Grab your appetite and your boots folks – we’re taking a trip to the Windy City!
While it’s often overshadowed by the coastal juggernauts of L.A. and New York, Chi-Town trots to a rhythm all its own.
From eclectic neighborhoods packed with character to that iconic deep dish, hot jazz, and impressive skyline towering above Lake Michigan, Chicago’s definitely packed with plenty to keep you occupied!
Now, this cultural hub may have more than its fair share of interesting attractions, but if your plan is to venture off the beaten track, rest assured that America’s third-largest city’s got you covered. Indeed, there are heaps of hidden gems in Chicago that are just waiting to be discovered, so let’s take a look at them!
Photo: Sasha Savinov
What’s Chicago Like?
Whether you plan to take a food tour, cruise down the Chicago River, or ride the iconic Centennial Wheel, you bet there’s something in Chicago with your name on it!
While there are heaps (and I do mean heaps!) of secret spots in Chicago, the city also has plenty of world-famous landmarks that you can check out during your stay.
In addition to its gleaming skyscrapers, Chicago has numerous world-renowned attractions, including Millenium Park. Over there, you’ll find heaps of unique features, including the quirky Crown Fountain and Cloud Gate. If you’re traveling with kids, be sure to check out the Chicago Children’s Museum located on the Navy Pier.
Image: Nic Hilditch-Short
Of course, it wouldn’t be a hot Chicago trip without checking out the thrilling 360 Chicago Tilt Viewing Platform! Perfect for thrill-seekers, this platform is located on the 94th floor of the John Hancock Building. Given its status as one of Chicago’s best attractions, securing skip-the-line tickets is highly recommended to avoid long waits!
But wait – I’m here to look at the lesser-known stuff, not those ultra-popular attractions…so let’s check them out!
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When I first landed in the city, I never planned on straying off that well-trodden tourist trail. In fact, my Chicago itinerary was full of famous areas that I had planned on visiting.
However, it didn’t take me long to get tired of those loud swarms of tourists. And so, I decided to ditch my meticulously planned itinerary and venture off the beaten track in search of those lesser-known spots that offer a more authentic experience!
1. Relax at a Secret Pool
Here’s a real doozy as far as hidden gems in Chicago are concerned! Ironically enough, this secret pool is found in the Lincoln Park Conservatory, one of the most visited gardens in the city.
While the park is especially known for hosting flower shows in its Show, Orchid, Fern, and Palm Houses, not a lot of tourists know that there’s a hidden pool tucked away at the north end of the conservatory.
Designed by famed architect Alfred Caldwell, this hideaway was first developed back in the mid-1900s. It has since been listed on the National Register of Historic Places and became a National Historic Landmark in 2006.
Fringed by a Fullerton Gate, the pool is surrounded by a Midwestern-style prairie landscape, complete with a pavilion, stone outcroppings, and a waterfall arranged around the artificially heated creek. Bear in mind that this is considered a place of quiet reflection, so do try to keep your voice down.
The pool is currently closed for the season, but it’ll open again in May of 2024. It’s my favorite part of Chicago. It’s also home to my favorite hotel in the city – Villa D’ Citta.
- Rating: 10/10 – Bucket list essential!
- Cost: Free
- Personal Opinion: Definitely don’t skip this one!
2. See Inside Art Deco Masterpieces
It won’t take you long to notice that Chicago is full of gorgeous buildings and features. Many of them actually date all the way back to the Gilded Age.
The thing is, most visitors simply stroll past those spectacular masterpieces without actually going inside – which is why I recommend this walking tour that’ll take you smack inside these Art Deco masterpieces!
Not only will you discover some of the glitziest, most magical places in Chicago, but your guide will also tell you more about the city’s glamorous past.
Think speakeasies, jazz, gangsters, flappers…the whole shebang! Through this activity, you’ll even learn more about the infamous Crash of 1929 and how it shaped the future of the city.
Just a quick heads-up though: there’s a lot of walking involved (around 1.5 miles in two hours), so be sure to wear your comfiest travel shoes.
- Rating: 8/10 – Genuine Delight
- Cost: $35
- Personal Opinion: A true hidden gem, sure to make you smile.
