15 Best Airbnbs With Pool In Chicago, IL - Updated 2021

airbnb chicago pool

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.

1. Stunning restored luxury apartment near beach (from USD 122)

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 & Shows
Chicago, Illinois, United States
302 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the building comes with great amenities like a well-equipped gym and a swimming pool
the apartment was comfortable well-designed and felt like a home rather than a hotel
the apartment itself was fabulous with plenty of space and fun decor
nice room it's set up to work almost like a hotel
small touches like chromecast qr codes so you can watch videos on the tv are really nice
the place was very clean and cozy
aaron and carrie's space was clean and comfortable and their communication excellent
the apartment was perfectly clean and very well decorated
the pool was nice and clean alittle cold though
it was really clean comfortable and in a great location
aaron was a great host
he was fast at responding and helpful in answering our questions
aaron was a great host would definitely stay here again
aaron was extremely helpful and responsive to all my requests
aaron was super responsive and helpful
great location in chicago for a trip
this location had easy access to train and downtown
great location and cool building
great location for a visit to chicago
stylish place in a great location
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2. Furnished apartment in Theater District (from USD 143)

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 Hideaway
Chicago, Illinois, United States
143 reviews  Wifi Available
Entire rental unit 2 Beds 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the amenities of the building were awesome we loved the hot-tub and pool the most
the good: place was stylish and what you would expect from a modern apartment
the apartment is clean and nicely furnished
it was clean spacious and comfortable
had netflix and was sparkling clean
the place was sparkling clean stylish and comfortable
the shower was spacious clean and very nice with a rainfall style shower head
stephanie was a very responsive host
stephanie is an excellent host
stephanie was a great host- quick responses and flexible with requests
stephanie was a great host who promptly asnwered all of our questions
stephanie was a great host with quick responses and helpful suggestions
good central location close to everything
the location is in the perfect spot right downtown that’s close to everything
close to great shopping and tourist sights
great location close to all we needed
the location was super convenient
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3. Modern apartment with Lake Michigan views (from USD 589)

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 View
Chicago, Illinois, United States
187 reviews  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
amazing comfortable place - view is even better that in the photos
beautiful apartment with a great view that can’t be beat
great view from the room as well
beautiful views from both the bedroom and main space very modern and comfortable
great stay and comfortable setting with a great view from the windows
the room was really clean and stylish
nice and clean place would definitely recommend
very clean and super quick and easy check in process
very clean & roomy for you to enjoy yourself
the apartment was sparkling clean on arrival and had everything and more for our week long stay
friendly staff and residents
sonder staff was wonderful and extremely helpful
thank you sonder and staff for having us amazing stay
great location the staff were quick to respond to make sure my stay was enjoyable
check-in was easy and very friendly
easy & safe walk from the orange line station - roosevelt - direct from midway airport
great location walk able to public transportation and restaurants
beautiful apartment in a wonderful location
the location is great with many restaurant options
the location was safe and perfect for getting around the city
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4. Beautiful room for two in a stylish apartment (from USD 38)

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 SAFE
Chicago, Illinois, United States
74 reviews  Wifi Available
Private room in rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
easily accessible and a comfortable space
colin’s place is indeed a stylish place with a large modern kitchen and nicely decorated living room
the apartment was so stylish and the cats were so sweet i definitely recommend this stay
the place is very clean and updated
the bed is comfy the house clean and the cats friendly
the unit was quiet clean well furnished and a great value
a wonderful place to stay in ravenswood very convenient clean and quiet
impeccably clean and it seemed like we were alone all the time
amazing host and lovely cats
host is fast responder and uses easy virtual key
colin is a great host his hospitality and recomendations made all the difference for us
colin was a great host
lovely host and great room with everything you need including the smart tv
colin´s place is in a great part of town close to public transport
within walking distance of the damen brown line station and some excellent restaurants
10/10 would recommend nice place close to the train and easy neighborhood to walk around in
this a great location — close to lots of things and easy parking
bed was fairly comfortable the location was nice
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5. Elegant family three-bedroom space (from USD 198)

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 Home
Chicago, Illinois, United States
102 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
great backyard with deck swing pool and fire pit
kitchen 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 awesome
the house is so cozy and the yard is stunning
the space is gorgeous my friends and i (4 in total) were extremely comfortable here
it was clean cozy and smelled really good
be’s space was very clean and inviting
it was very nice clean and cozy
the home was very clean and recently remodeled
her house was very warming clean and welcoming everything we needed
the host is amazing
the host was awesome
be was a wonderful host
be was an amazing host
the host is very nice and helpful
this location is super convenient
great location quick commute to downtown and douglas park
the location is in a safe residential chicago neighborhood so close to everything
very cute and welcoming place
we enjoyed the location near a family member and fairly close to the city’s center museums etc
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6. Top-floor luxury apartment with great city views

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 Views
Chicago, Illinois, United States
285 reviews
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
beautiful view and amazing apartment
very comfortable bed & couch ( if you like softer beds)
the views from the living room/bedroom are amazing
the view is stunning great location and the bed (and couch) are super comfortable
the apartment is nice and the view is good
the apartment is very clean
well appointed and very clean
the apartmentwas very clean and felt like home
would absolutely stay here again clean
the bed was very comfortable and everything was very neat and clean
hosts had quick response time and were extremely helpful when needed
host was informative and easy to contact
they were very friendly responsive hosts and made sure all expectations were clear and questions were answered
margarita and mike were super responsive before and during our stay when we had questions
margarita was very accommodating and helpful
great location for our trip to town
great location and stylish space
amazing place in amazing location
the location was super convenient
very neat place with great location
Read more reviews

