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Chicago, Illinois, is a city full of surprises. This Midwestern metropolis accommodates diverse desires, from its famous architecture and stunning skyline to the vast array of cultural hotspots. But did you know that Chicago also offers plenty of opportunities to explore the more unusual side of life?
Chicago is a city with a long and storied history. It was founded in the early 1800s by settlers looking for new opportunities in the West. Over the years, Chicago has grown into a major metropolitan area, home to millions of people from all walks of life. It is the 3rd largest city in the United States, after all.
Many people go to the Windy City to enjoy a day on the shores of Lake Michigan, shop on the Magnificent Mile, take in the Chicago skyline, and take advantage of the numerous world-class dining options.
Beyond the Chicago River, Millennium Park, hanging out at Cloud Gate, wandering the Art Institute of Chicago, and eating deep-dish pizza, you may not have time to do everything. Even so, there are many unique things to do in Chicago; you could spend your whole trip just crossing them off this list.
Most people will miss out on these bizarre attractions that make this city unique. If you’ve ever been hunting for unique things to do in Chicago, we’ve got you covered.
- Best Tours in Chicago
- Unique & Unusual Things to Do in Chicago, Illinois
- 1. The International Museum of Surgical Sciences
- 2. Take a Yoga Class in a Brewery
- 3. Go on a Ghost Tour
- 4. Visit the Baha’i House of Worship
- 5. The Wicker Park Secret Agent Supply Co.
- 6. Visit the National Museum of Mexican Art
- 7. Go to a Second City Show
- 8. Find the Shit Fountain
- 9. Visit The Red Lion Pub
- 10. Visit the Illinois Holocaust Museum
- 11. Stroll Through Printer’s Row
- 12. Go to a Magic Show at a Speakeasy
- 13. Visit the Robert J. Quinn Chicago Fire Academy
- 14. Busy Beaver Button Museum
- 15. Follow the Yellow Brick Road to Oz Park
- 16. Explore the Underground Pedway
- 17. Visit The Wiener’s Circle
- 18. Turtle Race at Big Joe’s
- 19. Hang at Al Capone’s Favorite Spot, The Green Mill
- 20. Check out Dusty Groove
- 21. Take a Segway Tour of Chicago’s Lakefront
- 22. Medieval Torture Museum
- 23. Woolly Mammoth Chicago Antiques & Oddities
- 24. Graceland Cemetery
- 25. Visit the Crown Fountain
- 26. Enjoy Nature at the Garfield Park Conservatory
- 27. McCormick Bridgehouse & Chicago River Museum
- 28. Embrace Your Inner Homer Simpson on a Donut Walking Tour
- 29. The 606 (Bloomingdale Trail)
- 30. Leather Archives & Museum
- 31. Grab a bite at the Chicago French Market
- 32. Osaka Japanese Garden or Garden of the Pheonix
- 33. Northerly Island
- 34. No Pants Subway Ride
- 35. Noble-Seymour-Crippen House
- 36. Smart Museum of Art
- 37. Pilsen Murals
- 38. Devon Avenue
- What are some things that make Chicago unique?
- What are five things that Chicago is known for?
- What is the prettiest part of Chicago?
- What is the most famous thing in Chicago?
Best Tours in Chicago
Looking to get a unique perspective of Chicago's skyline? Then hop aboard one of our popular Chicago Architecture River Cruises! You'll cruise down the scenic Chicago River while learning all about the city's iconic buildings from your onboard guide. This is a great way to see some of Chicago's most famous landmarks, including Navy Pier, the Wrigley Building, and the John Hancock Building.
Looking for a unique and spooky way to explore Chicago? Then look no further than the Gangsters and Ghosts Tour! This tour takes you on a cruise down the Chicago River to see some of the city's most famous architecture. With commentary from your onboard guide, you'll learn all about the history of Chicago, including its gangster past and haunted sites. You'll also get to experience the dark past of one of Chicago's most frequented areas, the Loop.
If you love food, this is the tour for you! On the Chicago Food Tasting Tour, you'll sample some of the city's most iconic foods, including deep-dish pizza, hot dogs, Italian beef, and delicious pastries. You'll also get to explore some of Chicago's most beautiful spots, like Millennium Park, Michigan Ave, and the Riverwalk. This is the perfect tour for anyone who wants to experience the best of what Chicago has to offer!