3. Amble Through an Open-Air Art Gallery
Did you know there’s an actual open-air art gallery tucked away in the historic South Loop neighborhood? Well, I didn’t either until I accidentally stumbled upon the Wabash Arts Corridor while randomly ambling the city!
Perfect for art aficionados, this secret spot in Chicago is described as the city’s ‘living urban canvas’ – and it won’t take you long to understand why. It’s particularly fun to visit with people you meet at hostels in Chicago.
Photo: Raed Mansour (Flickr)
Artwork after artwork beckons as you walk through the corridor, each one more evocative than the other. Each mural has its own story to tell and if you’re lucky, you might even see a couple of artists in full action.
What makes this place doubly special is that the art scene is constantly changing, so there’s always something new to see. It’s certainly one of the best things to do when spending a weekend in Chicago.
- Rating: 7/10 – Hidden Gem Alert
- Cost: Free
- Personal Opinion: Well worth the detour for a unique experience.
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View on Osprey View on REI4. Enjoy a Yoga Session by the River
While the Chicago River is known for its great boating opportunities, did you know that you can even sign up for a yoga class right by the banks of the river?
Combining sightseeing, wellness, and relaxation, this activity also includes a stroll around the river. You’ll stop by idyllic locations to go through different types of stretches, meditative exercises, and flows.
Photo: Roaming Ralph
Best of all, this activity takes place early in the morning so you can enjoy this beautiful landmark before the crowds settle in. In addition to yoga, this activity also takes you past some architectural marvels like the Wrigley Building and Tribune Tower.
There are so many amazing yoga retreats in the US that’ll rejuvenate your body, and reset your mind.
- Rating: 7/10 – Hidden Gem Alert
- Cost: $44
- Personal Opinion: Well worth the detour for a unique experience.
5. Check Out the Secret Skyline at the Navy Pier
I know, I know. The Navy Pier’s ain’t exactly some huge secret. It’s right up there with all those top attractions in Chicago!
While it’s definitely not an underrated place, the Navy Pier is actually home to a hidden skyline view that’s found right above its parking garage. Cut through the usual gaggles of tourists swarming around the Navy Pier and make your way to the top floor which is usually devoid of crowds.
Photo: Sasha Savinov
From there, you will be able to see those historic and modern buildings alike in all their glory. For the best views, I would recommend that you head there shortly before sunset so you can see Lake Michigan shimmer under those golden rays in the distance. Afterward, you can unwind at one of Chicago’s best places to stay for the night.
- Rating: 10/10 – Bucket List Essential
- Cost: Free
- Personal Opinion: Don’t miss it! A must-visit gem of excellence.
| Best Hotel | Best Hostel | Best Private Stay |
|---|---|---|
| Curio Collection By Hilton | HI Chicago Hostel | Sky Home |
6. Uncover Secrets of the Prohibition Era
Ah, the Prohibition Era. That infamous time in Chicago when bootlegging and Al Capone-style gangsters were as common as those secret bars specializing in illegal boozing.
If you want to step back in time and explore those formerly illicit Chicago hideaways, you can always check out this private, 3-hour activity.
During this VIP tour, a local historian will lead you through those secret entrances that’ll lead you right to hotspots frequented by Chicago gangsters and bank robbers. You can even treat yourself to cocktails that were quite famous during the Prohibition Era.
I do need to point out that this activity is on the more expensive side. If you don’t mind splurging though, I think the experience is certainly worth it!
- Rating: 9/10 – Worth Bragging About
- Cost: $950
- Personal Opinion: An impressive find you’ll tell friends about.
7. Hop Aboard a Barrel Bus
Speaking of the Prohibition Era, here’s one of my absolute favorite ways of exploring those hidden gems in Chicago!
Ideal for groups of friends looking for unique things to do in Chicago, this brewery tour takes place onboard a Prohibition-Era-style Barrel Bus that’s as fun as it looks.
This one-of-a-kind brewery hopping offers a deep dive into some of the best locally-produced craft beers. You’ll see what goes on behind the scenes and even enjoy a glimpse of what breweries used to be like before Prohibition.
