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19 Unique Experiences in Chicago

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These are some of the most exciting & unique experiences in Chicago. They’re perfect activities for tourists visiting Chicago or locals looking to head off the beaten path in Chicago.

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19 Unique Experiences in Chicago

Let’s face it, most of our weekends probably look the same. Whether you’re staying in or dining out, hitting a bar or meeting for brunch… it gets old! You’ve clicked on this article, so we know you’re feelin’ it right now. 

This list is sure to spice up your Chicago routine. It may lead to one of the best experiences in Chicago that you’ve ever had! 

woman on Chicago bridge in downtown overlooking the river

19 Unique Experiences in Chicago

There are so many cool experiences in Chicago because it’s a big multicultural city. It’s the Midwest’s hub for dining, entertainment, arts & culture. No matter what you’re into, you’ll find some fun experiences in Chicago that suit your interests and budget.

'welcome to Chicago' sign

Our guide includes some conventional topics like unique shopping, unique museums, and unique dining experiences in Chicago. We’ve also included some of the unconventional experiences in Chicago that will surprise you. We’ve got the most fun stuff in Chicago of all sorts. 😉

1. Kayak on the Chicago River

You’ve probably kayaked on a lake or river somewhere. Boooooorrring!! One of the most adventurous things to do in Chicago is kayaking in the middle of downtown!

Yep, you can kayak on the Chicago River. This is one of the most fun outdoor things to do in Chicago. During your kayak experience, you’ll be privy to unparalleled views of the Chicago skyline. They’re the best views because you’re right in the middle of everything! 

In your kayak, you’ll float near the Chicago Riverwalk and view buildings from an eerie low angle. It feels like they’re towering over you — the scale is incredible! This is one of the cool things to see in Chicago. 

Book your Chicago kayak tour today.

No matter if you are looking for fun active things to do in Chicago with friends, or if you are looking to plan romantic dates in Chicago… book with Waterriders. 

Waterriders is one of Chicago’s most reputable kayaking companies. (We went with Waterriders in the photo displayed). Waterriders offers cool tours. They offer romantic sunset paddles, spooky ghost tours & seasonal fireworks experiences. 

2. Drive a Supercar

When you’re touring around the Chicago main attractions, you’ve probably seen a fancy sports car or too… especially if you’ve been hanging around the Gold Coast neighborhood. 

People watching and car gawking is definitely one of the relaxing things to do in Chicago. You might imagine yourself in one of these expensive vehicles shopping for clothes that cost an entire life’s savings. Ahhhh… dreamy, right?


Sign up for your supercar experience today.

Well, what if I told you that you could ride in one of these jaw-dropping cars. One of the best attractions near Chicago is the racetrack in Elmwood. For a small fee, you’ll be able to drive laps in a Ferrari, Lamborghini, Porsche, or McLaren! 

Usually, Elmwood doesn’t top the list of Chicago sites to see. Although, driving insanely high speeds in one of these luxury vehicles is one of the most interesting things to do in Chicago. 

3. See ariel views of the city

Chicago sightseeing on the ground is okay… but viewing the best places to visit in Chicago from above is legendary! Unlike some sketchy third world country that offers this tour, Helicopter rides in Chicago are very safe. 

Ariel view of chicago

Find out more about Chicago helicopter tours.

You can choose to do your helicopter tour during daylight, sunset, or nighttime. Many helicopter tours include a glass of champagne. So, this is one of the top things to do in Chicago for a special birthday, anniversary, or engagement. Just imagine the look on your friend, family member, or significant other’s face when you tell them that they’re about to see their favorite city from a completely different vantage point… a helicopter! 

This is also one of the best things to do in Chicago for photographers. If you love snapping cool and unique photos, if you own a DSLR, this activity is for you! These views are some of the one-in-a-lifetime things to see in Chicago. 

4. Explore Circus Arts

Do you enjoy dance, artistry, choreography, or love being active? Do you want to reconnect with your childlike self that enjoyed swinging on monkey bars? This next item on our list of wacky Chicago attractions is for you!

Chicago’s Trapeze School is one of the best places to visit in Chicago. It’s perfect for adults of all skill levels. No experience or training is required. Visitors can learn some basics of trapeze arts and get a sense of what it may feel like to train for Cirque Du Soleil. 😃

woman doing trapeze, gracefully falling onto trampoline

Try your skills at trapeze in Chicago. 

This trapeze school is very reputable in the acrobatics community, there are only 6 of its kind throughout the country. Also, this is one of the most fun things to do in Chicago!x

5. Make Mosaics & other interesting art

It’s cold in Chicago in winter…like… really, really cold. So, Chicagoans are always looking for fun indoor activities they can enjoy when winter mode takes over. Making mosaics isn’t one of the popular things to do in Chicago, but it is one of the best things to do in Chicago in December. 

