Chicago summers are legendary, but when late July hits and the humidity radiates off the downtown concrete, you need a place to cool off. Surprisingly, finding a hotel with an actual outdoor rooftop pool in this city is incredibly rare.
Of course, you don’t need a rooftop pool to have an amazing trip. If you just want a phenomenal room and don’t care about swimming, you can check out the highest-rated Chicago hotels right here.
But if you want the ultimate summer oasis, we’ve done the scouting for you. From ultra-exclusive West Loop hangouts to massive urban resorts, here are the 8 best Chicago hotels with rooftop pools for your summer getaway.
1. Viceroy Chicago (Gold Coast)
If you want to feel like royalty during your Chicago stay, you book a room at the Viceroy. Located in the swanky Gold Coast neighborhood just minutes from the Magnificent Mile, this property offers a top-tier luxury experience.
Set 18 stories above the busy streets, the seasonal rooftop pool is an absolute stunner. After a refreshing dip with panoramic views of Lake Michigan, you can dry off and walk just a few steps over to Devereaux, the hotel’s stylish rooftop cocktail lounge, for some poolside oysters and a spritz. It doesn’t get much more glamorous than this.
Useful Info & Tips:
- Exclusive Access: The pool is strictly reserved for hotel guests, meaning you won’t have to fight massive crowds to secure a sun lounger.
- Food & Drink: You can order top-tier cocktails and light bites directly to your chair from the attached Devereaux lounge.
- Location Perk: You are only a few blocks away from Oak Street Beach and the high-end shopping of Michigan Avenue.
2. The Hoxton (West Loop / Fulton Market)
The West Loop is Chicago’s undisputed dining capital, and The Hoxton sits right in the beating heart of it. Known for its gorgeous, mid-century modern design and welcoming “open-house” lobby, the hotel saves its best feature for the very top floor.
The rooftop pool here gives you a stunning, unobstructed view of the downtown skyline from the west. But the real perk of swimming here? The pool shares the roof with Cabra, celebrity chef Stephanie Izard’s vibrant Peruvian restaurant.
Useful Info & Tips:
- The Menu: Your poolside lounging comes with an elite menu of ceviche, empanadas, and dangerously good Pisco Sours from Cabra.
- The Crowd: The Hoxton draws a very trendy, young professional, and creative crowd.
- Neighborhood: You are walking distance from “Restaurant Row,” making this the absolute best hotel choice for hardcore foodies.
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3. Soho House Chicago (West Loop)
Housed inside a beautifully restored former belting factory in Fulton Market, Soho House Chicago is the ultimate “see and be seen” destination. This rooftop pool breathes pure exclusivity.
Because it operates as a private members’ club, you absolutely cannot just walk in off the street to grab a towel. However, booking a hotel room grants you temporary access to the club’s incredible amenities, including this sun-drenched, ultra-chic rooftop oasis.
Useful Info & Tips:
- How to Get In: You must be a Soho House member or a registered hotel guest to get past the velvet rope to the pool.
- House Rules: Soho House has a notoriously strict “no photos” policy in its club spaces to protect the privacy of its guests. Put your phone away and just enjoy the vibe!
- Amenities: The rooftop features cozy fireplaces and incredibly plush loungers for chilly Chicago evenings.
4. The Robey (Wicker Park)
If you want to escape the downtown tourist bubble, head northwest to Wicker Park. The Robey is a beautiful, 1920s Art Deco masterpiece that towers over the bustling six-way intersection of Milwaukee, Damen, and North Avenues.
Up on the 6th floor, you’ll find a stunning, triangle-shaped outdoor pool. Because it’s located outside of the downtown core, you get an incredible 180-degree view looking back at the Chicago skyline.
Useful Info & Tips:
- The Setup: The pool is exclusively for hotel guests, but it shares the 6th-floor space with Cabana Club, a breezy indoor/outdoor cocktail bar that is open to the public.
- Pro-Tip: If you want a quiet, relaxing swim, get out there early in the morning before the rooftop bar opens for the day.
- The View: This is arguably one of the most unique skyline views in the city, perfect for sunset watching.
5. Radisson Blu Aqua Hotel (Lakeshore East)
If you are looking for a massive urban resort right in the middle of the city, the Radisson Blu Aqua Hotel is your answer.
