When summer finally arrives, Chicagoans enjoy spending as much time as they can outdoors. Whether it’s hanging out at a restaurant or bar patio, biking on the lakefront, or attending the many seasonal festivals and events, this city knows how to make the most of the warmer weather. What is another great way city dwellers can reap the benefits of summer living? The urban lifestyle pairs perfectly with a rooftop deck, providing some kind of outdoor space (which isn’t always guaranteed with a city home) while soaking in all the sights and sounds found in a place like Chicago. Not only can they be used for parties, gardening, and relaxation, but a rooftop deck is also a great overall investment for your property. As you will see with the following condos for sale, it’s important to have a space that people actually want to spend time in, with varying degrees of enclosure to offer some privacy from nearby neighbors while also maintaining a balanced design. Plus, there is a movie connection: The first property below was featured in the film High Fidelity (you might remember the scene where the main character, Rob, reconnects with his ex-girlfriend, Charlie, at a dinner party). 

2250 W Ohio St APT 304, $1,280,000

In Chicago’s West Town, the historic Bodine Building was originally built in 1920 as a factory to manufacture electric motors. By 1995, the three-story brick structure with an interior courtyard had been converted into 20 residential units. This 4,000-square-foot top-floor duplex comes with an original 35-foot-wide skylight, flooding the entire loft with natural light. The property has three bedrooms, two-and-a-half bathrooms, and two separate rooftop decks with amazing views of the downtown skyline. IPE wood decking covers this private outdoor area more than 1,000 square feet, which includes an outdoor kitchen. 

1327 N Dearborn St #3, $1,099,000

What’s at the top of this historic Italianate three-flat, originally constructed in 1886 and located on one of the prettiest streets in the Gold Coast? An updated two-bedroom, two-bathroom condo that features a superb outdoor space. The recently completed rooftop deck boasts an outdoor kitchen, lighting, new trellises, composite decking, and a turfed area. Because of the luxury and walkability of the neighborhood, it is no surprise that the asking price is quite high for only 1,800 square feet of interior space (with additional $750 monthly HOA fees).

1354 N Campbell Ave #3, $525,000

Directly east of Humboldt Park in West Town is a two-bedroom, two-bathroom penthouse that includes a private, partially covered rooftop deck spanning the entire length of the building. Inside the unit is a floating staircase that takes you right up to the roof, which features a custom-built pergola, gray trex composite decking, and colorful murals. There is also a front and back balcony. It last sold a decade ago for $310,000, so the asking price is now over 69% higher. But when you consider the buyer gets three outdoor spaces in a gentrifying part of the city, I’d say the price is still quite affordable (with only $182 monthly HOA fees). 

400 S Green St APT 556, $1,150,000

This next property might be at a disadvantage (it’s located next to Interstate 290) but the West Loop is still a very desirable location for many buyers out there. Originally built as an industrial warehouse in 1895, the building was converted into Green Street Lofts in the mid-1980s. It maintained its historic features, including large windows, exposed brick, and timber ceilings. This 2,779-square-foot, two-bedroom, two-bathroom corner penthouse with north and west exposures has an incredible 540-square-foot rooftop deck. Plus, it’s easily walkable to Mary Bartelme Park, the Blue Line, and everything this area has to offer. 

215 W Illinois St APT 6B, $1,750,000

I’m sure many people dream of living in a place like this multi-level penthouse located in the 18-unit Anchor Lofts, originally constructed in 1925 in River North. Spacious and open with plenty of updates, the 3,000-square-foot condo features two bedrooms, a chef’s kitchen, a full walk-in closet off the primary bedroom, and lots of glass doors separating the floor plan. The flexible second level has more glass doors that open to the 1,000-square-foot rooftop terrace. The definition of downtown city living, the deck includes a hot tub, custom mural, outdoor television, fire pit, and covered sitting area.