The Chicago Mosaic School is a global leader in mosaic arts. It’s a non for profit institution that inspires creativity in both classical and abstract styles. 

mosaic art

Book this BYOB Mosaics class in Chicago.

The drop in BYOB class at the Chicago Mosaic School is one of the fun things for couples to do in Chicago. They’re also one of the fun things to do in Chicago in the rain, snow, or other inclement weather. 

6. Fly a plane

This next unique experience is for everyone who’s already seen all the top sights in Chicago. This is for locals who are looking for fun attractions in Chicago that aren’t touristy! 

What’s more unique than flying a plane? Yes, seriously, you can fly a plane!

small plane flying over blue sky

Sign up for an affordable introductory flight class. 

We’re only talking an introductory lesson here… but it’s certainly going to be an unforgettable experience. At the Avel Flight School, you can take off with an FAA-certified instructor. Choose from a 30 minute or 1-hour long flight. The course is very interactive and informative. It’s perfect for anyone interested in technology, electronics & machinery. 

P.S. This experience makes a great boyfriend gift. 

Although, planes aren’t the only fun gadgets that can soar over the fun places to visit in Chicago… consider flying a helicopter. Anyone who has already seen all the tourist sites in Chicago will love this!

Take a helicopter flying lesson at the Bachman Aero!

Learning to fly is one of the unique things to do in Chicago suburbs. 

7. Try your hand at leatherwork

This next activity is perfect if you’re looking for unconventional Chicago vacation ideas. 

Leatherwork isn’t usually considered one of the must see things in Chicago, but leatherwork has just as much history (or more) than some of the top places to visit in Chicago. 

preparations for leather work

Learn more about leatherwork classes in Chicago. 

Leather is one of mankind’s earliest important discoveries. Humans were utilitarian hunter-gatherers, and they used the hides of the animals they hunted to make clothing, footwear, and shelter. You can find leather work depicted in the Egyptian tombs and on ancient Greek urns. Leather is a part of our history as humans, and through leatherwork, we can experience what it may have been like to walk the earth hundreds of years ago.

The Chicago School of Shoemaking and Leather Arts is one of the top things to see in Chicago. They offer unique and fun classes where students can make boots, shoes, purses, and backpacks. You can also purchase a variety of handcrafted items.

Sign up for an introductory leatherwork class. 

8. Plunge into a Sensory Deprivation Tank

Some of the top attractions in Chicago are salons and spas. The Gold Coast and Old Town neighborhoods are some of the best places to go in Chicago for aesthetic and rejuvenating services. 

So, you’ve probably familiar with manicures, blowouts, and massages…but have you ever floated in a sensory deprivation tank? A sensory deprivation tank is a small pool that provides restricted environmental stimulation therapy (REST). 

woman 's face mostly submerged in water

Experience unparalleled relaxation in a sensory deprivation tank. 

Since you’re living in the modern world – you know how overwhelming it can be – phones buzzing, car horns, and construction in your building. This constant exposure to sounds and stimuli isn’t just annoying, it can be harmful to our neurological and psychological health. It prevents our brains and bodies from achieving a state of restful calm. 

hand resting on water

A sensory deprivation tank experience isn’t just one of the best nontouristy things to do in Chicago, it’s also a luxurious and rejuvenating experience that can improve your mental health. Sensory deprivation tanks can reduce anxiety, alleviate some symptoms of depression, and promote physical muscle relaxation.

VIVE Float Studio is one of the things to visit in Chicago that guarantees a healing and restorative experience. Bring your partner! This is also one of the best things for couples to do in Chicago. 

9. Learn how to make jewelry 

Ladies, you love jewelry, am I right? Have you ever thought about making your own? Jewelry making is a fun hobby that’s easy to pick up. It’s a great outlet for creativity, and it will awake your inner child. 

Jewelry making is also one of the inexpensive things to do in Chicago. But, even on a low budget, you can make cute and fashionable pieces that you’ll wear again and again. 

Learn how to make jewelry in Chicago.

jewelry making equipment, blue beads

Making jewelry is also one of the hipster things to do in Chicago. Handmade jewelry makes a great gift for a friend or relative, especially mom or grandma. 

Marilu Designs studio is one of the best places to visit near Chicago. It’s located in Arlington Heights, about 40 minutes’ drive outside downtown. 

Gallery’s Choice is another one of the interesting places in Chicago. Their guests can create unique glass pendants and other cool pieces. 

Create your own glass pendant. 

10. BYOB at a Bonsai Workshop

You may not realize that bonsai art is one of the most interesting things to do while in Chicago.

Bonsai art has been practiced in Asian cultures since the 10th Century. Miniature trees are still used to balance landscapes. Bonsai trees also have significance in the Zen Buddhist tradition.

Check out this awesome BYOB Bonsai class. 

