There are more Chicago hotels with rooftop pools than most big cities in the country, so it’s important you choose wisely which one you’d like to stay in.
Some of the best hotels with rooftop pools Chicago can offer are in the middle of the city with nothing but skyscraper views, and others have a view of the beautiful Lake Michigan or views of the skyline from Midtown. Some are on the 30th floor, and others are on a modest 6th but with great vibes.
Below is a comprehensive outline of all the best rooftop pool hotels in Chicago with all the info you will need to decide which one to stay at. Happy rooftop hunting!
BEST HOTELS WITH ROOFTOP POOLS IN CHICAGO
- Best Chicago hotel with rooftop pool for views + groups: The Penthouse at Grand Plaza
- Best Chicago hotel with rooftop pool for couples: The Viceroy
- Best Chicago hotel with rooftop pool for pool bar + party vibes: The Hoxton
- Best Chicago hotel with rooftop pool for families: Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
- Best Chicago hotel with rooftop pool for quiet/relaxation: Kasa Chicago Old Town
- Best Chicago hotel with rooftop pool AND restaurant: The Robey
Best Downtown Chicago Hotels with Rooftop Pools
Here are the best hotels with rooftop pools in downtown Chicago, from the Magnificant Mile to the Millenium Park to Union Station to Fulham Market to Old Town. These are the most central hotels; many of them are very high-rise and have absolutely EPIC rooftop pool views.
The Viceroy Chicago
The Hotel: The Viceroy Chicago is one of the city’s most popular 5-star hotels. Located a few minutes from the top end of the Magnificent Mile and about 10 minutes from the shore, this is one of the northernmost Chicago hotels with a rooftop pool.
The Rooms: The Viceroy has a wide range of rooms from the basic ‘superior room’ to the penthouse. We recommend booking a Lake View Suite or Grand Room for the BEST view.
The Rooftop Pool: The Viceroy Rooftop Pool can be found overlooking the rest of the Magnificent Mile on the 18th floor. It’s surrounded by a snaking glass wall with plenty of deck chairs and also tables to sit and relax at or stand at during the night. You can also find the classy cocktail bar ‘Devereaux’ here.
Hotel Location: Gold Coast Neighborhood Chicago
How to Access the Rooftop Pool: Stay at the Hotel or Visit the Devereaux Bar from 5pm Wednesday-Sunday.
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
The Penthouse at Grand Plaza
The Hotel: Technically an ‘aparthotel,’ The Penthouse at Grand Plaza is comprised of nine penthouses with one, two, or three bedrooms. Each offers gorgeous living spaces and floor-to-ceiling glass windows overlooking the city and Lake Michigan on the 50-51st floor.
The Rooms: Perfect for couples, families, or groups, this would be the best bet for people who will need more than one room and love a good view. The spaces are large and open with beautiful design and natural light. Most have balconies as well.
The Rooftop Pool: This Chicago Hotel with Rooftop Pool is unbeatable. Shared amongst the 9 units is a HUGE rooftop pool, running track, fitness, center, and more. The rooftop pool is fairly huge and fits dozens of sunchairs around it with gardens too. The view is amazing with skyscrapers all around but plenty of sun.
Hotel Location: N State Street Chicago Above Grand Station
How to Access the Rooftop Pool: Must be a Hotel/Building Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
The Hotel: Homewood Suites by Hilton Chicago Downtown/Magnificent Mile is one of 3 Homewood Suites in the city, but the only one with a rooftop pool so make sure not to confuse them!
Located RIGHT on the Magnificent Mile of Michigan St, you can’t go wrong with this location. The hotel itself is basic but comes equipped with all the amenities you will need.
The Rooms: This one of the only hotels on this list with suites and 1BR apartments with a full kitchen, making it one of the best options for those who want a Chicago hotel with rooftop pool but also want to cook at the room.
The Rooftop Pool: The Rooftop Pool at Homewood Suites is on the fully-enclosed rooftop with glass windows to block the wind. It’s small yet large enough to get some sun while in the water, and is surrounded by plenty of deck chairs to lay out and get a tan.
Hotel Location: Magnificent Mile Near the Contemporary Art Museum (Near North)
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Hampton Inn Chicago Downtown/Magnificent Mile
The Hotel: The Hampton Inn is located in the exact same building as the Homewood Suites above, but with a different part of the building. The difference is that Homewood is suited with a kitchen and Hampton is regular, cheaper hotel rooms.
The Rooms: These are basic budget hotel rooms which also offer fantastic views of Chicago and Lake Michigan. This is a great choice if you want a more affordable room still with great views.
The Rooftop Pool: Same as the one described above, the Hampton Inn rooftop pool is an enclosed 40th floor space offering amazing views of Lake Michigan, deck chairs, and wind-breaking windows.
Hotel Location: Magnificent Mile Near the Contemporary Art Museum (Near North)
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
DoubleTree By Hilton Downtown Magnificent Mile
The Hotel: Located off the Magnificent Mile just 2 blocks from Navy Pier, the DoubleTree by Hilton Downtown Chicago is a well-equipped mid-range hotel in a great location. It has a restaurant on-site as well as one of the most spacious rooftops on this list!