Unique & Unusual Things to Do in Chicago, Illinois
1. The International Museum of Surgical Sciences
The International Museum of Surgical Sciences has to be at the top of the list of unique things to do in Chicago. This museum is the only one in the world devoted to surgery. It houses a collection of artifacts and exhibits documenting the history of surgery, from early surgical instruments to modern-day medical technology.
It’s like a game of Operation that’s gone wrong. The goal is to educate people in surgical science, of course, and they do so through a wide range of multimedia experiences.
If you’re a little squeamish, this isn’t the place to tour and have fun with hands-on exhibits right after you’ve had a deep-dish pizza. If you’ve ever wanted to see an extensive collection of heart valves, this Museum of surgical science is the place to go.
2. Take a Yoga Class in a Brewery
Address: 3340 N Kedzie Ave, Chicago, IL 60618
Take a yoga class in a brewery! In Chicago, several breweries offer yoga classes. One of the breweries that offer yoga is Revolution Brewing. Participants can enjoy beer during and after yoga, with the class accessible for all ability levels.
Classes vary in length, but most are around an hour long. After the class, you can enjoy a pint of beer or two. If you’re not a beer fan, don’t worry – most breweries also offer non-alcoholic beverages.
So, if you’re looking for a unique way to relax and unwind, be sure to check out a yoga class at one of Chicago’s breweries! After all, what could be more Midwestern than a beer-related activity?
3. Go on a Ghost Tour
Unsurprisingly, Chicago is known for being one of the most haunted cities in America. Between our ties to the Mafia, the numerous city tragedies like the Great Chicago Fire, and battles in the city bounds, the Windy City is bound to be rife with ghosts.
That’s probably why ghost tours are offered year-round in Chicago. Many of them will take you through some of our most haunted places, like Death Alley behind the now Nederlander Theatre, which stands on the former site of the Iroquois Theatre.
Death Alley is named as such because of how many of the 600 people fell to their death in the alley or their bodies were piled there as they were taken from the building.
Chicago’s numerous ghost tours offer an up-close and personal look at some of the most haunted places in the city, and you’ll get to hear firsthand accounts from people who have experienced paranormal activity. In case you’re after a spooky way to spend an evening in Chicago, be sure to check out one of the city’s best ghost tours.
If you’re itching to take your spooky stay a little further, there are a few haunted hotels in the city. The Congress Plaza Hotel downtown is largely considered the most haunted hotel in the city. Supposedly even Al Capone himself haunts this place.
4. Visit the Baha’i House of Worship
Address: 100 Linden Ave, Wilmette, IL 60091
Though not technically in Chicago, the Baha’i House of Worship is too incredible not to include. It is located in Wilmette, Illinois, and is one of only eight Baha’i Houses of Worship across the globe.
An Iranian architect designed this unique structure, a must-see for anyone interested in architecture or religion. Of the other Baha’i temples in the world, the one in Wilmette is indeed the oldest, as it opened in 1953.
The Baha’i House of Worship is open to people of all faiths and offers a variety of programs and events open to the public. Visitors can take a self-guided tour of the Baha’i House of Worship, attend a devotional service, or participate in one of the many educational programs.
See Related: Things to Do in Bloomington, Illinois
5. The Wicker Park Secret Agent Supply Co.
Formerly known as The Boring Store and Not a Secret Agent Supply Shop, this normal gift shop is normal. There is nothing to see here that is out of the ordinary. Don’t worry; the pigeons inside are not watching you.
That said, if you’re ever feeling bored while visiting the Windy City, you could see The Wicker Park Secret Agent Supply Co. You can come here to buy normal objects for your family or loved ones. If you see secret agent trinkets for sale, you didn’t.
Just remember, there are laws against things like wiretapping unless you’re an NSA agent; then, by all means, listen away. Talk to your handler over the mini walkies you got at this store. Most importantly, ensure no one knows you’ve decided to go. After all, there’s nothing to see. Move along.
6. Visit the National Museum of Mexican Art
Address: 1852 W 19th St, Chicago, IL 60608
Housed in Harrison Park in the largely Latinx neighborhood of Pilsen, you can find The National Museum of Mexican Art. Originally known as the Mexican Fine Arts Center Museum when it opened in 1987, the current museum building was opened in 2001, and its name changed in 2006.
This museum houses a collection of art and artifacts from Mexico and other Latin American countries spanning over 3600 years. This is a great place to learn about the history and culture of Mexico and the Americas.
