The city of Chicago is famous all over the world, and it’s not just because it is the third most populous city in the United States; it also stands out as a global leader and hub for finance, commerce, technology, telecommunications and transportation having some of the busiest airports in the world (O'Hare International Airport). Chicago is a world-class haven for the commercial, industrial and cultural sectors. The city on the shores of Lake Michigan is rich in top attractions in both the business world and the entertainment world. If it’s business or fun that brings you to Chicago, you may need a place to stay for the short duration of your travel or journey. Don’t know where to stay? Whether you’re looking for a luxury apartment or an Airbnb with a private pool in Chicago, we’ve got you covered! Check out these best Airbnbs with pool in Chicago, IL.
Located in the heart of Chicago is this exquisite restored one-bedroom apartment. It includes a well-furnished and fully fitted with contemporary style furniture, spotless bathroom and recreational areas where there is a state-of-the-art fitness center with a boxing gym, an alternative area with a large pool to cool off and relax and a fully equipped kitchen. Enjoy unwinding at the lounge with club seating, adjoining a cafe, a craft cocktail bar and a restaurant. The location is perfectly close to Chicago’s top attractions, including the beach.
Whole Flat in Private Club. Walk to L, Dining & ShowsChicago, Illinois, United StatesSuperhost
Top guest reviewsthe building comes with great amenities like a well-equipped gym and a swimming poolthe apartment was comfortable well-designed and felt like a home rather than a hotelthe apartment itself was fabulous with plenty of space and fun decornice room it's set up to work almost like a hotelsmall touches like chromecast qr codes so you can watch videos on the tv are really nicethe place was very clean and cozyaaron and carrie's space was clean and comfortable and their communication excellentthe apartment was perfectly clean and very well decoratedthe pool was nice and clean alittle cold thoughit was really clean comfortable and in a great location
Host:aaron was a great hosthe was fast at responding and helpful in answering our questionsaaron was a great host would definitely stay here againaaron was extremely helpful and responsive to all my requestsaaron was super responsive and helpfulRead more reviewsgreat location in chicago for a tripthis location had easy access to train and downtowngreat location and cool buildinggreat location for a visit to chicagostylish place in a great location
If you’re looking for a Chicago Airbnb with a pool, this one’s perfect for you. Suitable for up to five guests, this fully furnished apartment is very conveniently located in the Theater District of Chicago. Some of the city’s famous attractions like Navy Pier, Millennium Park, Riverwalk, and more are situated at a walking distance from the property.
Plus, guests will also have complete access to various building facilities, including a pool, a lounge, a hot tub, a fitness center, and a club room. The apartment has a furnished living area, a cozy bedroom, a spacious bathroom, a well-equipped kitchen, and a breakfast bar.
The Theater District HideawayChicago, Illinois, United States
Top guest reviewsthe amenities of the building were awesome we loved the hot-tub and pool the mostthe good: place was stylish and what you would expect from a modern apartmentthe apartment is clean and nicely furnishedit was clean spacious and comfortablehad netflix and was sparkling cleanthe place was sparkling clean stylish and comfortablethe shower was spacious clean and very nice with a rainfall style shower head
Host:stephanie was a very responsive hoststephanie is an excellent hoststephanie was a great host- quick responses and flexible with requestsstephanie was a great host who promptly asnwered all of our questionsstephanie was a great host with quick responses and helpful suggestionsRead more reviewsgood central location close to everythingthe location is in the perfect spot right downtown that’s close to everythingclose to great shopping and tourist sightsgreat location close to all we neededthe location was super convenient
Spacious and modern, this apartment in Chicago is very charming. It has a bright and open-concept living, dining and kitchen area that offers views of Lake Michigan. A stylish bathroom and a luxe bedroom complete the interior of this apartment. You will also have access to all the amazing amenities of the building like a gym, an indoor pool, and more. Grant Park is just a five-minute walk away from this Airbnb.
