Summer in Chicago is hard to beat, and there’s no better place to enjoy it than from a rooftop pool with the skyline in the background. As new luxury apartment buildings continue to open across downtown, developers have turned rooftop amenity decks into true extensions of residents’ living spaces. Infinity edge pools, private cabanas, outdoor kitchens, fire pits, and sweeping views have become just as important as the apartments themselves.
If a rooftop pool is at the top of your wish list, these luxury apartment buildings offer some of the best outdoor pools in the city!
1000M
South Loop
Designed by renowned architect Helmut Jahn, 1000M has one of the most recognizable skylines in Chicago, and the rooftop amenity deck lives up to the building’s reputation. The pool overlooks Grant Park and Lake Michigan, giving residents uninterrupted views that stretch from the museum campus to the downtown skyline.
The building also includes a full wellness center, indoor and outdoor lounges, spa amenities, and thoughtfully designed common spaces that make it easy to spend an afternoon without leaving home.
One Chicago
River North
One Chicago delivers one of the most complete amenity packages in the city. The outdoor pool terrace is surrounded by seating, landscaped gathering spaces, and skyline views, making it one of the building’s most popular features during the summer.
Residents also have access to a large fitness center via Lifetime Fitness, coworking lounges, sports simulator, and direct access to Whole Foods Market, all without leaving the property.
111 Point
River North
As one of River North’s newest luxury apartment communities, 111 Point brings modern design and elevated amenities to one of Chicago’s most walkable neighborhoods.
The rooftop pool offers plenty of space to relax, while the surrounding terrace creates an inviting setting for spending time outdoors. Inside the building residents will find coworking spaces, a state of the art fitness center, entertainment lounges, and beautifully designed interiors just steps from the Chicago Riverwalk and River North’s restaurant scene.
Cassidy on Canal
Fulton Market
Positioned between Fulton Market and River North (technically the Fulton River District), Cassidy on Canal pairs contemporary apartments with an outdoor amenity deck designed for entertaining. The rooftop pool is surrounded by lounge seating, grilling stations, and gathering spaces that take full advantage of Chicago’s summer months.
Its location also places residents within walking distance of Randolph Street, East Bank Club, Merchandise Mart, and the Riverwalk.
Optima Signature
Streeterville
Few apartment buildings offer as much as Optima Signature. The rooftop pool features panoramic views of both Lake Michigan and the downtown skyline, while an extensive list of amenities keeps residents busy year round.
In addition to the outdoor pool, the building includes an indoor pool, pickleball and basketball courts, a golf simulator, multiple fitness spaces, coworking lounges, and beautifully appointed resident areas. It’s one of the most amenity rich buildings in Chicago.
NEMA Chicago
South Loop
NEMA Chicago is known for both its architecture and its expansive amenity collection. The outdoor pool deck is one of the highlights, offering skyline views, comfortable seating, and plenty of room to unwind.
Residents also enjoy outdoor kitchens, fire pits, wellness facilities, sports courts, and social spaces inspired by high end hotels, making the building feel like a private club.
Cascade
Lakeshore East
Located in Lakeshore East, Cascade offers a quieter rooftop experience with views of the Chicago River, Lakefront, nearby parks, and the surrounding skyline. The pool deck provides a relaxing escape while remaining just a short walk from the heart of downtown. Additional amenities include a fitness center, resident lounges, coworking spaces, and entertainment areas that complement the building’s modern design.
Find a Chicago Apartment You’ll Love Year Round
A rooftop pool might be what first catches your attention, but the right apartment is about finding a building that fits your lifestyle, commute, and neighborhood preferences. If you’re moving to downtown Chicago, whether you’re considering River North, Streeterville, Fulton Market, Lakeshore East, or the South Loop, Downtown Apartment Collective can help you compare Chicago’s top luxury apartment buildings, current pricing, and available move in specials to find the right fit.