Bonsai Tree

Consider an alternative BYOB Terrarium workshop.

Bonsai plants look beautiful in any home or apartment. Having plants like bonsais in the home can help to clean air and reduce respiratory infections in humans and pets. Other scientists suggest that having plants in the home can help to reduce stress, reduce blood pressure, and may, even, improve productivity.  

That’s why one of the best quirky things to do in Chicago is a bonsai workshop. The Color Cocktail Gallery is one of the best sites in Chicago for learning bonsai skills. Color Cocktail Gallery offers BYOB bonsai workshops! Also, their BYOB terrarium workshops are some of the most fun things to do around Chicago for couples. 

11. Try a Glass Blowing Class

If you enjoy working with your hands and learning new skills, you just might enjoy glass blowing. This experience can also make a great gift for a relative when they visit Chicago. You could also bring a significant other who is a thrill-seeker, or who has interests in mechanics or chemistry. 

glass blowing

One of the cool places to visit in Chicago is Shatter Glass Group on Chicago’s northwest side. During your class, you’ll learn so much about the glassmaking process and you’ll get to try things out in a safe environment. 

When you’re there in person, it can seem somewhat scary being surrounded by so many unbelievably hot surfaces. You’ll hear about how glass can explode if cooled too quickly…There is an edge of intensity and exhilaration involved in this class.

handmade glass blown bowl

It’s definitely not one of the places to go in Chicago for wimps, but that’s the fun of it! 😉Our instructor was careful to ensure our safety during participation. In the end, we walked away with 2 colorful glass bowls. It may not be one of the conventional Chicago tourist attractions, but you’ll walk away with a memento you can keep for life.

12. Shop at unique stores 

If you like thrifting or hunting down odd items, shopping can also be one of the unique things to do in Chicago.

If you’re looking for trendy clothing and accessories, or discounted designer items, you should check out Crossroads Trading. This may not be the most unique shopping Chicago has to offer, but it’s certainly an unusual place to find awesome stylish items. Crossroads can help you to plan exactly what to wear in Chicago. 

I’ve also had a ton of luck thrifting at the Salvation Army at 2270 N Clybourn Ave in Chicago. This Salvation Army is located Chicago’s wealthy Lincoln Park neighborhood, so it’s not uncommon to find brand names and clothing still with tags. They also have an excellent selection of books! 

woman wearing fashionable outfit in CHicago

The Brown Elephant stores are great for furniture thrifting. There’s a couple of stores in Chicago, and each has a unique variety of items. 

Aside from clothes and furniture, Woolly Mammoth Antiques and Oddities offers strange and unique knick-knacks and trinkets for the home. Finding quirky things here is one of the unforgettable things to do in Chicago. 

P.O.S.H. offers new and vintage tableware, kitchen tools, and dining accessories. It’s another one of the unique stores in Chicago.

woman stands in front of Wicker Park Mural in Chicago, 'I love Chi"

Myopic Books, in Wicker Park, is known as Chicago’s best used book store. Precious Possessions, near Millennium Park, offers jewelry featuring rocks, minerals, fossils, and carvings from around the world. Merz Apothecary sells international lines of bath and body care, as well as a variety of natural and organic health products. They have one store downtown and one on Chicago’s northside. 

You may also consider the American Science and Surplus store as well as the Wicker Park Secret Agent Supply Company. As you can see, Chicago offers unique shopping opportunities for scientists, fashionistas, moms, secret agent enthusiasts, and hipsters alike.

Shopping is undoubtedly one of the best things to do in and around Chicago. 

13. Check out Eataly Events

While most know of Eataly for its restaurants and market, many don’t realize that Eataly has far more to offer. Eataly offers an array of unique foodie experiences at their Chicago location. Eataly is certainly one of the must see places in Chicago!

Eataly events are some of the best Chicago winter activities (although, they are fun year-round). At Eataly, you can sign up for cooking classes, cocktail making classes, wine tastings, cheese tastings, chef competitions, and more! Some of the best activities to do in Chicago can all be fount at Eataly. 

Every once and a while Eataly even throws all-you-can-eat, all-you-can-drink, buffet-style parties. You can usually find one of these around the holidays. Eataly’s feasts are one of the best things to see in Chicago!

Eataly parties are always top-notch! Complete with fun decorations, activities, art, and delicious food. They’re not exactly the most weird things to do in Chicago, but they’re a blast! 

 These big events usually sell out quickly, so don’t wait to purchase your ticket. Events change month to month, and there is always something new and exciting offered. For more information about their current schedule, click here.

14. Enjoy Adler After Dark Nights

Visiting the Adler Planetarium is one of the most popular things to do in Chicago in November. The Adler Planetarium became America’s first planetarium in the 1930s. 