Sonder at Grant Park | Spacious One-Bedroom Apartment w/ Lake ViewChicago, Illinois, United States
Top guest reviewsamazing comfortable place - view is even better that in the photosbeautiful apartment with a great view that can’t be beatgreat view from the room as wellbeautiful views from both the bedroom and main space very modern and comfortablegreat stay and comfortable setting with a great view from the windowsthe room was really clean and stylishnice and clean place would definitely recommendvery clean and super quick and easy check in processvery clean & roomy for you to enjoy yourselfthe apartment was sparkling clean on arrival and had everything and more for our week long stay
Host:friendly staff and residentssonder staff was wonderful and extremely helpfulthank you sonder and staff for having us amazing staygreat location the staff were quick to respond to make sure my stay was enjoyablecheck-in was easy and very friendlyRead more reviewseasy & safe walk from the orange line station - roosevelt - direct from midway airportgreat location walk able to public transportation and restaurantsbeautiful apartment in a wonderful locationthe location is great with many restaurant optionsthe location was safe and perfect for getting around the city
A couple or two close friends traveling together to Chicago will find this Airbnb to be a very suitable accommodation option. On offer is a well-appointed room in a stylish apartment. Guests will also have access to common areas like a trendy dining room a workspace, a chic living room, a modern kitchen, and a full bathroom. The private room has a comfy bed, storage space, and a side table. Building amenities like a pool and a gym are also available for guest use. Located in a popular neighborhood, many breweries can be found in the area.
🏳️🌈Kick-Ass Stylish Flat with Kitties 🐱🏳️🌈 LGBTQ SAFEChicago, Illinois, United States
Top guest reviewseasily accessible and a comfortable spacecolin’s place is indeed a stylish place with a large modern kitchen and nicely decorated living roomthe apartment was so stylish and the cats were so sweet i definitely recommend this staythe place is very clean and updatedthe bed is comfy the house clean and the cats friendlythe unit was quiet clean well furnished and a great valuea wonderful place to stay in ravenswood very convenient clean and quietimpeccably clean and it seemed like we were alone all the time
Host:amazing host and lovely catshost is fast responder and uses easy virtual keycolin is a great host his hospitality and recomendations made all the difference for uscolin was a great hostlovely host and great room with everything you need including the smart tvRead more reviewscolin´s place is in a great part of town close to public transportwithin walking distance of the damen brown line station and some excellent restaurants10/10 would recommend nice place close to the train and easy neighborhood to walk around inthis a great location — close to lots of things and easy parkingbed was fairly comfortable the location was nice
Those looking for a private pool rental in Chicago will find this listing to be a very suitable option. Relaxing while in this spacious family-friendly or business travelers’ rental is just what the doctor ordered.
Located at the heart of the city of Chicago, this bright and welcoming home provides three bedrooms and a single bathroom and it comfortably accommodates six guests. Highlights include two decks, a patio heater, fire table, fire pit, grill, cooler and a pool for the guests to cool off during the hot summer. The location is great, being close to McCormick Place, the Midway Airport, Downtown, Lakefront, White Sox baseball Park, and various museums, which are some of the must-dos in The Windy City.
Pool Paradise Chicago Resort HomeChicago, Illinois, United StatesSuperhost
Top guest reviewsgreat backyard with deck swing pool and fire pitkitchen had all that we needed including an awesome coffee maker that ground beans (supplied)i had 3 boys with me so having the extra yard and pool were awesomethe house is so cozy and the yard is stunningthe space is gorgeous my friends and i (4 in total) were extremely comfortable hereit was clean cozy and smelled really goodbe’s space was very clean and invitingit was very nice clean and cozythe home was very clean and recently remodeledher house was very warming clean and welcoming everything we needed
Host:the host is amazingthe host was awesomebe was a wonderful hostbe was an amazing hostthe host is very nice and helpfulRead more reviewsthis location is super convenientgreat location quick commute to downtown and douglas parkthe location is in a safe residential chicago neighborhood so close to everythingvery cute and welcoming placewe enjoyed the location near a family member and fairly close to the city’s center museums etc
If you’re looking for an Airbnb with an indoor pool in Chicago, this property might interest you. Enjoy a gracious blend of Victorian style with a modern touch in this one-bedroom rental at the center of downtown, near Chicago. Three guests are able to enjoy the homey feel and the two beds available are large and comfortable. The decor is outstanding and you may not want to leave the premises after your duration of stay runs out. This top-floor apartment is situated in a high-rise area and offers a panoramic view of the city. It includes a full dining room and kitchen and the guests have access to the apartment building’s fitness center, yoga studio, indoor pool and sauna.
