Unique Things to Do in Chicago: Hidden Gems & Unusual Adventures
Are you ready to discover a side of Chicago that few have had the courage (or maybe just the insider info) to explore? Fasten your seatbelts, folks. It’s going to be a bumpy ride!
Ever thought to yourself, “I wonder what unusual things I can do in the Windy City this weekend?” If so, you’re in luck! This guide is packed full of the weird, wonderful, and downright strange places and unique things to do in Chicago that might not find their way onto every tourist’s checklist. If you’re a local, you might even discover a hidden gem right in your own backyard – ain’t that a shocker?
From cutting-edge theaters and avant-garde museums that defy traditional norms to spine-tingling crime tours that might just have you clutching your pearls, Chicago certainly hosts more than just the Magnificent Mile, Navy Pier, and deep-dish pizza.
You’re about to plunge headlong into some of Chicago’s best kept secrets – off-the-beaten-path Chicago adventures, unique eateries, atypical shopping, and a whole lot more.
Chicago Off the Beaten Path: Unique Things to Do Chicago
The Neo-Futurists Chicago – 5153 N Ashland Ave, Chicago, IL 60640
Feeling adventurous and ready to immerse yourself in something utterly unique in Chicago? Look no further than the Neo-Futurists, a collective of wildly creative and daring performance artists who deliver a form of theatre nonpareil.
Tucked in an unassuming theatre in Andersonville, their signature late-night event, “The Infinite Wrench,” offers 30 plays in 60 minutes.
The Neo-Futurist aesthetic calls for the performers to play themselves in an “ongoing, real-time, autobiographical” manner. Each performance is a fresh blend of the comic, tragic, political, personal, and abstract. Never dull, always inventive, it’s a unique Chicago experience guaranteed to spark an endless carousel of emotions.
This isn’t your typical sit-down theatre event – audience participation is the name of the game and the reason why it has been dubbed one of the most unusual things to do in Chicago. You’re not just an observer at the Neo-Futurists; you’re an active participant in a rapidly unfolding series of micro-plays.
So, if you’re up for some stimulating, visceral, and unique experiences Chicago offers, you’d better mark your calendar for “The Infinite Wrench” (and maybe bring a friend or three!).
Museum of Surgical Science – 1524 N Lake Shore Dr, Chicago, IL 60610
Ever wondered where the heart of surgery began, or what practices were once considered cutting-edge? Wax figures, skeletons, and other somewhat creepy displays are all here to give you a truly unique Chicago experience. Strap in for a wild ride into the world of medicine at the Museum of Surgical Science!
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Located in an exquisite mansion overlooking Lake Michigan, this museum holds an extensive collection of fascinating – and occasionally grisly – artifacts from the history of surgery.
Get ready to go goggle-eyed over a vast array of historical medical equipment, stunning stained-glass windows, and old surgical manuals that will surely give you the chills (ever seen a trepanation?).
Not enough to satisfy your intriguingly weird thirst for knowledge? The place is brimming with photographic exhibits and interactive displays covering a range of topics from ancient surgical techniques to modern medical breakthroughs. You’ll find yourself immersed in the fascinating timeline of surgical science swiftly.
American Writers Museum – 180 North Michigan Ave, Chicago, IL 60601
Ever thought about what it’d be like to dive headfirst into the mind of your favorite American writer? Yep, you guessed it right! The American Writers Museum is just the place to do that. Located at the heart of Chicago, this little gem offers a unique Chicago experience you seldom get elsewhere.
Unlike other museums, it doesn’t drowsily shove facts down your throat. As a top contender in our list of Chicago unique things to do, it invites you to engage in interactive exhibitions that take you on a remarkable journey through the history of American literature.
You’ll get a chance to feel like you’re having a one-on-one with Hemingway or stepping into the poetic universe of Maya Angelou. Sounds exciting, doesn’t it?
And the best part? They’re open seven days a week! So, whether you’re looking for unique things to do in Chicago this weekend, or just want to add this to your crazy things to do in Chicago list, it’s always a good time to visit!
