19 Unique Things to Do in Chicago for Roadside Attraction Lovers

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If you’re hunting for unique things to do in Chicago, you’re my kind of traveler.  I’ve spent plenty of time in the Windy City since it’s just a couple of hours from home, and every visit teaches me something new.  Sure, I’ve enjoyed the classic tourist attractions.  I’ve taken a selfie at The Bean, snapped photos in front of Buckingham Fountain in Grant Park, and even wandered Navy Pier with a Diet Coke in hand.  But if you know me, you know I can’t resist a good roadside oddity.

So, in between the big attractions, I’ve tracked down some wonderfully weird and whimsical stops that show off Chicago’s quirky personality.  These spots are perfect for a day trip, a solo adventure, or a detour between museums and shopping sprees on the Magnificent Mile.

Grab your comfy walking shoes and a sense of humor, because we’re about to explore 19 of the best places that prove Chicago isn’t just about skyscrapers and style.  It’s got plenty of charm hiding in plain sight.  And if you’re like me and love jotting down your adventures, grab my Free Printable Travel Journal to keep track of your favorite discoveries and the ones you still need to visit next time.

If you’re road-tripping beyond Chicago, don’t miss my complete guide to Illinois Roadside Attractions. And check Choose Chicago for calendars, maps, and free events before you go.

Unique Things to Do in Chicago: The City’s Quirky Heart

There’s no shortage of skyscrapers and selfies in downtown Chicago, but the city’s real personality shows up in the odd corners.  Between bites of deep dish pizza and strolls along the Chicago Riverwalk, I like to wander off the well-worn tourist trail and find the kind of stops that make you smile, scratch your head, or both.  These are the unique things to do in Chicago that prove the Windy City knows how to have a little fun with itself.

Chicago’s Downtown Oddities and Iconic Weirdness

From shiny sculptures to million-dollar displays, downtown Chicago has no shortage of delightful weirdness.

The Bean (Cloud Gate)
It’s shiny, selfie-perfect, and somehow still surprising every time you see it.  Take a moment to watch people watching themselves.  Let’s be honest, that’s the real show. And this is the perfect reason to upgrade your own selfie game with a few of my very own selfie tips.

📍 Located at Millennium Park, 201 E. Randolph St., Chicago, IL

Crown Fountain
Two giant faces in Millennium Park spit water on passersby, proving that art can also be a splash zone. My favorite part is waiting for the images to change faces.

📍Located at Millennium Park at 201 E. Randolph St., Chicago, IL, between Michigan Ave. and Columbus Ave. 

Famous Rocks of the Tribune Tower
From the Great Wall of China to the moon, this landmark building has stones embedded from around the world.  My personal favorite is the piece of twisted wreckage from the Twin Towers, showing that not all history is ancient.

📍Located on the East side of the Tribune Tower at 435 North Michigan Avenue in Chicago, IL

Robin Williams Mural
Tucked in the Logan Square neighborhood, this vibrant mural blends Robin with his unforgettable Genie from Aladdin.  His eyes in this mural are haunting.  And the colors pop.

📍Located at 2051 N. Milwaukee Ave, Chicago, IL

Vertical Map of the Chicago River
A skyscraper-sized map on the side of this building, facing the Chicago River, turns the Chicago River into public art.  The best way to get a view is on the Architectural boat tour.

📍Located on the West side of the building at 300 S. Wacker Drive, Chicago, Il

Begin Route 66 Sign
Snap your photo and start dreaming of open roads, classic diners, and fun attractions all the way to California. Keep an eye out for the “end of Route 66” sign one block south. I haven’t found it, but it’s on my list! Cruising Route 66? Keep rolling through Joliet and beyond with my Central Illinois roadside list.

📍Located on E. Adams St, just West of the S. Michigan intersection in Chicago, Il

If you’re a fan of Route 66, take a look at 10 Quirky Muffler Men Statues That Will Make You Pull Over.

Starbucks Reserve Roastery
Coffee lovers, prepare to swoon.  This five-story Michigan Avenue temple to caffeine is the world’s largest Starbucks. It serves as both a café and an amusement park for grown-ups who run on lattes.

📍Located at 646 North Michigan Avenue, Chicago, IL

McDonald’s Global Menu Restaurant
This unique McDonald’s lets you taste menu items from around the world.  One bite of Japan’s teriyaki burger or Canada’s poutine, and you’ll forget you’re sitting in the middle of downtown Chicago. I love that you can order from the digital menu, just like an ordinary McDonalds.

