that Tavern-Style Pizza is the actual pizza of the city.
Born in the neighborhood taverns of the South Side, this pizza features a cracker-thin, crispy crust.
It is always cut into small squares (never triangles) so it can be easily eaten with one hand while holding a beer in the other.
You simply cannot get authentic, perfectly crispy tavern-style pizza outside the Midwest.
Eating a square-cut pie in a wood-paneled neighborhood joint is as authentic as Chicago gets.
- 📍 Where to find it: Vito & Nick’s, Pat’s Pizza, or Barnaby’s.
- 💡 Local Tip: The corner pieces (the tiny triangles with no crust edge) are the most highly coveted slices!
19. Witness the “Chicagohenge” Phenomenon
Because Chicago was built on a strict grid system, it creates a stunning natural phenomenon twice a year.
During the spring and autumn equinoxes, the sun aligns perfectly with the city’s east-west streets.
This creates a breathtaking visual where the sun sits exactly between the towering skyscrapers of the Loop, casting a golden glow down the concrete canyons.
Photographers and locals line up in the streets to capture this incredible alignment.
It is a beautiful marriage of nature and urban planning that you can only witness here. (Check out our guide on where to see the Chicagohenge sunset!).
- 📍 Where to find it: Any east-west street in the Loop (Washington, Madison, and Monroe are best).
- 💡 Local Tip: This only happens in late March and late September, so time your trip accordingly!
Final Thoughts on Unique Chicago Experiences
Chicago is a city that proudly marches to the beat of its own drum.
From terrifying glass ledges to bizarrely bitter liquors, the Windy City offers memories you can’t make anywhere else.
Next time you visit, skip the generic tourist traps and embrace the weird, the wonderful, and the uniquely Chicago experiences that make this city so special.
Before you pack your bags, make sure to read our essential guide: Is Chicago actually safe for tourists? (Spoiler: Yes, as long as you follow a few local rules!).
Have you ever done any of these unique Chicago activities?
Did you survive the Malört face? Let me know in the comments below!