Chicago
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Discover Another Side of Chicago With These 10 Hidden Gems + 5 Restaurants

Chicago is renowned for its iconic skyline and well-known landmarks like Wrigley Field, Willis Tower, and Navy Pier. But beyond the popular tourist spots and vibrant cultural scene, Chicago is also a city of hidden gems waiting to be discovered beyond the beaten path.

Chi-Town is a treasure trove for those willing to explore its nooks and crannies, from quaint parks bursting with local charm and lesser-known museums to quirky local shops. Whether you’re a lifelong resident or a first-time visitor, these hidden gems promise to showcase exciting parts of a bustling city that’s never short on amazement.

Promontory Point-Chicago
Promontory Point | photo via manavmeetstheworld

Promontory Point

Known to Chicagoans as The Point, this scenic man-made peninsula in Burnham Park juts out into Lake Michigan, inviting swimmers and sunbathers to enjoy the cool waters and beautiful views of the Chicago skyline.

While adventurers can swim at The Point year-round, the park is also the site of annual spring and fall swims to coincide with the summer solstice and autumn equinox.

Palmisano Park-Chicago
Palmisano Park | photo via bethisfit

Palmisano Park

Located in the heart of Chicago’s Bridgeport community, this 26-acre park has a little something for everyone. With nearly two miles of trails, a running track, an athletic field, and a fishing pond among other amenities, every visitor can find enjoyment here.

Nature enthusiasts can enjoy exploring interpretive wetlands and soaking in dramatic views from the top of a hill.

Visitors looking for some exercise can explore the park’s trails, which include boardwalks, concrete walks, and metal-grated walkways as they pass by ponds, wetlands, and preserved quarry walls.

Peggy Notebaert Nature Museum-Chicago
Peggy Notebaert Nature Museum | photo via upon.the.wildflowers

Peggy Notebaert Nature Museum

For decades, the Notebaert has played a unique role in the Windy City, connecting Chicagoans and visitors alike to nature with family events and unique exhibits.

That’s still true today as thousands of visitors come each year to explore the museum’s signature Butterfly Haven — with 1,000 free-flying butterflies — its Birds of Chicago exhibit, its nature trails, and fun temporary exhibits that showcase the beauty and uniqueness of nature.

International Museum of Surgical Science-Chicago
International Museum of Surgical Science | photo via diabhal.powerlift

International Museum of Surgical Science

Chicago has its fair share of fascinating museums, but the IMSS is an underrated gem. Across 10,000 square feet of space, visitors can stare in wonder at galleries dedicated to the history of surgery and ogle unique collections of artifacts and art related to medicine.

Woolly Mammoth Chicago
Woolly Mammoth Chicago | photo via jrcolvin123

Woolly Mammoth Chicago

The best hidden gems can sometimes be the most curious ones, and Woolly Mammoth has curiosities galore! Visitors can peruse the store’s collection of amusing and eclectic items that include maps, skeletons, books, bones, anatomy-related items, taxidermy animals, and more.

Surprises await around every corner and visitors can load up on cool Woolly bling during their time in the shop.

Graceland Cemetery-Chicago
Graceland Cemetery | photo via happy_pill_popper

Graceland Cemetery

You may not consider a cemetery to be a hidden gem. But this cemetery, established in 1860, is the burial site of many famous Chicagoans and several tombs of architectural interest.

It’s also a certified arboretum with more than 2,000 trees and includes a reflecting lake and winding pathways, making this a unique destination for even the most skeptical traveler.

Myopic Books-Chicago
Myopic Books | photo via 2024ninomi

Myopic Books

Sometimes the best adventures can be found in the pages of a book. At this Wicker Park bookstore, visitors of all ages can explore three floors of more than 60,000 new and gently-used books.

For over 30 years, Myopic has been a perfect spot to get lost in the wonderful world of books and every visitor can find at least one book to take home.

Merz Apothecary

Merz has been a staple on Chicago’s northside since 1875 and is an honest-to-goodness apothecary offering unique and natural products. People from around the world come to shop here from a selection that includes fragrances, skin creams, bath and body care, grooming products, and more.

Field Museum-Chicago
Field Museum | photo via kerouac

Field Museum

There’s plenty to see to fascinate your mind at the Field Museum, but Inside Ancient Egypt is one exhibit you won’t want to miss. Not only can visitors learn about the lives of Egyptians, but they can also see and enter a replica of an Egyptian tomb and see one of the largest collections of mummies in the United States.

Hancock Center-Chicago
Hancock Center | photo via uncletom_gbw

Hancock Center

Willis Tower is one of the most famous Chicago landmarks, offering views of Chicago from 1,353 feet. Hancock Center isn’t quite as tall, but it offers views of the Windy City from 1,030 feet on its 360 Chicago Observation Deck, allowing visitors to see the iconic Chicago skyline and Lake Michigan.

True adventurers can take their visit up another notch with the TILT experience, a special area where guests grab on to handlebars, lean forward and tilt out over the city. It’s available both day and night!

Guests can also visit the 94th floor of the tower and sip a cocktail at one of the highest bars in Chicago while soaking in incredible views of the city.

Calumet Fisheries-Chicago
Calumet Fisheries | photo via simiaosworld

5 Hidden Gem Eateries in Chicago

Calumet Fisheries

3259 E 95th St, Chicago, IL 60617

As one of the few remaining smokehouses in Illinois, visitors can come to nosh on one-of-a-kind smoked seafood delights. Calumet’s smoked offerings include catfish, shrimp, salmon, eel, and white fish along with full dinners and a la carte offerings, ensuring every seafood enthusiast can find their favorite dish.

Hop Leaf Brewery-Chicago
Hop Leaf Brewery | photo via lakesandlagers

Hop Leaf Brewery

5148 N Clark St, Chicago, IL 60640

Since 1992, Hop Leaf has been a beer pillar in Andersonville, offering beer, spirits, and cocktails in an environment designed to encourage camaraderie among friends. This adults-only venue is perfect for a night out with refreshing cocktails, beer, and tasty finger foods.

Waterfront Cafe

6219 N Sheridan Rd, Chicago, IL 60660

This hidden gem in Berger Park is perfect on a summer day. Visitors of all ages can soak in scenic views of Lake Michigan while enjoying a patio lunch with cocktails, beer, salads, and classic sandwiches. In the evening, the cafe is aglow in light as local musicians provide live entertainment. 

Taste of Lebanon-Chicago
Taste of Lebanon | photo via becca130

Taste of Lebanon

1509 W Foster Ave, Chicago, IL 60640

Not only does this Andersonville restaurant provide an authentic taste of Middle Eastern cuisine, but customers rave about its great value. Hungry visitors can step into this cozy environment and dig into flavorful favorites like falafel, shawarma, and tabbouleh.

The Dining Room at Kendall College-Chicago
The Dining Room at Kendall College | photo via i_reallly

The Dining Room at Kendall College

18 S Michigan Ave, Chicago, IL 60603

On the campus of Kendall College, visitors looking for a fine dining experience can come here for a delicious meal and fantastic views of the Chicago skyline. Hospitality management and culinary arts students prepare exquisite meals in this classroom/dining room and gratuities go toward scholarships at the school.

Exploring Exciting Hidden Gems in Chicago

If you’ve already seen every tourist spot in Chicago, explore another side of the Windy City at some of its best hidden gems. Whether you’re looking for the perfect swimming spot on Lake Michigan, a new favorite eatery, or a new museum to explore, Chicago has many surprises awaiting curious travelers to come and discover.