Join Night Crime Tours
Ever intrigued by the dark side of history? Got a thing for true crime? We’ve got something that perfectly matches your unique interests. Time to step out of the ordinary and explore Chicago’s eerie past with Night Crime Tours. Hold on tight, ’cause this is not your run-of-the-mill sightseeing tour!
These realistic and adrenaline-filled tours lead you through some of the city’s most notorious places, where chilling incidents and high-profile crimes take place. Talk about a truly unique Chicago experience!
Hankering for the spooky ambiance of an old-time crime scene? They’ve got you! The guide, an expert in crime history, pulls you right into the narratives with their vivid storytelling.
You’ll get to visit the actual locations and feel the echoes of the past bouncing off the walls. Grisly business, right? The tours usually run for a couple of hours, so gear up for a thrilling night adventure in unique places in Chicago.
And remember, what happens in the crime tour… gets tweeted, texted, and Instagrammed. After all, you’re going to want to share this wild experience!
Bad Axe Throwing Chicago – 165 N Loomis St, Chicago, IL 60607
Thinking of unique things to do in Chicago? How about embracing your inner Viking while exploring the Windy City? Yep, you read that right! Welcome to Bad Axe Throwing Chicago, a unique Chicago experience for adrenaline junkies and history buffs alike. Not your average Saturday night out, is it?
Located in the heart of the city, this is a safe, exciting, and – let’s be candid – slightly bizarre way to spend your time exploring unique Chicago. Whether you’re an axe-throwing newbie or a seasoned pro, the friendly crew here is ready to guide you in the fine art of hurling a hatchet (and making sure you don’t injure anyone in the process!).
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Fancy a bit of friendly competition? Why not challenge your friends to a game? And don’t worry if you’ve never held an axe before. The skilled team members are on hand to offer one-to-one tuition, ensuring you quickly get the hang of this ancient sport.
The atmosphere is energizing, fostering a unique go-getter spirit. It’s not every day you get the chance to sling an axe in the middle of a major city! By diving headfirst into such an off-the-beaten-path Chicago experience, you’re sure to remember your trip to the quirky and unforgettable Windy City!
Bonus fun fact for you: Did you know that Bad Axe Throwing also offers knife throwing? Now there’s an unusual adventure to add to your ‘weird things to do in Chicago’ list!
TILT 360 Chicago – 875 N Michigan Ave 94th floor, Chicago, IL 60611
Ever dream of teetering 94 stories above The Magnificent Mile? Well, TILT 360 Chicago‘s got you covered. Get ready to add a dash of vertigo to your Unique Chicago Experience.
This one-of-a-kind attraction tilts you over the edge of the John Hancock Center, all while being securely harnessed, of course, for a whole new perspective on the Windy City.
Pretty cool, huh? But let’s clear up any heart palpitations you might be experiencing – the experience is completely safe. Your safety’s their number one priority, right after ensuring you have an adrenaline-rushed good time.
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Just a word of caution: maybe avoid this one if you have a fear of heights. Or go for it, if you’re looking for unique things to do in Chicago this weekend to get your heart racing! Go on, give this crazy thing to do in Chicago a tilt and make your Insta-followers green with envy.
Big Joe’s Turtle Races – 1818 W Foster Ave, Chicago, IL 60640
What’s the one thing less predictable than Chicago’s weather? The outcome of Big Joe’s Turtle Races, of course! This is the zany, off-the-wall Friday night activity you didn’t know you needed in your life.
Yes, you read that right. At Big Joe’s, a dive bar like no other in the heart of Chi-town, you can enjoy your frosty pint of beer with a side of… turtle racing. Is there any other unique Chicago experience that screams ‘weirdest Friday night out’? We doubt it!
So how does it work? It’s quite simple. Turtles are placed at the center of a circular table, and the first one who reaches the edge wins the race. You can’t make this up, folks.
If you’re named the lucky ‘handler’ you even get to pick the speedy (or not so speedy) turtle you hope to pin your victory on. Talk about an extraordinary thing to do in Chicago! It’s all in good fun (and strictly no wagering!).
Expect buckets of laughter, friendly banter, and a whole lot of turtle puns. There’s something oddly infectious about cheering on a tipsy turtle named ‘Fast Eddie’.