In total, there are more than 18,000 artworks housed in the museum. Some of their collection highlights include Miguel Cabrera’s Virgen de Guadalupe (circa 1740), Carlos Cortéz’s Homage to Posada (circa 1981), and Favianna Rodríguez’s Invisible Sun (circa 2008).
7. Go to a Second City Show
Chicago is known for its improv comedy scene. Namely, it’s known as the birthplace of Second City. Named for one of Chicago’s nicknames, Second City has cropped up elsewhere in the world, including Toronto and L.A. Still, Chicago’s iteration has launched the careers of many comedians through the years.
Some comedy greats like Chris Farley, Tina Fey, Bill Murray, Steve Carell, and Shelley Long started here. They’re in good company with lots of other comedians who used Chicago’s Second City as a springboard. Who knows, maybe you’ll see the next Alan Arkin!
Theaters like Second City and iO offer shows most nights of the week, and tickets are usually very affordable. Next time you’re looking for something to do in Chicago, be sure to check out one of the city’s many improv shows.
8. Find the Shit Fountain
Address: 1001 N Wolcott Ave. Chicago, IL 60622
It’s literally what it says it is. It is a large statue of dog poop. Jerzy K. Kenar was fed up with dogs stumbling into flowers and going to the bathroom on them. So, he decided to take matters into his own hands and craft a statue from metal that’s shaped to look like, well, poop. He then positioned it on a fancy sandstone table shaped to fit a Grecian bust.
And though it may be crude, it’s now well respected by community members. There’s even a crazy rumor floating about that if you actually drink water from it, you can cure a really bad case of constipation.
If you find yourself in the area and feel brave enough, maybe try it. You might be the next one spreading the word about the magical Shit Fountain and its ability to cure all that ails you.
See Related: Things to Do in Detroit
9. Visit The Red Lion Pub
Address: 2446 N Lincoln Ave, Chicago, IL 60614
For some people, a traditional English pub in Chicago qualifies as a unique Chicago attraction. However, add numerous ghost sightings, and you suddenly add another level of bizarreness to your experience hence why the Lincoln Park dwelling Red Lion made a list.
The building that is home to The Red Lion Pub was built in the late 1800s, but John Cordwell wanted to renovate the place a little. Among other things, he added a stained glass window that causes people to get dizzy and sense the presence of someone… or something nearby. Cordwell thinks it could be his father. Some say they smell lavender, while others say apparitions can be seen in the women’s restroom.
This is one of the places I go to when I’m dearly missing London. Sometimes you need a good pub cheese or a proper fish and chips, you know? Ghosts or not, this is one of my favorite spots in the city.
10. Visit the Illinois Holocaust Museum
Address: 9603 Woods Dr, Skokie, IL 60077
Another location that is not in Chicago is still well deserving of a place on this list. Unique to describe this museum sounds diminutive, but it isn’t meant to be. It is simply a way of saying this location is one-of-a-kind and may not be top of mind when visitors think of Chicagoland.
Opened in 2009 after 30 years of hard work by a group of Holocaust survivors, The Illinois Holocaust Museum and Education Center push back against bigotry and hatred. This museum is dedicated to documenting the history of the Holocaust.
Here you can find permanent exhibits on topics such as Interactive Holograms: Survivor Stories Experience, The Warsaw Ghetto Uprising, and Rescue and Renewal: The Jewish Cultural Reconstruction Collection of The Hebrew Theological College. Plus, the museum has visiting exhibits on tangential topics like post-war rebuilding or the American Civil Rights movement.
See Related: Things to Do in Rockford, Illinois
11. Stroll Through Printer’s Row
Address: 5050 N Clark St, Chicago, IL 60640
During the late 1800s and early 1900s, Chicago was home to the booming print industry. Printer’s Row, located on Dearborn Street just south of downtown, was filled with printing presses, paper suppliers, and bookbinders.
These days, Printer’s Row has mainly been replaced by high-rise apartments and office buildings. However, visitors can still get a sense of the area’s history by browsing the bookstores and cafes that line Dearborn Street or glimpsing the variety of architecture up and down the street.
Some of the neighborhood’s former major publishing companies include R.R. Donnelley & Sons, Rand McNally, and Franklin Printing. So be sure to also take time to admire the murals on the Franklin Building, which depict scenes from Chicago’s printing past.