The Rooms: You can stay in a variety of rooms from a basic to a fitness room to a deluxe suite. The rooms have great amenities and often great views also – all with flat-screen TV’s. For the price this Chicago hotel with a rooftop pool might have the BEST value.
The Rooftop Pool: The DoubleTree Rooftop Pool has views in every direction and an interesting round-ish shape. It’s one of the most spacious rooftop pool hotels in Chicago, with plenty of deck chairs, seating, and shade. You’ll feel like you’re surrounded by Chicago with buildings shooting up in all directions around you!
Hotel Location: Between the Magnificent Mile and Navy Pier (Near North)
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
LEVEL Chicago Old Town
The Hotel: One of the lesser-known Chicago hotels with rooftop pools, LEVEL Chicago Old Town is a complex comprised of different sizes of apartments for rent from studio to 2-Bedroom Corner Suite. Theres also a spa and wellness center available to guests.
The Rooms: LEVEL old town features 60 apartments of different sizes that all feature full kitchens, flatscreen TVs, amazing views, and Air Conditioning.
The Rooftop Pool: The rooftop pool is a long and thin pool on a mid-level of the building, surrounded by lounge beds and deck chairs. The rooftop is also equipped with a half basketball court, a sauna and steamroom, a fitness center, and even BBQ grills, making it perfect for a group getaway!
Hotel Location: Near North: between Gold Coast + Old Town – Near Clark/Division Station
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Radisson Blu Aqua Hotel
The Hotel: The Radisson Blu Aqua Hotel is one of Chicago’s most impressive hotels. Designed by a famous architect, you’ll be amazed by the interestingly shaped ripples that flow throughout the skyscraper.
The AquaHotel has an on-site restaurant, an elegant lobby, and the perfect location between Millenium Park and the Chicago River.
The Rooms: The rooms are well-equipped with expected hotel amenities. They all have balconies, impressive Chicago views, TV’s, toiletries, etc.
The Rooftop Pool: The Radisson Blu Aqua Hotel probably has the most impressive rooftop pool complex on this list of Chicago hotels with rooftop pools. Not only does it have a full 25m Olympic lap pool, but it also features a sauna, outdoor track, another indoor pool, sun cabanas, hot tub, fire pit, gardens, walking tracks, and more.
Hotel with Rooftop Pool Location: Lakeshore East Neighborhood a few blocks from Millenium Park and the Chicago River
How to Access the Rooftop Pool: Stay at the Hotel for the Pool Complex
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Holiday Inn Hotel & Suites Chicago – Downtown
The Hotel: The Holiday Inn Hotel + Suites Chicago Downtown is one of the cheaper and less luxurious options on this list that still has a great Chicago rooftop pool and is very centrally located. This hotel is only a few blocks away from the Sears/Willis Tower and also has a restaurant and a bar on-site.
The Rooms: The Rooms here are extremely basic, but what you would expect from a budget room. Many have pull-out sofa beds to squeeze more people in.
The Rooftop Pool: The rooftop pool may be the most basic, but it’s very spacious and quiet with plenty of deck chairs and not much else to bother you.
Hotel Location: Centrally Located in West Loop next to the Old Post Office and near Union Station, The University of Illinois Chicago, and Greek Town
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Kasa Chicago Old Town
The Hotel: Kasa Chicago Old Town is one of the lesser-known Chicago hotels with rooftop pools. It offers 22 apartments, a fitness center, and a rooftop terrace in the Old Town area of the Near North.
The Rooms: It’s more of an aparthotel as it has fully-equipped rooms ranging from studio to 1BR to 2BR, all with full kitchens, seating areas, general amenities, and often great views.
The Rooftop Pool: The rooftop pool at Kasa Hotel is one of the most spacious in the city. It offers a full 360-degree terrace with song of deck chairs and space to lay out and relax!
Hotel Location: Near North: between Gold Coast + Old Town – Near Chicago Station
How to Access the Rooftop Pool: You Must Be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Best Western River North Hotel
The Hotel: The Best Western River North is a great value hotel in Chicago’s downtown area a few blocks from the Magnificant Mile and Merchandise Mart. It’s got a pizzeria on-site as well as an indoor pool and outdoor area.
The Rooms: The rooms here are basic yet effective. They are simple with everything you need for a central hotel that also has a rooftop pool!
The Rooftop Pool: The rooftop pool is indoors, but there are plush lounge chairs and seating areas right outside for anyone who wants to relax in the sunlight with a view of the Chicago skyline.
Hotel Location: Off N LaSalle Dr. Chicago A few blocks from Grand Station
How to Access the Rooftop Pool: Must be a Hotel Guest
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Best Chicago Hotels with Rooftop Pools in West Loop/Fulton Market Area
Just outside of downtown, there are a few lovely Chicago hotels with rooftop pools in the West Loop area. This neighborhood is in an up-and-coming industrial-turned-trendy area also known as Fulton Market. It’s known for being artsy and a bit hipster- a great location to stay.