LUX 1BR/1BA Top-Floor Unobstructed Downtown ViewsChicago, Illinois, United States
Top guest reviewsbeautiful view and amazing apartmentvery comfortable bed & couch ( if you like softer beds)the views from the living room/bedroom are amazingthe view is stunning great location and the bed (and couch) are super comfortablethe apartment is nice and the view is goodthe apartment is very cleanwell appointed and very cleanthe apartmentwas very clean and felt like homewould absolutely stay here again cleanthe bed was very comfortable and everything was very neat and clean
Host:hosts had quick response time and were extremely helpful when neededhost was informative and easy to contactthey were very friendly responsive hosts and made sure all expectations were clear and questions were answeredmargarita and mike were super responsive before and during our stay when we had questionsmargarita was very accommodating and helpfulRead more reviewsgreat location for our trip to towngreat location and stylish spaceamazing place in amazing locationthe location was super convenientvery neat place with great location
This well-furnished studio rental is ideal for your business trips and holidays. You are provided with two large and comfortable beds for a maximum of four guests and the spectacular view of the city’s majestic skyline offered in and around the rental is one to behold. The elegant kitchen is complete with dishes and cutlery, electronic appliances like a microwave, fridge among others. After a long day’s work, you can take a swim in the building’s indoor pool. Also, you are provided with high-speed WiFi access as well as access to the building’s amenities.
Lovely Studio with Responsible Host (Super-view)
This stunning luxury apartment rental is located in the historic River North neighborhood in Chicago. The beautiful one-bedroom lofted ceiling rental is kept sparkling clean and features a queen bed, a pull-out couch, and an air mattress to accommodate a maximum of five guests within the unit. Other features in the apartment building include an indoor pool, a deck on the rooftop, a lounge as well as a business center among others. Incredible views of the city highlight the open space, great location and closeness to the nightlife, arts and entertainment in and around Chicago.
Downtown 1 Bedroom Luxury River North LoftChicago, Illinois, United States
You are guaranteed a fantastic stay in this elegant rental located near Lake Michigan. The spacious apartment has two large bedrooms with a total of six beds to accommodate a large traveling group or a family on vacation. The beds include three queen size regular beds, one queen sofa pull out bed and two futons. The two bathrooms are sparkling clean and the large windows allow for scenic viewing of the outside landscape as well as for entry of light into the home. Amenities in and around the apartment and the building include a flat-screen tv in each room a pool and a hot tub, TV, Starbucks Coffee, shopping centers within a five-minute walk, restaurant inside building and access to public transportation which is a five-minute walk from the rental.
5 bd 2 bth Swimming Pool View of lake by McCormickChicago, Illinois, United States
This elegant modern two-bedroom rental provides well-lit rooms and two sparkling clean bathrooms and accommodates up to six guests. Located in the River North area, the rental places you right in the middle of all Chicago ‘action’, as it’s only a walking distance to the city’s main attractions and entertainment. Enjoy the privacy and luxury experience offered by this rental that includes access to the apartment building’s amenities such as the gym, pool, sun deck, sauna, barbecue area, large social area. The cozy living room is spacious and well furnished. Private parking area in the compound can be arranged for the guest.
Luxurious Modern 2BR Center Downtown Chicago 502Chicago, Illinois, United States
Embrace the homey feel offered by this two-bedroom apartment with a pool in Chicago. Located right in the heart of Chicago’s Downtown Loop the well-furnished 38th-floor penthouse apartment provides a radiant interior and with the ideal balance of comfort and convenience, it is easy to tell why the guests cannot get enough of this luxury.
