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10 Best Airbnbs With A Pool In Chicago, Illinois - Updated 2020

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. Whether 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. Well, here is a list of the top Airbnb vacation rentals in Chicago, with a pool, compiled for you to choose from while in town. Read on to find out more!

1. Elegant family three-bedroom space (from USD 71)

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 museums.

BEautiful & Spacious Home for a Winter Getaway!
Chicago, Illinois, United States
81 reviews
Entire apartment 3 Beds 3 Bedrooms 1 Bathroom
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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2. Top-floor luxury apartment with great city views (from USD 98)

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
261 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
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3. Stunning restored luxury apartment near beach (from USD 59)

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.

Flat in Art Deco Private Club & Walk to Shows, Dining & L
Chicago, Illinois, United States
234 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
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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4. Splendid luxury apartment in Chicago Loop (from USD 205)

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
158 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
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5. 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 4 Guests

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6. 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

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7. 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

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8. 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

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9. Penthouse apartment

Embrace the homey feel offered by this two-bedroom apartment. 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
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10. 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
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Chicago's splendid apartment choices

The rentals are sure to satisfy your stay while in Chicago. They offer comfort without compromising on the luxury. Situated near the action area of Chicago’s top attractions, you will definitely have a fun stay in these Airbnb vacation rentals. Don’t wait, book now!

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