The Hoxton
The Hotel: The Hoxton Chicago is definitely one of the trendiest Chicago rooftop pool hotels on this list. A member of a bigger group of Hoxton Hotels, Chicago’s Hoxton location is awesome.
It’s located in an artsy district close to everything, but has so much on-site you won’t want to leave… including 3 bars/restaurants, a yoga studio, coffee shop, meeting space, and coworking space.
The Rooms: There are three super-cute room options: Roomy, Cosy, and Snug. This way you can choose how much space you need for your budget. However, all the rooms at ‘The Hox’ have great amenities, TV’s, views, and everything nice.
The Rooftop Pool: The Hoxton’s rooftop pool is surrounded by colorful furniture, day beds, tables and plants that create a wonderful fun vibe. The pool is part of a rooftop restaurant-bar called Cabra which specializes in Peruvian food and cocktails too.
Hotel Location: West Loop/Fulton Market Neighborhood Near Morgan Station
How to Access the Rooftop Pool: Stay at the Hotel for the Pool or Visit the Cabra Restaurant from 4pm Tues-Fri or 11am Sat-Sun.
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Soho House Chicago
The Hotel: This Chicago Hotel with rooftop pool isn’t as easy to get into as the others. The exclusive Soho House Chicago location is contained inside an old belt factory with industrial-chic decor, lounges, and furniture. There are three bars and a restaurant, including the epic rooftop bar.
The Rooms: If you’re lucky enough to get a membership, rooms here are as elegant as ever with trendy touches. There are a couple room styles – tiny, small, medium, medium plus, and big, all of which are equipped with vintage touches, branded toiletries and bedding, and Bluetooth speakers.
The Rooftop Pool: The Soho House Rooftop has a long and thin one-lane pool surrounded by plush deck chairs, lounges and tables. It also functions as an exclusive fairy-lit restaurant overlooking the city with top-notch food.
Hotel Location: West Loop/Fulton Market Neighborhood Near Morgan Station
How to Access the Rooftop Pool: You must be a member of Soho House to use the hotel OR rooftop pool!
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Hyatt House Chicago West Loop
The Hotel: The Hyatt House in West Loop is one of the more basic options in West Loop with a trendy bar and seating area inside the hotel as well as a fitness center.
The Rooms: The Hyatt House offers full kitchen suites and ‘dens’ in its West Loop property with luxurious amenities and well-equipped spaces.
The Rooftop Pool: There is an indoor rooftop pool at this Chicago hotel that offers panoramic views over the city. There’s also an outdoor fire pit, TV, and barbecue grill area that’s fantastic for relaxing or watching the sunset.
Hotel Location: West Loop/Fulton Market Neighborhood Near Morgan Station
How to Access the Rooftop Pool: For Hotel Guests
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
Best Chicago Hotels with Rooftop Pools Outside of Downtown
There are still more Chicago hotels with pools on rooftop that are outside of downtown. If you are looking for a hotel that’s a bit farther out in the suburbs or perhaps in a certain area, maybe one of these amazing selections will be for you!
The Robey
The Hotel: The Robey is an art deco design hotel located north of the city in the Wicker Park area of the city. This boutique hotel is in the historic Northwest Tower, the tallest building in the area which offers panoramic views of the city skyline. There are 3 different restaurants + bars onsite for all your needs.
The Rooms: The Robey offers a variety of minimalistic and boutique rooms styls that range from deluxe to ‘multiple bed’ lofts to suites. They’re all equipped with fantastic amenities.
The Rooftop Pool: The Robey hotel’s rooftop pool completes the vibe that is set out by its rooftop restaurant. The Cabana Club restaurant flanks the triangular rooftop pool on the 6th floor with panoramic city views. The Rooftop bar is up on the 13th (but no pool).
Hotel Location: Wicker Park Neighborhood – Near Damen Station
How to Access the Rooftop Pool: For Hotel Guests or Guests of the Cabana Club Restaurant open from 11am Daily
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –
The Hotel at Midtown
The Hotel: One of the most unique Chicage hotels with rooftop pools, The Hotel at Midtown is actually part boutique hotel and part Midtown Athletic Club. It’s also part soa, part restaurant, part bar, and more.
It’s designed for active travelers and includes access to one of Chicago’s best fitness centers including group fitness classes, yoga, indoor and outdoor pools, whirlpools, a boxing gym, and multiple bars and restaurants on site.
The Rooms: The rooms perfectly mirror the edgy and modern vibe of the whole hotel and fitness center. They are all cozy and colorful with luxurious amenities and spacious seating areas.
The Rooftop Pool: The Midtown has a huge lap pool on the roof, as well as an indoor lap pool also on the roof. There are outdoor fitness spaces as week as plenty of shairs to lay out under the shade and under the sun too.
Hotel Location: Bucktown Neighborhood Midtown Chicago – Near Riverpoint Center
How to Access the Rooftop Pool: For Hotel Guests or Athletic Club Members
– BOOK ON YOUR PREFERRED BOOKING PLATFORM –