Of course, it wouldn’t be a brewery tour without those sampling sessions. Rest assured that you’ll be treated to a tasting session at each spot. Be sure to wear closed-toe shoes since you can’t wear open shoes at one of the brewery’s production rooms.
- Rating: 8/10 – Genuine Delight
- Cost: $100
- Personal Opinion: A true hidden gem, sure to make you smile.
8. Look for the Secret Mermaid Sculpture
There are TONS of places to visit in Chicago. You could spend weeks in this city and still find new things to see and do. If you’re looking for a hidden gem, be sure to check out the Secret Mermaid Sculpture at Oakwood Beach!
This lesser-known art piece depicts the statue of a mermaid that’s carved directly into the rocky outcropping. Her head is turned almost longingly towards the horizon.
What adds to the allure of the statue though is that its origins are somehow murky: some locals will tell you that it was erected long ago to pay homage to Lake Michigan’s many myths and legends.
Others will tell you that it’s a stray piece of art from the Gilded Age. Some even speak of a heartbroken sculptor who found solace while carving away by the ocean’s edge.
Over the recent years though, it emerged that the statue was carved by four sculptors in 1986. At first, the mermaid was kept hidden because the artists never got permission to carve into the outcropping. However, it was rediscovered by the U.S. Army Corps of Engineers in 2000 and has since become a local secret.
- Rating: 6/10 – Worth a Deeper Look
- Cost: Free
- Personal Opinion: There’s substance under the surface.
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View on REI Read Our Review9. Uncover the Secrets of the Institute for the Study of Ancient Cultures
I’m sure by now you’ve realized that most treasures in Chicago are actually hidden in plain sight – as evidenced by this archaeological museum!
Located on the University of Chicago campus, the Institute for the Study of Ancient Cultures features over 400,000 artifacts centered around ancient culture.
Set in a historical building, this museum boasts cultural artifacts from North Africa, West Asia, and the Middle East. Some of my personal favorites include an exhibit centered around the evolution of writing, artifacts from the Assyrian King Sargon II’s palace, and mathematical displays from Babylonian times.
After touring the museum, be sure to check out the Seminary Coop Bookstore, located just a few blocks away. Another hidden gem in the city, this independent bookstore dates back to 1961.
- Rating: 10/10 – Bucket List Essential
- Cost: Free
- Personal Opinion: Don’t miss it! A must-visit gem of excellence.
10. Escape the Crowds at the Library
If you’re wondering why I’m including a library (of all the things!) on this list of magical places in Chicago, wait until you see this place for yourself!
A serene oasis in the bustling downtown area, the Harold Washington Library is home to a secret architectural marvel known as the Winter Garden.
Located on the 9th floor of the library, this indoor garden boasts a glass ceiling and a vast, 3-storey atrium. Comfy seats, lush greenery, and the soothing gurgle of the water fountain only add to the sense of well-being that permeates the place.
If you ask me, this is the ideal place for relaxing after a full day of sightseeing! Oh, and did I mention that entry is entirely free of charge?
- Rating: 10/10 – Bucket List Essential
- Cost: Free
- Personal Opinion: Don’t miss it! A must-visit gem of excellence.
11. Keep your Eyes Peeled for the Chicago Municipal Device
Here’s another quirky aspect of Chicago that’s still relatively unknown to tourists – and forgotten by most Chicagoans!
First introduced in the late 1800s as part of a contest, the Municipal Device is basically a Y-shaped insignia designed to look like the branches of the Chicago River.
The symbol is practically everywhere in Chicago. I’m talking lampposts, railings, and various structures across the city. It’s even hidden in the facades of older historic buildings. Once you recognize the symbol though, you’ll start seeing it just about everywhere!
- Rating: 6/10 – Worth a Deeper Look
- Cost: Free
- Personal Opinion: There’s substance under the surface.
12. Challenge your Senses at the Museum of Illusions Chicago
Families, this one’s for you! Whether you’re looking for unique things to do in Chicago or simply want to keep the kids entertained, let me assure you that this is one underrated place that won’t disappoint!