Should you want to keep your head in the books during your visit, consider staying at The Publishing House Bed and Breakfast. This hotel is in a former publishing house, hence the name, and is a charming B&B with easy access to the rest of the city.
12. Go to a Magic Show at a Speakeasy
Address: 5050 N Clark St, Chicago, IL 60640
Usually, speakeasies use bookshelves to hide their secret door. That’s not the case at Chicago Magic Lounge. The lounge is located in a speakeasy built in a 1940s laundry house, so it’s only fitting that laundry machines hide the door at this Chicago establishment.
The Chicago Magic Lounge is committed to keeping the art of magic alive with several shows featuring jaw-dropping tricks that will leave you questioning how they were even possible. But after a few drinks, you won’t care if you can’t figure out their tricks.
These shows take place in a small, intimate space which only adds to the appeal and makes you feel like you’re in on a secret. When it comes to unique things to do in Chicago, you don’t get much more unique than the Chicago Magic Lounge.
When you can’t escape the thrill of a speakeasy, you’ll be glad you booked a room at the Old Chicago Inn. This boutique hotel features an actual speakeasy that guests can visit but also has local members who hang out there.
13. Visit the Robert J. Quinn Chicago Fire Academy
Address: 558 W De Koven St, Chicago, IL 60607
If you’re ever in Chicago, you’ll want to check out the Robert J. Quinn Chicago Fire Academy. This unique facility offers tours, classes, and exhibits that educate and enlighten visitors of all ages.
The Academy is an essential visit for anyone interested in firefighting or Chicago public safety since this is where the city’s firefighters are trained. You can find it near the Little Italy / University Village neighborhood on the city’s Near West Side.
Fittingly, the academy was built on the former site of Mr. and Mrs. O’Leary’s farm. It is rumored that the Great Chicago Fire of 1879 originated on that farm. To memorialize the land the academy is on, a statue titled Pillar of Fire can be seen in the front of the building.
14. Busy Beaver Button Museum
Address: 3407 W Armitage Ave, Chicago, IL 60647
If you desire unordinary things to do in Chicago, check out the Busy Beaver Button Museum. The Busy Beaver Museum is the world’s only pin-back button museum!
This unique museum is dedicated exclusively to the history and culture of pin-back buttons and features collections dating back to 1896, the year the pin-back button was patented. Beyond that, they also have pre-pin-back buttons from George Washington’s inauguration and Abraham Lincoln’s presidential campaign.
This free museum has over 30,000 pins on display, highlighting their evolution and the many themes pins can have. And of course, no visit to the Busy Beaver Button Museum would be complete without picking up a few souvenir buttons to take home with you!
15. Follow the Yellow Brick Road to Oz Park
Address: 2021 N Burling St, Chicago, IL 60614
Oz Park is one of those places in Chicago that makes sense once you’re here. The park, located in the historic Lincoln Park neighborhood, was purchased by the city in 1974 and has since grown into a wonderland.
This park was inspired by the iconic 1939 musical adaptation of L. Frank Baum’s fantasy novel the wonderful Wizard of Oz. Why? Because Baum was living in Chicago when he wrote It! So, if you follow along the yellow brick road in Lincoln Park, you’ll find statues of Scarecrow, Tin Man, Toto, Cowardly Lion, and Dorothy on-site, making for some great photo ops.
Oz Park is also a great place to catch a concert or two – there’s always some live music or something happening here in the summer. So if you’re ever in Chicago, be sure to check out Oz Park.
16. Explore the Underground Pedway
Chicago’s Pedway is a system of underground tunnels and walkways downtown that connects buildings in the central business district. There are nearly 50 entry points for the Pedway, including entrances at Millennium Park, the Grant Park underground garages, and near Macy’s on State Street.
One of the reasons locals love the Pedway is because it’s a traffic-free way of getting around downtown. More importantly, it’s one way to stay warm in the bitter Windy City winters or avoid the rain.
The Pedway includes connections to the Chicago subway system, making it a vital link for tourists and residents. While it may seem strange to see people walking underground, it is a fun way to experience downtown Chicago. It almost feels like being on a secret mission.
17. Visit The Wiener’s Circle
Address: 2622 N Clark St, Chicago, IL 60614
When it comes to random things to do in Chicago, you can’t get more random than stopping by The Wiener’s Circle. So they serve Chicago-style hot dogs, okay? What makes them special? Well, you’ll have to show up and find out.