Accommodating up to five guests, the 360-degree private balcony will give you a breathtaking bird’s eye view of the city. Highlights of the apartment building include an indoor pool, hot tub, sauna, game area lounge, and business center among others.
AMAZING 38TH FLOOR PENTHOUSE IN LOOP HIGH RISE!Chicago, Illinois, United States
Top guest reviewsthe balcony surrounding the entire apartment is wonderfulfantastic historic building great penthouse views apartment and building amenities and downtown chicago locationamazing apartment with an amazing view on the sky linea place to stay to experience chicagopam at front desk is amazing fabulous workout room and balcony with the best view of the citythe apartment is cool and the space was perfect for usvery clean and well decoratedthe penthouse was fantastic and super cleanbeds were exceptionally comfortable the place clean if not a bit spartanvery much appreciated the space was clean and beautiful with great viewsplace was clean and everything on the add was there fully as expected
Host:jason was a great hostamazing host on top of all thatbuilding staff is super friendlythe host was great and a gentlemanjason is a super hostRead more reviewsthe condo is a great location to be in the heart of the citybeautiful place in a perfect locationalso it's super centralfantastic place in a superb location with beautiful architecturealways a great experience there great location with may things to do in walking distance
This one-bedroom delight situated next to the Millennium Park is a perfect choice for a solo traveler or a couple. Located at the center of Downtown, the spacious apartment offers a comfortable and clean rental for your short stay. You get a queen-sized bed for a great night’s sleep, one futon sofa, high-speed internet, a TV with complimentary Netflix, and complimentary breakfast food and drinks. Other highlights include heat and AC system as well as other building amenities like an indoor pool and a state-of-the-art fitness center.
Cozy 1br by Milllennium ParkChicago, Illinois, United States
Top guest reviewsthe wifi wasn’t the best so if traveling on business it’s good to knowloved the workout room upstairs the location and the viewsapartment is clean and spaciousthe rooms were clean & stocked with towelsgreat position clean and confortablethe apartment is extremely clean and they are very responsivethe place is really clean
Host:hosts are very quick with responses and helpfulhosts communicated well and were very responsive to my questionsgreat hosts that are responsive and welcomingthe host was very helpful with my checking inthe hosts are nice and very responsiveRead more reviewsclose to lots of great shopping and millennium parkthe location was very goodreally great location for visiting chicagogreat location great rental spacegreat location will stay again
A lavish artful two-bedroom apartment accommodating up to six guests is probably what you may be looking for. This modern contemporary apartment is a blend of unique style and luxury. Nestled in downtown Chicago, the rental features two sparkling bathrooms, two queen-sized beds with room darkening shades in the bedrooms, a modern kitchen with marble countertops, modern cookware, a refrigerator and stainless appliances. Guests have access to recreation areas including the fitness center, swimming pool and sauna as well as the outdoor common space if you fancy enjoying a relaxing outdoor experience.
Luxury Apartment 2BR 2BA Highrise/Millenimun ParkChicago, Illinois, United States
Top guest reviewscomfortable beds and furniturethe sofa opens into a sofa bed and comfortable as wellthe apartment is lovely and the views are out of this worldgreat apt with awesome view and very cleanit's a great apartment with a stunning view and a great location in chicagovery clean apartment & nicely decoratedsuper clean and exactly as describedit was also impeccably cleanthe apartment is incredibly clean and has multiple spacious roomscommunication was superb throughout our stay the unit was perfect clean and well stocked
Host:the host is so niceprince was a great hostprince was a great hostthe host is helpful available and quick with responsesthe host is very gracious and accommodatingRead more reviewsclose to all attractionslocation was fantasticgreat location right in the middle of everythingthe location is amazinggreat location train from airport stops inside building
Solo adventurers, business travelers or couples who are looking for comfortable accommodation in a central location in Chicago would love to stay at this Airbnb. Located on Magnificent Mile, this Airbnb is a private room in a furnished apartment. The room is clean, bright and appointed with a comfy bed. A spacious bathroom and a modern kitchen are also accessible to you. A gym, outdoor and indoor pools, fire pits, a sauna, basketball courts, and other amenities of the building will be available for guest use too. Due to its convenient downtown location, a range of trendy restaurants, bars and attractions are just a short walk away from this apartment.