Or watching ‘Slowpoke Rodriguez’ live up to its name. All while you’re nursing a drink and some great Chicago-style bar snacks. If unique experiences in Chicago are on your bucket list – don’t walk, but race to Big Joe’s!
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House of the Temple Chicago – 907 Monroe St, Dearborn, MI 48124
If you have a knack for finding unique things to do in Chicago, the House of the Temple should be at the top of your list. Nope, we’re not talking about the usual trip to the Cloud Gate or a stroll around the Navy Pier. We’re referring to genuinely unique Chicago experiences, the ones that take you off the beaten path, the kind that you’d be buzzing about to your friends back home.
So, what’s so special about the House of the Temple? Well, this place isn’t just any old building. It’s one of the oldest historical buildings in the city, originally erected back in 1923. This brick-and-mortar marvel was initially home to the Humboldt Park Commandery No.79, tied with the Freemasons.
This Masonic Lodge on Dearborn offers public tours filled with symbolism, mysterious artifacts, and hidden meanings. Yes, you’ve hit the jackpot for unique places in Chicago!
The House of the Temple is a testament to craftsmanship with years of history etched into its foundation. If those walls could talk, oh, the stories they’d tell! So, why not head there this weekend, and give these silent storytellers a patient ear? You’re in for the ride of your life with this history-steeped unique Chicago experience. How about that for some Chicago off the beaten path flair?
Woolly Mammoth Antiques and Oddities – 1513 W Foster Ave, Chicago, IL 60640
Have you ever wanted to… browse a collection of WWII gas masks while casually trying on a vintage polka-dotted corset? Or maybe you’re just in the market for some antique medical equipment?
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Look no further than the wonderfully unique Chicago hotspot, Woolly Mammoth Antiques and Oddities. With its dangerously delightful assortment of curiosities, it’s a unique experience Chicago proudly features on its roster of extraordinary cool experiences.
It’s a mad hatter’s paradise, so prepare to spend quite a bit of time in this fascinating and unusual thrift store (for those searching for unique thrift store Chicago).
Beyond quirky keepsakes, Woolly Mammoth also showcases an impressive array of taxidermy. From claw-footed ottomans to spectacular birds in mid-flight, there are enough stuffed curios to make a Victorian swoon. Want to bring home something a bit zanier? Well, you might just find the perfect mummified rodent or a carnivorous plant.
If you’re wondering, “Is this weird?” the answer is yes, yes it is. But that’s part of the appeal. Because nothing says “unique things to do in Chicago” quite like strolling out of a store with a vintage accordion and the amount of a two-headed duckling.
So, why not take a deep breath and dive into the wonderfully weird world of Woolly Mammoth Antiques and Oddities?
Unique Chicago FAQs
Are There Any Weird Things to Do in Chicago?
Oh, weird you say? Absolutely! You can immerse yourself in a swirling illusion at the Museum of Illusions, hunt for oddities and unique treasures at stores like the Woolly Mammoth Antiques, or embark on a thrilling self-planned scavenger hunt around the city, just to add a twist of peculiar to your unique Chicago experience!
Are There Any Cool Experiences in Chicago?
Oh, you bet there are! Why not embark on a self-planned scavenger hunt across the city's hidden gems, or test your adrenaline with a daring visit to TILT 360 Chicago?
And of course, no 'cool experience' list would be complete without mentioning Chicago's array of spectacular rooftop bars - imagine sipping a cocktail at unique bars in Chicago with the windy city skyline as your backdrop!
Get Discount Tickets to the Weirdest Places in Chicago
Ready to dive into some of Chicago’s weirdest places could give? Well, we got you covered! You’ve read about all these oddities, now it’s time to see them for yourself. Don’t worry about the price tag, you can score discount tickets on Tripster. Why not give it a whirl? After all, a little peculiarity never hurt anyone, right?
And if you’re looking for unique hotels in Chicago, check out interesting stays here. You can bundle accommodations with discount tickets too!
Go on, book that tour now, and let the unique Chicago experience begin!
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