The Wiener’s Circle is a restaurant where you should expect verbal abuse. Like another surly spot Ed Debevic’s, this Lincoln Park institution serves diner food with a side of sass.
If you can’t handle this weird Chicago snark factory, you might want to stay away from The Wiener’s Circle. No judgment; not everyone can be a wiener.
18. Turtle Race at Big Joe’s
Address: 1818 W Foster Ave, Chicago, IL 60640
Did you think a list of offbeat things to do in Chicago would include racing turtles? Well, it does. You, too, can enjoy turtle racing if you stop by on a Friday night at Big Joe’s. Big Joe’s is a bar in Lincoln Park that hosts turtle races with their five resident turtles.
The racing turtles are Chucks, Doozy, Swisher, Lucky Dan, and Jolanda. Turtle racing is a great way to support the community and have a chance to win prizes. To enter the turtle race, you must show up at Big Joe’s in person and buy drinks at the bar, where you’ll receive raffle tickets.
If your raffle ticket is called, you can enter the next turtle race of the night. If your turtle wins their race, you get a t-shirt, and if your turtle comes in last, you get a free drink! At the end of the year, all the winners are entered into a big raffle for a trip!
19. Hang at Al Capone’s Favorite Spot, The Green Mill
Address: 4802 N Broadway, Chicago, IL 60640
Once owned by mobster “Machine Gun” Jack McGurn, an associate of Al Capone, this prohibition-era speakeasy is still a jazz hot spot. Capone himself had a special booth he always occupied. From there, Capone could see both the front and back doors to keep an eye out.
The Green Mill has operated as a social gathering place for over a hundred years. It may also be the country’s oldest, continuously running jazz club. Its shimmering marquee is begging visitors to experience this piece of Chicago history.
Jazz pours out of this lounge every night. It’s a charming place that shows guests another side of Chicago. Also, it closes at 1:11 a.m. every night, and no one will show you the mob’s trap door or tunnel system. Why? Mind your business, that’s why.
20. Check out Dusty Groove
Address: 1120 N Ashland Ave, Chicago, IL 60622
Dusty Groove is a large airy store stocked with new, used, and rare LPs and CDs. DJs Rick Wojcik and JP Schauer opened the first iteration of Dusty Groove in 1996 as an online-only record shop. Now they have a brick-and-mortar spot, too, as well as their enormous inventory online.
The DJs started selling their vinyl through direct mail not long before their business expanded internationally and was recognized. It now has the rarest vintage records and music unusualities at very low prices. Despite its fame, Dusty Groove’s homey characteristics make it top of the list of unique things to do in Chicago for music lovers.
As a traveler, you’ll appreciate Dusty Groove’s massive collection of records as well as its commitment to affordability.
21. Take a Segway Tour of Chicago’s Lakefront
Segway tours are the perfect way to see all the sights of Chicago’s lakefront while simultaneously getting a (slight) workout. Several companies offer Segway tours along Lake Michigan, so be sure to check them out.
Segways are easy to use and maneuver, making them the perfect mode of transportation for exploring new places. Plus, you get impressive views of the Chicago skyline from the paths.
These Segway tours are also great for meeting new people and making friends. So what are you waiting for? Go on a Segway tour of Chicago’s lakefront today.
22. Medieval Torture Museum
Address: 177 N State St, Chicago, IL 60601
At the top of the list of weird things to do in Chicago is undoubtedly the Medieval Torture Museum. This strange museum is an eight-room attraction showcasing the most gruesome torture practices ever performed.
The museum displays a colorful display of silicone dummies and various torture instruments. Each exhibit resembles a diorama of violence, with the dummies in horrific pain as their bodies are placed on the device. You probably don’t want to bring children to this place, especially youngsters under 12 or 13. It’s pretty graphic.
Each exhibit teaches you how the practice was used, but there is also an audio guide with a surprisingly haunting voice. The Medieval Torture Museum is a great place to learn about the dark side of history, and it’s also a great place to get some scares. If you’re squeamish, you might want to stick to something like the Chicago History Museum or the Art Institute instead.
23. Woolly Mammoth Chicago Antiques & Oddities
Address: 1513 W Foster Ave, Chicago, IL 60640
Woolly Mammoth Antiques & Oddities is a must-visit shop for anyone in Chicago looking for weird places. Founded in 2010, the store has an impressive collection of bizarre, curious, and interesting items.
