28 Best Airbnbs With Pool In Chicago, IL - Updated 2023

Daniel
Daniel  
Updated

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. Trendy apartment on the 14th floor (from USD 170)

This trendy apartment is located on the 14th floor, so you can expect to find stunning views of the city right out your window. Aside from that, this place is beautifully furnished. There’s a fully equipped kitchen, as well as a living room where you can relax. WiFi and television are provided, so you can stream all the movies and shows you want here.

You also have access to the on-site amenities. You can swim for an hour or two in the pool or lounge on the skyline deck during your downtime. You might also be interested in working out in the state-of-the-art fitness centre.

Modern 1 bedroom w/ luxury amenities in the Loop
Chicago, Illinois, United States
80 reviews  Wifi Available
Entire rental unit 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
very comfortable with awesome amenities and a great view
the amenities are fun -- check out the pool and ping pong
overall it was a great stay the most comfortable bed i’ve ever slept in in an air bnb
apartment is very cute has views & is supplied with everything you’ll need
the bed was super comfy
Cleanliness:
room was very clean and aesthetic
loved my stay super clean room and comfortable bed
things are clean and the apartment is spacious and the building friendly
wonderfully clean place with a great city view
clean for the most parts however the photos are not pictures of the actual apparent
Host:
staff members at the desk are friendly
the front desk is extremely helpful
the staff was super nice and helpful
everyone on staff was so friendly and helpful
building staff were extremely nice and very accommodating as well
Location:
amazing location everything we needed was within reasonable walking distance
great location walkable to so much plus close to the el
very easy walking distance to shops even with a stroller
fantastic location i loved being able to walk or catch the train so easily from this location
the place is located near a lot of tourists attractions
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2. Magnificent condo on the 51st floor (from USD 175)

Opulent living awaits you in this magnificent condo unit. Located on the 51st floor, this rental boasts breathtaking cityscape, and since there are many floor-to-ceiling windows here, you’ll always have a view wherever you are inside. You’ll also find many luxurious amenities inside. Premium appliances and utensils grace the kitchen, while high-quality linens are fitted on the two beds. All rooms also have their respective high-definition televisions.

The building also comes with many fantastic facilities. There’s a remodelled sundeck with a pool and a fire pit. If you love to work out, you’ll enjoy the fitness centre. For more fun, head out and explore the wonderful city of Chicago.

Best Location! LUX 2/2 Condo 51st fl Amazing Views
Chicago, Illinois, United States
4 reviews Superhost  Wifi Available
Entire condo 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Host:
chris was an amazing host and very accommodating to our needs
Location:
elegant modern convenient location
the location is perfect to be able to get around and do touristy things
Read more reviews

3. Cosy studio with fantastic amenities (from USD 77)

Even though this rental is only a cosy studio unit, it’s still wonderfully furnished. The bedroom features a plush-queen-size bed for two, while the kitchen has all the essential appliances and utensils you need to prepare scrumptious meals. For a relaxing and fun time, you can lounge in the living room, watching movies on the television.

For more fun, head out and enjoy the on-site amenities and facilities. Swim for an hour or two in the shared pool or work out at the gym. This rental is in the heart of Chicago, so you can also go on a sightseeing trip, visiting places such as Hyde Park, Lincoln Park, Near North Side, and Pilsen.

Steps to MI Ave Shops | View, Beach, Gym | Zencity
Chicago, Illinois, United States
29 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Location:
really good value for location would stay again
great location & space rooftop is definitely a plus
Read more reviews

4. Luxurious condo unit with beautiful city views (from USD 345)

Enjoy a luxurious vacation when you stay in this tastefully furnished condo unit. There are two beds — a king-size and a queen-size — and both feature pillow-top mattresses. The bedrooms also feature smart televisions. That way, you can watch movies from the comfort of your bed. This condo also boasts floor-to-ceiling windows, allowing lots of natural light in and giving you a glimpse of the city. Additionally, this rental comes with a full-size kitchen for your dining needs.

You’ll also have access to the other fantastic amenities available within the building. There’s a pool if you want to go for a refreshing swim, as well as a gym if you want to work out. You can also find more options for fun outside since this rental is located downtown. Check out the many shops, restaurants, and attractions in the area.

