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10 Awesome Hidden Gems in Chicago

Chicago is known for a few things: sports teams, deep-dish pizza, and cold, snowy winters. But if you’ve come to the Windy City looking for something less familiar, we’ve put together this list of hidden gems in Chicago to help you out. From pedestrian tunnels in the Loop, to private event spaces you can rent for a party or photoshoot, these 10 places will give you a different perspective on the city than you’d find on a typical tour. Whichever of these hidden gems you visit, you’ll walk away with memories of a fun adventure, as well as plenty of pictures for your Instagram feed!

1. The Chicago Pedway

Although not as famous as Montreal’s Underground City, Chicago’s Pedway is a similar network of pedestrian tunnels, bridges, and covered walkways that can help you avoid the cold weather. You’ll find a range of shops and restaurants covering 40 city blocks, including cool architecture and even art installations. Explore it on your own, or take a tour to learn more about its history.

2. A French chateau-style mansion on the North Side

1916-era french chateau chicago rental
Source: Peerspace

Among the city’s architectural treasures is this hidden gem in Chicago’s North Side. It was built in 1916 and is now a registered Chicago landmark. You can rent it by the hour for a photoshoot, dinner party, or small gathering of up to 85 people. Some of its features include fireplaces, stone walls, marble staircases, hardwood floors, and stained glass windows. With its antique furniture, bookshelves and portraits lining the walls, you’ll have several rooms to choose from — and over 5,000 sq.ft. — in which to host your event or photoshoot.

3. A red-themed speakeasy in Wicker Park

Speakeasy in Wicker Park chicago rental
Source: Peerspace

This speakeasy-themed event space will bring you back to Prohibition-era Chicago, with its red brick walls, stylish chairs and couches, and even a piano! One of the highlights of this space is its A/V equipment, which includes a digital video projector, microphone, and sound system. It’s perfect for hosting an underground movie screening, musical performance, or birthday party. Catering is available directly from the host or through the Peerspace Concierge service.

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4. Myopic Books

Myopic Books is proof that independent bookstores are here to stay, with over 70,000 books on the shelves, and live music performances and poetry readings to give you something to do on a chilly evening. Browse the shelves, or bring your own used books to resell. Photos and phones aren’t allowed, though, so if you’re looking for great shots for you Instagram feed, you’ll have to content yourself with pictures of the exterior!

5. A self-pour tasting bar in Wicker Park

Self-Pour Tasting Bar in Wicker Park chicago rental
Source: Peerspace

This self-serve tasting bar takes a simple premise — pouring your own drinks — and turns it into an experience. The idea is that you can sample small glasses of each drink, rather than having to order a full pint. You get an electronic card that tallies up what you drink and you pay on the way out (or it’s added to your minimum spend if you’re hosting an event). This is a fun idea for birthday parties, after work outings, and other group events. There are non-alcoholic options on tap, too — including kombucha, craft soda, cold-brew coffee, and more — so no one’s left out!

6. The Gene Siskel Film Center

As half of Chicago’s famous movie review team, Siskel and Ebert, Gene Siskel influenced the way an entire generation went to the movies. You can continue to be inspired by his dedication to cinema at the Gene Siskel Film Center, which hosts film festivals and independent features, as well as private screenings year round. You can rent out the facilities for meetings, birthday parties, school groups, and more, with a capacity of 63 or 196 for a private screening.

7. An artsy rock climbing gym in West Loop

Exciting Rock Climbing chicago rental
Source: Peerspace

This colorful rock climbing gym is suitable for more than just a climbing session. With room for up to 500 guests, this massive 25,000 sq.ft. space can be rented out for musical performances, yoga classes, parties, and more. While you can arrange for catering and bartending through the Peerspace Concierge, keep in mind that alcohol isn’t allowed until you’re finished climbing.

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8. A vibrant community space in West Town

A Unique Intimate Haven Amid Local Literature Media chicago rental
Source: Peerspace

This cozy venue is a hub for Chicago’s creative scene, and is home to an “experimental library” that’s devoted to local zines, comics, newspapers, and more. It has a sound system, projector, tables and chairs, a small stage, and a fireplace. There’s also a back porch and yard, a kitchen that can be used for catering, and a wheelchair-accessible restroom. Recent guests have used it to host a book launch and an intimate wedding. It can accommodate up to 99 people at once, depending on seating arrangements, making this a cozy hidden gem in Chicago.

9. A scientific museum on Lake Michigan

scientific museum historic mansion chicago rental
Source: Peerspace

This historic mansion is a Chicago landmark, and one of the few houses of its kind on the lake. A public museum by day, by night it becomes a multi-purpose event space, and is available for cocktail parties, weddings, seated dinners, and more. Built in 1917 and modeled after a chateau in Versailles, this is truly one of the top hidden gems in Chicago. You’ll have access to all of the museum’s four floors, including eight stone fireplaces, a gilded staircase, and more. Catering and furniture rentals are available for an additional fee from a list of approved vendors.

10. A converted church in Logan Square

Converted Circus Church in the heart of Logan Square chicago rental
Source: Peerspace

This former church has been turned into a vibrant circus venue, and is the perfect place to enjoy an artsy night out in Chicago. The venue has been rigged for aerial and acrobatic performances, although only in-house performers are allowed, so you’ll have to coordinate with your host for a booking. It can serve as an event space for a birthday party, wedding, corporate outing, or any other event that you can think of, for up to 100 seated guests or 300 standing.

As with many major cities, there’s more here than meets the eye. We think you’ll enjoy these 10 hidden gems in Chicago that are suitable for a variety of occasions, from parties to photoshoots to fun urban outings. For even more ideas, browse the listings on Peerspace to find a venue that can accommodate a small group, a large crowd, and anything in between!

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