7. Skyline view rental in Downtown

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)
59 reviews
Entire apartment 2 Beds

8. Luxury downtown one-bedroom apartment

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 Loft
Chicago, Illinois, United States
125 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

9. Spectacular two-bedroom rental with lakeview

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 McCormick
Chicago, Illinois, United States
97 reviews
Entire apartment 6 Beds 2 Bedrooms 2 Bathrooms

10. Luxury two-bedroom in central Chicago

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 502
Chicago, Illinois, United States
219 reviews
Entire apartment 2 Beds 2 Bedrooms 2 Bathrooms

11. Penthouse apartment

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.

Chicago, Illinois, United States
91 reviews
Entire apartment 2 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the balcony surrounding the entire apartment is wonderful
fantastic historic building great penthouse views apartment and building amenities and downtown chicago location
amazing apartment with an amazing view on the sky linea place to stay to experience chicago
pam at front desk is amazing fabulous workout room and balcony with the best view of the city
the apartment is cool and the space was perfect for us
very clean and well decorated
the penthouse was fantastic and super clean
beds were exceptionally comfortable the place clean if not a bit spartan
very much appreciated the space was clean and beautiful with great views
place was clean and everything on the add was there fully as expected
jason was a great host
amazing host on top of all that
building staff is super friendly
the host was great and a gentleman
jason is a super host
the condo is a great location to be in the heart of the city
beautiful place in a perfect location
also it's super central
fantastic place in a superb location with beautiful architecture
always a great experience there great location with may things to do in walking distance
Read more reviews

12. Spacious one-bedroom in Downtown

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 Park
Chicago, Illinois, United States
352 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the wifi wasn’t the best so if traveling on business it’s good to know
loved the workout room upstairs the location and the views
apartment is clean and spacious
the rooms were clean & stocked with towels
great position clean and confortable
the apartment is extremely clean and they are very responsive
the place is really clean
hosts are very quick with responses and helpful
hosts communicated well and were very responsive to my questions
great hosts that are responsive and welcoming
the host was very helpful with my checking in
the hosts are nice and very responsive
close to lots of great shopping and millennium park
the location was very good
really great location for visiting chicago
great location great rental space
great location will stay again
Read more reviews

13. Splendid luxury apartment in Chicago Loop

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 Park
Chicago, Illinois, United States
178 reviews
Entire apartment 3 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
comfortable beds and furniture
the sofa opens into a sofa bed and comfortable as well
the apartment is lovely and the views are out of this world
great apt with awesome view and very clean
it's a great apartment with a stunning view and a great location in chicago
very clean apartment & nicely decorated
super clean and exactly as described
it was also impeccably clean
the apartment is incredibly clean and has multiple spacious rooms
communication was superb throughout our stay the unit was perfect clean and well stocked
the host is so nice
prince was a great host
prince was a great host
the host is helpful available and quick with responses
the host is very gracious and accommodating
close to all attractions
location was fantastic
great location right in the middle of everything
the location is amazing
great location train from airport stops inside building
Read more reviews

14. Private room in a Magnificent Mile apartment

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
40 reviews
Private room in apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
lovely place; incredible view very comfortable
the window of the room give a nice view on chicago
the room was nice and had an amazing view over the city
the view was absolutely amazing and the bed was comfortable
great amenities at the apartment complex as well
the place was clean and orderly
the place was very clean
his place was clean and has a modern style
during the stay it was clean & quiet often
the place was clean and fairly spacious especially the private bathroom
charlie was a fantastic host
charlie was nice host
charlie was an absolutely awesome host and gave us great recommendations
charlie was very communicative and a great host
charlie has an awesome place and is a great host
location was great within walking distance of most things
the location is unbeatable — being right in the middle of downtown close to every tourist attraction around
there is an amazing diner close by too
very nice place and great location
the building is amazing in a perfect location
Read more reviews

15. Chic high-rise condo with lake views

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 Balcony
Chicago, Illinois, United States
53 reviews
Entire condominium 2 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the balcony has a great view & the kitchen had everything we needed to cook
great apartment very nice style amazing view/balcony and location :)
we loved the apartment and the deck
beautifully decorated & updated amenities in the apartment
wobbly coffee table) but it was much better than being stuck in a hotel
a modern & clean space in a well appointed building
so clean and cozy amazing view
it is clean spacious with a good kitchen and facilities
bright and clean amazing balcony
great location helpful to have a 24-hour doorperson clean and beautiful space
great host will visit again
host was very nice and quick to respond to any questions i had
an incredibly stale experience unlike those that a true airbnb host can provide
location is fantastic and the place is beautiful the staff is also friendly and always willing to help
great place and well located
very good location close to michigan ave and other attractions
beautifully appointed apartment in a great location
beautiful place in a good location we enjoyed our stay
amazing location will want to stay here every time i’m in the windy city
Read more reviews

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I am a sports enthusiast and enjoy football. I love visiting new places and listening to music, as well as reading novels. That's my quick bio.

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