They’ve got medical oddities, preserved bones, obsolete medical tools, and even taxidermy. In addition to the wide variety of items on display, Woolly Mammoth also offers a range of courses on topics such as taxidermy and bone collecting.
Don’t forget to bring your sense of humor if you wander to Andersonville to explore this fascinating shop. Irrespective of your search for a unique souvenir or want to browse through some of the most unusual items, Woolly Mammoth Antiques & Oddities is your spot.
See Related: Top Helicopter Rides in Chicago
24. Graceland Cemetery
Address: 4001 N Clark St, Chicago, IL 60613
Graceland Cemetery in Chicago is not your typical vacation spot. But it should be on your list of places to visit while in the Windy City. Graceland opened in 1860 and is one of the nation’s oldest landscaped cemeteries listed on the National Register of Historic Places. Consider this the most haunted place on this list.
The cemetery, which covers 119 acres, is known for its lovely monuments, mausoleums, statuary, and quaint chapel. Regarding unique things to do in Chicago, we’re dead serious that this is the most macabre.
Graceland is also the final resting place of many notable figures from Chicago’s past, including architect Daniel Burnham, Joseph Medill of the Chicago Tribune, Jack Johnson, the first African-American world heavyweight boxing champ, and Ludwig Mies van der Rohe, the renowned architect.
A visit to Graceland Cemetery is a unique way to learn about Chicago’s history and architecture – and to pay tribute to those who have made this place so great. While it’s known for its hauntings, it is also a beautifully maintained final resting place.
25. Visit the Crown Fountain
Address: 201 E Randolph St, Chicago, IL 60601
If you find yourself in Chicago, one of the best things to do is visit Millennium Park near Lake Michigan. This internationally acclaimed park has remarkable attractions like Cloud Gate and the Crown Fountain.
This massive fountain is one of the largest in the world and features two towers of glass brick that spout water. Surrounded by lights, the towers also display video footage of one of a hundred citizens in the city.
Each tower is 50 feet tall, and the LED rotates the images every minute. While the Crown Fountain is certainly an impressive sight, it’s also meant to be interactive. Visitors can splash around the shallow reflection pool or walk through the towers.
So, whether you’re looking to cool off on a hot day or take in some of Chicago’s finest architecture, add the Crown Fountain to your list of essential destinations. You can say you got “spat on” at Millennium Park. Don’t worry; the fountain people are pretending to spit on you.
26. Enjoy Nature at the Garfield Park Conservatory
Address: 300 N Central Park Ave, Chicago, IL 60624
Opened in 1908, the Garfield Park Conservatory is one of the largest conservatories in the country. Home to thousands of plants, the conservatory is a great stop for the whole family — especially if you visit the Windy City in the wintertime.
Garfield Park Conservatory has nine distinct areas to explore, including the outdoor gardens, the Aroid House, and the Palm Room. My personal favorite part of the conservatory is the Palm Room, with its massive domed ceiling.
The Show House showcases different exhibits depending on the time of year. It’s really fun to visit during the holiday season when you can see the lively poinsettias (their original Aztec name for the plant is cuetlaxochitl) bringing color back to the city.
27. McCormick Bridgehouse & Chicago River Museum
Address: 99 Chicago Riverwalk, Chicago, IL 60601
The McCormick Bridgehouse & Chicago River Museum is a great place to learn about the history of Michigan Avenue Bridge and see it from above! The museum is located at the intersection of the avenue and the bridge, which makes it a unique location.
Many people don’t even know that this museum exists because it’s tucked away at this intersection along the Chicago River. Nonetheless, the museum is undoubtedly worth checking out, especially if you’re interested in learning about the bridge systems of the Chicago River and its relationship with Lake Michigan.
This is a different kind of Chicago history museum. If you ever visit Chicago downtown, stop by McCormick Bridgehouse Museum for an informative and interesting experience.
28. Embrace Your Inner Homer Simpson on a Donut Walking Tour
Looking for a unique way to explore Chicago? Why not try a donut-themed walking tour? This original donut walking tour takes you to some of the best donut shops in town, all within the Chicago Loop.
Tastings are included so that you can sample signature flavors from each shop. And don’t worry if you have dietary restrictions – plenty of vegan, gluten-free, and nut-free options are available.
