Our Favorite Outdoor Spaces We've Sold: Rooftops, Patios & Hidden Gems from Our Past Chicago Sales
- The Editorial Team
- Jul 17
- 3 min read
There’s nothing like summer in Chicago—especially when you’ve got the perfect outdoor space to enjoy it. From rooftop decks made for sunset cocktails to patios that feel like your own private oasis, these past listings had some seriously standout spots. Our Realtor Laura Davis rounded up her favorite rooftops, patios, and backyard escapes to inspire your next outdoor hang. Looking to upgrade your outdoor space? Check out some of our current listings here!
This Old Town listing has direct access to a huge private terrace with endless possibilities to customize into the ultimate lounge or entertaining space. The bright and airy rooftop deck delivers modern lounge vibes with sleek furniture and space for both dining and relaxing. It’s the perfect city perch for sunny afternoons and starlit dinner parties. See more of this unit here and then take a look at the penthouse unit we sold in the same building here - the views were JAW DROPPING.
This fun and functional private rooftop deck in Lake View is the ultimate entertaining spot—fully landscaped and outfitted with bold striped seating, a shaded pergola, built-in cabinetry, a TV, wet/dry bar with fridge, and a long picnic-style table. With skyline views and space to lounge or host, it’s made for unforgettable gatherings. The rooftop of this unit was spectacular but you also have to see inside this highly decorated home here.
Minimalist style meets maximum skyline views on this sophisticated rooftop in Lincoln Park. A modern fire feature and classic wicker lounge set make it perfect for everything from morning reads to sunset happy hours. This home came with several other outdoor areas including a children's play area over the garage. You can see all of them here.
If you're looking for outdoor entertaining space inspiration, look no further. This PRIVATE 2000 sq ft terrace in Lake View designed by Topiarius has been awarded top honor (Gold Award) for residential design by the IL Landscape Contractors Association. Tucked under a series of elegant garden arches, this lush and private seating area is straight out of a storybook. See more of this beautiful duplex condo here.
This beautifully designed rooftop deck checks every box: fire pit, pergola, dining area, and even turf for lounging. Surrounded by spring blossoms in Bucktown, it’s a dreamy extension of the home—perfect for gatherings big or small. See inside the home here.
Perched high with unbeatable views of the Chicago skyline, this rooftop stunner in Ukrainian Village features a fire pit, a hot tub, and spacious seating—making it the go-to spot for soaking up summer days or unwinding under the stars. See here for more of this fine home.
Rain or shine, this covered patio is ready to host. The pergola is equipped with five built-in heaters, while a gas line to the Weber grill ensures you never run out of fuel during cookouts. With cozy sectional seating, and a grill station, it’s designed for year-round comfort and effortless backyard entertaining. Click here to see the rest of the yard which also featured a sauna and a fire-pit!
This shared backyard space for this Logan Square multi-unit building is a stunner with a spacious deck, lounge furniture, and soothing landscaping. Effortlessly charming with its natural wood deck, garden edges, and string lights, this space proves you don’t need much to create a backyard hangout that feels like a warm-weather retreat. When we sold this building it was currently set up as a cash-flowing Airbnb. See inside all the units here.
Whether you’re dreaming of skyline views, garden hideaways, or the perfect place to grill and chill, these outdoor spaces prove that the right setup can turn any home into a summer sanctuary. Ready to find your own slice of outdoor bliss? Reach out to Laura Davis to start the search—or to simply swap patio inspo over coffee.
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