With over 80 exhibits, the museum definitely has plenty to keep you entertained for a couple of hours. I’m talking mind-bending images, interactive installations, holograms, human-sized kaleidoscopes, and infinity rooms.
Plenty of eccentric souvenirs await at the onsite gift shop if you’d like to bring some brain puzzles back home! The museum sometimes hosts events, so be sure to check their website to see if there’s anything you’d like to participate in.
- Rating: 7/10 – Hidden Gem Alert
- Cost: Free
- Personal Opinion: Well worth the detour for a unique experience.
13. Explore the BAPS Shri Swaminarayan Mandir
If you don’t mind venturing off the beaten track, this is one hidden gem in Chicago that you really don’t want to skip!
An absolute sight to behold, this traditional Hindu temple is said to be the largest one in Illinois. Spanning across 30 acres, this temple is especially known for its intricate Indian architecture, complete with meticulously detailed pillars.
Made from 35,000 pieces of Indian Pink sandstone and Italian Carrara, the temple also features over a hundred archways, balconies, pinnacles, and two massive domes.
While this place is an absolute feast for the eyes, bear in mind that it’s a place of worship. As such, all visitors should remove their shoes before venturing inside and avoid shorts as well as sleeveless tops.
- Rating: 9/10 – Worth Bragging About
- Cost: Free
- Personal Opinion: An impressive find you’ll tell friends about.
14. Discover the Underground Tunnels
This is hands down the most thrilling must-do during your USA journey.
The underground tunnels of Chicago may be quite popular among the locals, but most first-time visitors don’t really know that there’s a whole world right under the city! I sure didn’t know about the tunnels until some local friends of mine took me underground.
Photo: Jaysin Trevino (Flickr)
If you’d like to properly uncover all the treasures concealed in this Chicago hideaway, I can vouch for this activity that’ll take you through the tunnels on a 2-hour tour.
Also known as the ‘Pedway’, the tunnels are home to hidden corridors and secret entrances leading to historic Government buildings and the Art Institute. Believe it or not, the Pedway even conceals underground swimming pools!
Your guide will also let you in on the secrets of the Loop that are hidden in plain sight. You’ll learn lesser-known trivia about the meaning behind ‘The Bean’ and even discover a cleverly concealed garden that most people can’t even see as they walk past it.
- Rating: 8/10 – Genuine Delight
- Cost: $35
- Personal Opinion: A true hidden gem, sure to make you smile.
15. Catch an Event at the Stan Mansion
Let’s wrap up our list of hidden gems in Chicago with a grandiose building that’s shrouded in a hefty dose of mystery!
One of the oldest historical buildings in the city, the Stan Mansion was originally built in 1923 to house the Humboldt Park Commandery No. 79. Dating back to the 18th century Crusades, this fraternal order is connected to the Freemasons.
This secret spot was eventually purchased by Cera Stan and turned into an event venue but rest assured that the mansion still holds plenty of its original splendor. This former Masonic Lodge often holds public events, giving you the chance to feast your eyes on its magnificent interior.
- Rating: 7/10 – Hidden Gem Alert
- Cost: This may involve occasional free community events.
- Personal Opinion: Well worth the detour for a unique experience.
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I can talk all day about these magical places in Chicago! But for now, here are some of the most commonly asked questions:
By now, I’m sure you’ve realized that Chicago leaves an indelible mark on anyone who visits it!
The Windy City is continuously reinventing itself so there’s always going to be something new for you to explore. From eccentric features like the Municipal Device to secret spots hidden in plain sight, this is one city that certainly caters to all types of travelers!
Feeling adventurous? Then you can always plan an epic backpacking trip across Chicago for a more immersive experience in this amazing city.
- Our ultimate backpacking Chicago guide is an essential read before you travel.
- Use our where to stay in Chicago guide to plan your adventure.
- Backpackers and frugal travelers can use our budget travel guide.
- Make sure you visit the other best places in the USA too.
- That will of course include many of the stunning National Parks of the USA.
- A great way to see the country is by taking an EPIC east coast road trip to add to your itinerary.
And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!