This is a great way to see some of the most iconic sights in Chicago while indulging in a sweet treat at the same time. When you stop at Stan’s Donuts during the tour, I highly recommend getting a Chocolate Lightning to keep you going. It’s their in-house cold brew mixed with chocolate milk; you’re welcome.
29. The 606 (Bloomingdale Trail)
The 606 is a trail that was initially known as Bloomingdale Trail. The trail has a longstanding goal of creating more vibrant outdoor spaces in Chicago. The 606 was created after numerous collaborations and meetings by various groups, community associations, and non-profit organizations.
The Bloomingdale Trail is a unique place of interest in Chicago. Its public recreation space features walking, running, and biking paths, combining heritage and architecture to create an idyllic, relaxing place. It spans so much of the city you can see a wide range of its greenery.
The 606 is also home to many events open to the public throughout the year and are sure to be enjoyable for all ages. It’s an incredible way to walk around the city without the hustle and bustle of downtown.
See Related: Best Hiking Trails in the United States
30. Leather Archives & Museum
Address: 6418 N Greenview Ave, Chicago, IL 60626
Chicago’s Leather Archives & Museum is undoubtedly a unique stop for travelers, but it merits a stopover! This museum is dedicated to celebrating BDSM and leather culture and features an array of equipment displays, artifacts, and literature libraries. It is undoubtedly the kinkiest museum on this side of Lake Michigan.
You can discover everything from chain-swapping whips to handcuffs, bondage equipment, and leather clothing at this museum. In addition to being a fascinating glimpse into an often misunderstood subculture, the Leather Archives & Museum is also rich in history, with details about the cultural aspects of fetishism, its roles in the LGBT community, and an academic discussion about the taboos surrounding BDSM.
When searching for an anomalous activity to add to your Chicago itinerary, the Leather Archives & Museum is where it’s at. Keep in mind that this museum is 18+.
31. Grab a bite at the Chicago French Market
Address: 131 N Clinton St, Chicago, IL 60661
Chicago’s French Market is wonderful for enjoying French food and other European-inspired cuisines. With over 30 suppliers, ranging from restaurants serving French food to dining, the market is the perfect place to enjoy international flavors all in one place. The market is also a great place to shop for groceries and products.
The French Market is Chicago’s original food hall downtown. While you never have to go far in the city for a good meal, the most appealing aspect about spending time at the French Market is that you’ll be steps away from multiple other local favorite attractions.
In addition to the market, Chicago’s French culture is also evident in its museums and art galleries that showcase the work of French artists, as the Art Institute of Chicago has the most extensive collection of Impressionist work outside of France.
32. Osaka Japanese Garden or Garden of the Pheonix
Address: 6300 S Cornell Ave, Chicago, IL 60637
This gorgeous outdoor space was created in 1893 in Jackson Park by Japanese landscape architect Tatsuo Ishimoto. It is still widely referred to as the Osaka Japanese Garden but is now known as the Garden of the Pheonix.
The garden was created for the World’s Columbian Exposition in Chicago and is one of the remaining artifacts from the fair. The other Hyde Park remnant is the Museum of Science and Industry. The Garden of the Pheonix features multiple ponds, bridges, and statues and contains a replica of a Torii gate, a traditional Shinto symbol.
When you visit the garden, you can wander the winding paths, relax by the pond, and enjoy the tranquil atmosphere. The garden is open daily from dawn to dusk, and admission is free.
33. Northerly Island
Northerly Island is a 120-acre peninsula city park along Lake Michigan, south of Adler Planetarium but east of Soldier Field. It isn’t quite an island but is devoted entirely to nature, with breathtaking walking pathways and remarkable views across the downtown Chicago skyline among its highlights.
The manmade peninsula was the site of the Century of Progress World Fair in 1933 and was planned by architect Daniel H. Burnham. It was supposed to be one of a series of islands spanning Grant and Jackson Parks but was the only one ever built.
Today, Northerly Island is an excellent spot for a picnic or a walk, perfect for bird-watching. The preserve is a stopping point for migratory birds and is home to over 150 species of native plants. Not to mention the over 20,000 trees and shrubs on the peninsula. It feels like a world away from the hectic life in the city.
34. No Pants Subway Ride
Not that Chicago’s trains aren’t weird enough, but the annual No Pants Subway Ride makes them even weirder. This annual event encourages riders to take off their pants when the train arrives, then act as if nothing happened.