During regular museum hours, you can find a multitude of space-themed shows and exhibits at the Adler Planetarium. After hours, they offer exclusive access to individuals aged 21+ for special themed events. 

photo taken of couple at Adler Planetarium with cosmos in background

You need to purchase tickets in advance to participate in Adler After Dark Events. Their activities are some of the most fun things to do in Chicago for adults. Events vary throughout the year. They include special themes, activities, and lectures. 

No matter if you’re looking for exciting scientific discover or a fun challenge, Adler events are some of the most interesting things to do around Chicago. 

At these events, you’ll also find bars that serve out-of-this-world cocktails. Trying fancy dry ice cocktails is also one of the coolest things to do near Chicago.

15. Go to a Full Moon Jam

If you love EDM (electronic dance music), you’ll love Chicago’s Full Moon Jam community. Going to a Full Moon Jam is one of the cool things to do in Chicago.

The full moon jam is a regularly scheduled event where free spirits come together to celebrate the full moon. Seeing a full moon is one of the romantic things to do in Chicago.

woman performing fire dance with hoop

At full moon jams, you’ll find singing, dancing, LED lights, and amazing fire performances. Everything from fire hooping, fire poi, fire staff to fire fan dancing. The fire performers take turns on stage encircled by drummers and musicians. 

These events also draw in performers from other flow arts which often enhance their dance with glowing LEDs. The full moon jams are held in the park near Montrose beach. It’s one of the Chicago must-see attractions for locals. 

For more information, and to find the next scheduled full moon jam, visit their website here.

16. Experience Chicago Salsa Nights

Unbeknownst to most, Chicago hosts a vivacious Latin dance scene. Many hotels and bars have weekly or monthly “Salsa nights.” These are some of the most organic places to see in Chicago for incredible dancing. 

During these nights, there is typically an introductory lesson in the first hour which is followed by free dance. Most places will have some type of drink plus entry combination fee. It’s one of the exciting things to do in Chicago at night!

There are usually dancers of all skill levels, including complete beginners. However, you can expect to see a few really impressive couples take over the dance floor. Watching dance pros in real life is one of the fun activities in Chicago. 

couple dances intimately

They are an absolute delight to watch. If you find that you enjoy this, it might spur a new interest to take lessons. In Chicago, you can find plenty of studios that offer deals and discounts for group salsa dance classes. 

Check out Dylan’s Tavern and Grill, Alhambra, or Palm Court at the Drake Hotel. 

17, Go to a drive-in movie theater 

The Davis Drive-in is Chicago’s pop up drive-in movie theater. Enjoying movies from the comfort of your own car isn’t one of the most common romantic things to do in Chicago at night, but it’s certainly an option!

At the Davis Theater, you can bring your picnic blanket and camp out on top of your car. Or, stay inside if it’s a little chilly. This is one of the best things to do in Chicago for adults. 

drive in movie theater

Bring a partner, a friend, or a family member. Or, enjoy alone. Enjoying movies is also one of the top things to do in Chicago by yourself. 

No matter who you’re with, this experience will surely get you out of your routine and remind you of your youth. It’s one of the best activities in Chicago if you’re looking for something unconventional. 

18. Unique Dining in Chicago

Dick’s Last Resort is one of the most unique places in Chicago to enjoy a little comedy. Dick’s is an American restaurant chain that’s notorious for outrageous employees and unconventional entertainment. 

If you’ve never been to Dick’s, it’s something you should experience in Chicago! The decor of the restaurant is wacky, and guests are given bibs and paper hats. The hats are one of several tools that the serving staff uses to roast you during your meal. It’s one of the most unique restaurants in Chicago! 

woman raises a glass at Chicago's alinea restaurant

If you’re looking for unique Chicago dining experiences for an upscale evening, you’ve got to get a reservation at Alinea. Alinea is one of only 20 restaurants in the world to earn 3 Michelin stars. It’s not easy to get a reservation, but it is one of the best couples experiences Chicago has to over. 

If you’re looking for one of the most unique bars in Chicago, consider Untitled Supper Club. Untitled is known for burlesque-style shows and events. They also have regular concerts and jazz nights with live music. 

woman looks out on to food served at Alinea

Another one of the fun dining experiences Chicago offers is at Carnivale Chicago. Carnival is a festive dining experience that includes live music, dancing, and delicious Latin food. 

19. Unique Museums in Chicago

The International Museum of Surgical Sciences is one of the most weird museums in Chicago. It’s perfect for anyone who’s not squeamish and loves history. 

One of the other fun places to explore in Chicago is the Federal Reserve’s Money Museum right in downtown! You’ll find some historical currency on display and fun references to Broadway’s famous Alexander Hamilton

You may also consider visiting the National Museum of Mexican Art. This is also one of the different things to do in Chicago, and one of the lesser-known art institutions in the city. 

unique experiences in Chicago pin

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