Magnificent Mile!! Downtown Chicago views!!Chicago, Illinois, United States
Top guest reviewslovely place; incredible view very comfortablethe window of the room give a nice view on chicagothe room was nice and had an amazing view over the citythe view was absolutely amazing and the bed was comfortablegreat amenities at the apartment complex as wellthe place was clean and orderlythe place was very cleanhis place was clean and has a modern styleduring the stay it was clean & quiet oftenthe place was clean and fairly spacious especially the private bathroom
Host:charlie was a fantastic hostcharlie was nice hostcharlie was an absolutely awesome host and gave us great recommendationscharlie was very communicative and a great hostcharlie has an awesome place and is a great hostRead more reviewslocation was great within walking distance of most thingsthe location is unbeatable — being right in the middle of downtown close to every tourist attraction aroundthere is an amazing diner close by toovery nice place and great locationthe building is amazing in a perfect location
For a luxurious and chic stay in Chicago for six guests, choose this highrise condo. This elegantly furnished apartment has an open-concept living and dining area with floor-to-ceiling windows, a full kitchen, two luxurious bedrooms and bathrooms, and a balcony with lake views. Access to common building facilities like a rooftop pool, a sauna, a barbecue area, a gym, and more add to the appeal of this apartment. Magnificent Mile with its myriad eateries and attractions is just three blocks away.
Retro Style High Rise Condo with Lake View BalconyChicago, Illinois, United States
Top guest reviewsthe balcony has a great view & the kitchen had everything we needed to cookgreat apartment very nice style amazing view/balcony and location :)we loved the apartment and the deckbeautifully decorated & updated amenities in the apartmentwobbly coffee table) but it was much better than being stuck in a hotela modern & clean space in a well appointed buildingso clean and cozy amazing viewit is clean spacious with a good kitchen and facilitiesbright and clean amazing balconygreat location helpful to have a 24-hour doorperson clean and beautiful space
Host:great host will visit againhost was very nice and quick to respond to any questions i hadan incredibly stale experience unlike those that a true airbnb host can providelocation is fantastic and the place is beautiful the staff is also friendly and always willing to helpRead more reviewsgreat place and well locatedvery good location close to michigan ave and other attractionsbeautifully appointed apartment in a great locationbeautiful place in a good location we enjoyed our stayamazing location will want to stay here every time i’m in the windy city
Chicago's splendid apartment choices
The rentals are sure to satisfy your stay while in Chicago. Whether you’re looking for a sleek apartment or an Airbnb house with a pool in Chicago, these options offer comfort without compromising on luxury. Situated near the top attractions in Chicago, you will definitely have a fun stay in these Airbnb vacation rentals. Don’t wait, book now!
Frequently asked questions about the best Airbnbs with a pool in Chicago, Illinois
1. Which Airbnbs with a pool in Chicago offer a gym?
Several Airbnbs with a pool in Chicago offer access to a gym. For the best options, choose from the following Airbnbs: i) stunning restored luxury apartment near the beach ii) beautiful room for two in a stylish apartment iii) modern apartment with Lake Michigan views iv) private room in a Magnificent Mile apartment.
2. Which Airbnbs with a pool in Chicago have rooms with great views?
Many Airbnbs with a pool in Chicago have rooms with great views. For the best Airbnbs with views, take your pick from these options: i) top-floor luxury apartment with great city views ii) skyline view rental in Downtown iii) modern apartment with Lake Michigan views iv) chic high-rise condo with lake views.
3. Do any Airbnbs with a pool in Chicago offer breakfast?
Very few Airbnbs with a pool in Chicago offer breakfast. But if you’re keen on staying at a property that provides complimentary breakfast, then the best Airbnb for you would be this spacious one-bedroom in downtown.
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