The purpose is to confuse and amuse their fellow passengers. Although the No Pants Subway Ride is a national event, it’s still unique to Chicago, where it occurs on the Red Line from Loyola Station to downtown.
When searching for a unique experience during your next visit to Chicago, hop on board the No Pants Subway Ride. Just be aware it usually happens in January. (It’s pretty cold in Chicago in January).
See Related: Useful Tips for Long-Distance Train Travel
35. Noble-Seymour-Crippen House
Address: 5624 N Newark Ave, Chicago, IL 60631
If you’re looking for a taste of Chicago history, the Noble-Seymour-Crippen House is a must-see. This historic building dates back to 1833 and is listed on the National Register of Historic Places. It is rumored to be the oldest building in the city, though folks debate that at length.
During the home tour, you’ll see excerpts from the notebooks of an older daughter, one of the home’s former inhabitants. The museum facilities also provide a fascinating glimpse into life in early Chicago.
The southern wing of the home is the oldest, original portion, though the whole thing is like walking into a time capsule.
36. Smart Museum of Art
Address: 5550 S Greenwood Ave, Chicago, IL 60637
Smart Museum of Art is a must-see, free museum for connoisseurs of the arts visiting Chicago in Hyde Park. While Chicago is home to world-renowned museums like the Art Institute of Chicago, the Smart Museum of Art offers a more intimate experience.
Housed in a beautiful Beaux-Arts building on the University of Chicago campus, the Smart Museum is home to collections by renowned artists such as Degas, Matisse, and Rodin. Visitors can also enjoy rotating exhibitions as well.
Some previous temporary contemporary art exhibits at the Smart Museum have included Monochrome Multitudes, Smart to the Core, and Claudia Wieser: Generations. If contemporary art isn’t your speed, the rotating exhibits also demonstrate a variety of other modes and mediums.
37. Pilsen Murals
Pilsen is an energetic and diverse community with a rich history of art and politics. The Pilsen Murals are a testament to this history, and they continue to evolve and attract audiences today. These murals were first painted in 1976, depicting various aspects of political action and social interaction.
Originally inhabited largely by Bohemian immigrants, Pilsen has transformed into a Latin American community. Some of the best Mexican celebrations, events, and food can be found in Pilsen. Not to mention the incredible collection of street art murals.
The murals continue to be transformed by new artists, and it is now one of Pilsen’s most popular tourist attractions. Visitors can learn about the murals’ history and the community’s Latin American culture, all while enjoying the lively colors and powerful images.
See Related: Best Boutique Hotels in Chicago
38. Devon Avenue
Devon Avenue is one of the most important streets in Chicago’s Desi community. This part of Chicago is often referred to as Little India, and it is home to a large population of Indian Americans.
The avenue is lined with Indian restaurants, grocery stores, and other businesses catering to the local community’s needs. You’ll find all of your favorite dishes, from curry to korma. And if you’re looking to pick up a souvenir or two, Devon Avenue has plenty of shops to peruse.
What are some things that make Chicago unique?
Lake Michigan, for sure. Nonetheless, the history of Hyde Park, the importance of Michigan Avenue Bridge, and Willis Tower make our city unique.
What are five things that Chicago is known for?
Deep dish pizza, mobsters (especially the Valentine’s Day Massacre), Chicago dogs, Willis Tower, and Cloud Gate. The city’s history involving tragedies, the Great Chicago Fire, and music are also big parts of the city’s reputation.
What is the prettiest part of Chicago?
The lakefront, for sure, especially from an area like Northerly Island. Not only can you see the lake up close, but you can’t beat the city’s skyline views from here, either. Navy Pier also offers unparalleled views of the city from a distance.
What is the most famous thing in Chicago?
Cloud Gate in Millennium Park is probably the most famous thing in the city. It’s also known as The Bean. Yet, one could also argue that Chicago’s skyline is its most famous feature.
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Amanda is a Chicago-based queer travel, arts, and lifestyle writer who is passionate about exploring the world. Her work has been featured in Newcity Stage, The Chicago Reader, Huffington Post, and Yahoo, as well as the November 2022 book, “Chicago Like a Local” and other travel journals available on Amazon. Amanda’s favorite destinations include Costa Rica, Prague, Dublin, Hong Kong, and every Disney park she’s visited.