Famous for its wavy, undulating exterior balconies, the building houses an absolutely massive rooftop recreation deck. Instead of just a tiny plunge pool, the Radisson offers a 25-meter lap pool where you can actually get some strokes in, all while being perfectly nestled among the towering skyscrapers of Lakeshore East.
Useful Info & Tips:
- Massive Space: The sun deck is one of the largest in Chicago, meaning there is almost always a chair available.
- Extra Amenities: Beyond the pool, the outdoor deck also features hot tubs, fire pits, cabanas, and a running track.
- Family Friendly: Because of the sheer size and variety of amenities, this is a fantastic option if you are traveling with kids.
6. DoubleTree by Hilton Magnificent Mile (Streeterville)
Sometimes, location is everything. Situated just two blocks off of Michigan Avenue, the DoubleTree Magnificent Mile is the ultimate convenience stay.
After a sticky, hot day of walking the city and shopping the avenue, there is nothing better than dropping your bags in your room and immediately heading up to their newly renovated rooftop pool. Surrounded by the dense architecture of Streeterville, you truly get the feeling of swimming right in the middle of a concrete canyon.
Useful Info & Tips:
- Recent Upgrades: The pool and terrace deck were recently renovated, offering modern, comfortable sun loungers and umbrellas.
- Location, Location: You are a five-minute walk from Navy Pier, the Starbucks Reserve Roastery, and the Mag Mile.
- Accessibility: An excellent, straightforward, and reliable hotel option for families or groups who want to be right in the middle of the tourist action.
7. The Penthouse at Grand Plaza (River North)
If you are traveling with a larger group or just want to explore Chicago in style, the Penthouse at Grand Plaza is a phenomenal choice.
Unlike a traditional hotel, this property offers luxury penthouse condos and vacation rentals right in the heart of River North—Chicago’s premier nightlife and dining district. The building’s massive, seasonal outdoor pool is surrounded by a sprawling sun deck where you can swim directly among the towering River North skyscrapers. It is an absolute oasis in the middle of one of the city’s busiest neighborhoods.
Useful Info & Tips:
- Aparthotel Perks: Because these are penthouse condos, you get apartment-style living (full kitchens, massive living spaces) with resort-style amenities, making it perfect for bachelor/bachelorette parties or large family trips.
- Mega Amenities: The pool deck isn’t the only perk; the facility also boasts a running track, a basketball court, and saunas.
- Nightlife Ready: You are within walking distance of Chicago’s best clubs, late-night bars, and high-end steakhouses.
8. Holiday Inn Hotel & Suites Chicago – Downtown (South Loop)
Having a rooftop pool in Chicago doesn’t always have to come with an ultra-luxury price tag. Located just a few blocks away from the iconic Willis Tower (formerly the Sears Tower), this Holiday Inn is the perfect choice if you want a great mix of comfort, location, and value-for-money.
While it might not have the swanky cabanas or velvet ropes of the West Loop spots, the seasonal outdoor rooftop swimming pool is spacious, relaxing, and offers great cityscape views. It is a genuine blessing after a long day of sightseeing in the July heat.
Useful Info & Tips:
- Budget-Friendly: This is arguably the most affordable way to get access to a private, elevated outdoor pool in downtown Chicago.
- Privacy & Peace: Because it isn’t attached to a massive day-club or trendy rooftop bar, this pool tends to offer a bit more peace, quiet, and privacy for guests.
- Transit Access: It’s located very close to Union Station and the CTA Blue Line, making getting around the city a breeze.
Things To Know Before You Go
Before you pack your swimsuits and book your flights, keep these quick local tips in mind:
Mind the Seasons: Chicago winters are no joke. Outdoor hotel pools in the city are strictly seasonal. While exact dates vary by property based on the weather, expect these pools to be open exclusively from Memorial Day weekend through Labor Day weekend.
The “Windy City” Factor: Even on a 90-degree day in July, the wind coming off Lake Michigan can feel chilly when you are 18 stories up in a wet bathing suit. Always bring an extra towel or a cover-up to the roof!
Book Early: Summer is Chicago’s peak tourism season. Because hotels with outdoor pools are so rare here, they sell out incredibly fast. If you are planning a summer trip, book your room months in advance.
Which of these rooftop pools are you hitting first? Let us know in the comments below!