📍Located at 1035 W. Randolph Street, Chicago, IL

Tilt:  103rd Floor Experience
Step in and tilt out over the city on the 94th floor of the 360 Chicago Observation Deck (formerly known as the John Hancock Center).  Just be sure to hang on tight.  I’m terrified of heights, but I found this a safe way to test my limits, even in the tallest building in the city. But don’t confuse this with the Skydeck, an observation deck on the 103rd floor of the Willis Tower, which features an attraction called The Ledge. Both are thrilling and uniquely Chicago!

📍 Located on the 94th floor of 360 CHICAGO Observation Deck, 875 N. Michigan Ave. (Skydeck with The Ledge is at Willis Tower.)

Unique Things to Do in Chicago – Quirky Suburban Finds

If you’ve already checked off the big names downtown, it’s time to head for the suburbs.  Within an hour of the Chicago Loop, you’ll find giant cows, smiling water towers, and even a giraffe peeking through a roof.  These unique things to do in Chicago are all close enough for an easy day trip, but weird enough to make you glad you ventured out.

Western Suburbs of Chicago

Once I get my fill of skyscrapers and selfies downtown, it’s time to trade city streets for those suburban tree-lined neighborhoods and a slower pace. The western suburbs are full of charm, character, and just the right amount of weird. From storybook homes to Seussian statues, you’ll find that Chicago’s sense of humor stretches well beyond the Loop. Ready to keep exploring? Head just a bit farther for more roadside fun in Northern Illinois.

Green Eggs & Ham Statue – Naperville
A delightful nod to Dr. Seuss that proves you’re never too old for a good rhyme or a silly photo.

📍Located at the 95th Street Public Library at 3015 Cedar Glade Dr., Naperville, Il

Sears Catalog Home Capital of the World – Downers Grove
Take a stroll past century-old houses ordered right from the Sears catalog, back when “add to cart” meant filling out a paper form.

📍Find these homes sprinkled all around the Downers Grove area.

Radio Flyer Wagon – Elmwood Park
A bright red reminder of childhood. At 27 feet, that’s big enough for more than one grown-up to climb aboard (or at least try).

📍Located at the Radio Flyer Factory at 6515 W. Grand Ave, Elmwood Park, Il

If giant stuff is your jam, you’ll love Casey Illinois Attractions: The Little Town with the World’s Biggest Things

Giraffe Through Roof – Aurora
Yes, a giraffe is popping out of a building, and no, it’s not an illusion.  Bring your camera and your sense of humor to this local dentist’s office.

📍Find this happy guy at Grand Dental at 1780 N. Farnsworth ave, Aurora, Il

Southern and Southwestern Suburbs

Blues Brothers and Bluesmobile – Woodridge
Jake and Elwood are dancing atop this kitschy ice cream shop. Go ahead and bust a move with them. You know you want to.

📍Find them at Rich and Creamy at 920 N. Broadway St., Joliet, Il

Giant Black and White Cow – Mokena
This larger-than-life queen of dairy is a great spot for a quick selfie.  And be sure to grab an ice cream treat at The Creamery after your selfie.

📍Located at The Creamery at 19000 Wolf Rd, Mokena, Il

The Largest Collection of Richard Haas Murals – Homewood
Don’t let your eyes fool you with these walls that look like buildings and buildings that look like walls.  These 3D illusions will confuse even the most discerning eye.

📍Find these murals all around town in Homewood, IL

Smiley Face Water Tower – Calumet City
She’s been beaming down at drivers for decades, proving happiness really does come in industrial-sized packages.

📍Located behind Calumet City Animal Control at 1651 Dolton Rd., IL

Scale Model Smiley Water Tower – Calumet City
Because one smile wasn’t enough, there’s a mini version too.  Double the grin, double the photo ops.

📍Located at the Intersection of Sibley Blvd and Crandon Ave in Calumet City, IL

A Mobster’s Resting Place

Grave of Al Capone – Hillside
Step quietly among the headstones and you’ll find the infamous gangster’s final resting place.  Wear comfy walking shoes (I LOVE these Skechers Slip-ins), ‘cuz cemeteries aren’t made for stilettos, no matter how hip you are.

