6 Amazing Rooftops in Chicago that You Can Actually Rent on Peerspace

Chicago is a beautiful city year-round — though it’s sometimes difficult to fully appreciate the sights during the frigid winter months. When the temperature heats up, Midwesterners turn out in droves to take advantage of the sunshine and warmth. What better way to soak up the summer sun than on one of the best rooftops in Chicago? Take a look at these must-see rooftop terraces, all available on Peerspace.

1. This incredible rooftop with a view in Lake View

Located in Lakeview just blocks from Wrigley Field and Lake Michigan, this large “Sky Deck” is ideal for a big event. It comprises 3,000 sq. ft. of flexible open space that can be arranged to suit a seated dinner, cocktail party, or even a dance floor. Depending on the furniture configuration, capacity can range from 150 to 300 people.

Glass railings provide an unobstructed 360-degree view of the city and lake. The space includes umbrellas, lounge furniture, a gas grill, two bars, plus a microphone and speaker system. An elevator makes it highly accessible. There’s also a meeting room available in the building below; this is a great venue for a conference by day, party by night.

2.  This rooftop event space, complete with prairie grass

This modern, minimalist space in Noble Square provides a unique combination of cityscape and countryside. Sliding glass doors to both the north and south open wide to create a flow-through indoor/outdoor space with views of the surrounding city. At 1,500 sq. ft., this spot can accommodate up to 90 people standing, and it’s equipped with tech like an 84” TV, as well as ab Apple TV and video-conferencing tools, including a camera and mic.

The outstanding detail about this space: the prairie ecosystem. Native grasses and wildflowers grow on the roof, providing a much-needed touch of green in this concrete landscape.

There are live bees on another part of the roof to help the prairie thrive, so make sure to take note of any allergies! This place functions as both a dedication to sustainability and a one-of-a-kind homage to the Midwest, making this one of the best rooftops in Chicago.

3. This funky, “maximalist” playhouse

Minimalism may be “in,” but this townhouse in Humboldt Park is proving that there’s still a place for color. The interior is bright and eclectic with hot pink accents and unique pop art in every room. Custom decor like colorful wall murals and acrylic deer heads add to the playful vibe.

Up on the roof deck, the colors continue with custom graffiti and even a tiny patch of grass. Lounge chairs invite you to sunbathe with a cocktail, and you can even peek in on one of the rooms below through the skylight.

You could spend a lot of time wandering around this space, taking in all the custom art and decor. With so much to see, it’s no wonder this townhouse and roof deck has appeared in photoshoots, music videos, and on HGTV.

4. This historic hotel‘s gorgeous rooftop

This gorgeous space on the 26th floor of the Virgin Hotel in The Loop has so-close-you-could-touch-it views of downtown Chicago. Famous buildings, including Marina City (the two towers that look like corn cobs), Trump Tower, and the Jewelers’ Building, place you firmly in the Windy City.

The wrap-around roof deck with its birds-eye view of the cityscape has tables and chairs to comfortably seat 60 attendees. Inside the Trophy Room, modern lounge furniture and some eclectic decor (i.e., wall mounted beetles) create a unique space you won’t find anywhere else.

The central location means that public transportation to and from this rooftop will be easy for guests. Although since it’s in a hotel, some may just want to stay the night!

5. This spectacular rooftop space

Not all of the best rooftops in Chicago have magnificent views. Some may cause you to forget that you’re in one of the largest metropolitan areas in the country. This relaxing retreat in Logan Square is nestled among ivy-covered brick walls, creating a quiet oasis in the middle of the city. With shaded cabanas and umbrellas, it’s a fabulous place to enjoy a sunny summer afternoon.

There is plenty of comfy lounge furniture, plus a bar and gas grill, making this a great option for a cookout with up to 50 friends or coworkers.  The owners request no bachelor/bachelorette parties or weddings, but a baby shower or surprise party would be ideal!

6. This unique rooftop farm

The West Town area of Chicago is full of art galleries, independent theaters, and small music venues. Tucked away in this hip neighborhood is a vibrant loft space with a rooftop deck. The loft features a full kitchen and large windows to let in plenty of natural light.

Outside on the deck, there are skyline views under a thriving rooftop farm. Fresh produce and flowers from the garden area are even available for your event upon request. With its combination of indoor and outdoor spaces, this spot would be the perfect venue for events like a conference or workshop for up to 80 people, followed by a cocktail party under the cafe lights.

Find a rooftop venue in Chicago on Peerspace