📍Located in Mount Carmel Cemetery at 1400 S Wolf Rd, Hillside, IL

The Quirky Chicago Museums You’ll Love

Chicago isn’t short on world-class museums like the Museum of Science and Shedd Aquarium, but if you’re anything like me, you love the spots that make you grin while you learn.  These museums are less about velvet ropes and more about playful discovery.  They are the kind of places where you can take pictures, eat ice cream, and maybe learn something new about an old favorite.

Ice Cream Museum
This bright pink paradise was the perfect place for me.  I joke that it was perfect Hip Grandma camouflage.  And I loved frolicking along with a group of gifted students who were in Chicago for a conference but enjoyed a day of play before their hard work.  The Chicago Museum of Ice Cream was the perfect treat for them.  And the best part?  There are ice cream tastings around every corner.  You won’t leave hungry!

📍Located at 435 N. Michigan Ave., Chicago, IL

Cube of $1 Million at the Federal Reserve Bank
One of the best things here is that the Money Museum in the Federal Reserve Bank of Chicago offers free admission!  And you even get escorted in by a snappily dressed security guard once you’re in the front door of this historic building.  But it’s only part of the fun.  Once you’re in, you can stand beside this sparkling stack of cash and imagine your next great trip.  Bonus: no spending required.

📍Located at 230 S LaSalle St, Chicago, IL

Plan Your Chicago Adventure Like a Pro

Whether you’re a first-time visitor or a lifelong resident, exploring these unique things to do in Chicago is a great way to see a lighter, quirkier side of the city.  Visit between spring and fall for free events, live music, and plenty of sunshine for your photo ops.  The summer months are the best time to get outside and wander.  Winter can be bitterly cold in the Windy City.  After your roadside adventures, you can’t go wrong with a stroll along the Chicago Riverwalk, a spin on the Navy Pier Ferris wheel overlooking Lake Michigan, or a peek inside the Art Institute of Chicago or the Chicago Botanic Garden.

Grab yourself a Ventra Card for easy rides on the CTA buses and ‘L’ trains.  It’s the simplest way to zip around town like a local.  Round out your trip with a few Chicago favorites, like the Field Museum, Shedd Aquarium, and Adler Planetarium, which are all worth the time.  And when the day winds down, grab a seat at a rooftop bar overlooking Michigan Avenue and toast to your next adventure. If you’re heading further south on your road trip, bookmark my Southern Illinois roadside guide for a whole list of fun downstate!

A Note About Safety in the City

Chicago is a fantastic city to wander solo, but don’t get so caught up in all the best things to do that you forget a few basic safety tips. A cross-body phone strap can save your phone (and your heart rate) if it tries to go flying off Michigan Avenue.

Carry a small crossbody bag (I love this one from Baggallini) to keep your essentials close and your hands free. This style keeps your valuables in sight and is harder for pickpockets to reach than an over-the-shoulder bag or backpack.

I’ve always felt comfortable exploring Chicago during the day, especially in well-populated areas. Trust your instincts, stay aware of your surroundings, and don’t hesitate to ask for help — locals are proud of their city and happy to point you in the right direction. Just ask the kind young man who once helped me navigate the bus system to the Federal Reserve! And if solo travel makes you nervous, here’s how I handle the jitters and still go.

A few more simple safety musts:

• Keep a portable phone charger handy so you never lose navigation or access to rideshares.
• Use crosswalks and pay attention to signals, especially downtown, where traffic moves fast and tourists move slow.

After all, the Chicago CityPASS is one of the best ways to see top attractions like the Shedd Aquarium and Field Museum while saving a little money and skipping a few lines.

Need a Place to Stay?

Finding a cozy spot to rest your feet after a long day of exploring is half the fun.  Use the map below to find hotels, B&Bs, or quirky stays close to your favorite attractions, from the Magnificent Mile to the Chicago Loop.

Wrap-Up: Keep It Quirky, My Friends

Chicago is packed with top-notch restaurants and landmark buildings, making it a world-class destination. But for me, it’s the under-rated fun found in quiet corners that make it unforgettable. Whether you’re hunting for a giant cow, sipping coffee at a world-famous Roastery, tasting something international at McDonald’s, or standing at the start of Route 66, remember that travel is about finding joy in the unexpected.

If you’ve discovered a treasure in the city that I missed, I’d love to hear about it.  Join me and thousands of others who love this kind of fun in the Quirky Roadside USA Facebook Group.  And before you hit the road, grab your Free Printable Travel Journal to jot down your favorite finds and a few you’ll save for next time.

PIN it for later!