Lux Sky Home near Navy Pier and the Magnificent Mile
Chicago, Illinois, United States
30 reviews Superhost  Wifi Available
Entire condo 2 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
amazing views of the city great location close to everything and great amenities in the building (gym pool etc)
Cleanliness:
the apartment is gorgeous with great views clean and spotless and the hosts were extremely welcoming and responsive
Host:
everything was great the host was very responsive
the host was very communicative and made for a peaceful and enjoyable stay
the hosts are super responsive and interested in you having a great stay
honest and so easy to deal with rudy was so helpful and knowledgeable
he was extremely courteous and responsive
Location:
great location and a great space
the best location you can find in downtown chicago
the location couldn’t get any better just steps away from michigan ave
this unit was amazing the location was perfect
great place to stay for long term
Read more reviews

5. Newly updated rental unit in a prime location (from USD 155)

With three beds available, this newly updated rental unit can accommodate up to four people. If you’re travelling with a baby, a travel crib is available for you to use. You can also find a complete kitchen for your dining needs and a cosy living area with a television. WiFi access is available here as well.

You won’t get bored during your stay here because there are many things to do. You can take a refreshing dip in the on-site swimming pool. Or you can head to Lake Michigan or Ohio Street Beach since you have access to either attraction. Other places you might want to visit include the Navy Pier — and ride the Centennial Wheel while you’re at it — and the Chicago Riverwalk.

Magnificent views!
5 reviews  Wifi Available
Entire rental unit 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Cleanliness:
the place was very clean upon checking in
Host:
alex provided immediate responses to questions and was very helpful
alex was a great host and the unit is in a great location
Location:
it was my first time in chicago and the location is just perfect for everything
great location location location look out on the lake and navy pier every morning
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6. Contemporary studio unit near attractions (from USD 104)

This contemporary studio unit is located halfway between Old Town and River North, which means it’s in a great spot. Many iconic attractions are nearby, such as the Museum of Contemporary Art, the Wrigley Building, and 360 Chicago. Because of this, you shouldn’t miss the chance to go on a sightseeing tour and discover everything this city has to offer.

Once you’re done exploring Chicago, come back to this rental to relax. This cosy space has all the amenities you need for a comfortable stay. The queen-size bed is fitted with a memory-foam mattress, and the modern kitchen is complete. There’s also high-speed WiFi, so you can stream movies or work with ease.

You can also access on-site amenities, such as a seasonal pool, craft room, sundeck, and rooftop lounge.

Kasa | Everything You Need in Chicago | Old Town
Chicago, Illinois, United States
90 reviews  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the rooftop deck and pool were absolutely amazing so nice to be able to use those amenities
this apartment was compact but well designed with comfortable furnishings
beautiful apartment stocked with all the essentials
i had an incredibly comfortable stay and would come back
the unit was cute and cozy with a good feel and good view
Cleanliness:
building is clean and secure
it was clean and very nice
the building is clean modern and secure
it was a nice modern and clean studio
the apartment building/specific unit were unbelievably clean with nice modern finishes
Host:
great location clean apartment front desk staff was amazing i would stay here again
Location:
nice apartment in a great location
the gyms are great and the location is awesome if you want to stay close to downtown
walking distance to the train and all of the attractions
pretty much everything is within walking distance
we were also close enough to walk to multiple places which was great to not deal with parking
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7. Bright and airy apartment perfect for small groups (from USD 206)

This apartment has only one bedroom with a king-size bed, but there is an extra sofa bed in the living room. For that reason, up to four people can stay here, making this rental perfect for small groups. Additionally, this apartment features a fully equipped gourmet kitchen, in-suite laundry facilities, and a living room with a flat-screen television. High-speed WiFi is also provided here.

To make the most of your vacation, be sure to take advantage of the on-site amenities. If you love to swim, there’s an outdoor heated pool that you can use. You’re also free to soak in the hot tub if you feel tired and sore. Other amenities you can enjoy include the state-of-the-art fitness centre, outdoor basketball and bocce ball court, and secured self-parking.

Level ◆ One Bedroom Deluxe + Balcony | Old Town
Chicago, Illinois, United States
10 reviews Superhost  Wifi Available
Entire serviced apartment 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
we had an amazing stay the room was very clean and the building amenities were convenient and well kept
Cleanliness:
clean and lots of nice amenities
great place very clean fantastic amenities perfect location
Location:
spot hero parking garages located close by
the location is awesome with tons of restaurants cafes grocery stores the (website hidden by airbnb) was great
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8. Completely refurbished suite with free parking (from USD 195)

This completely refurbished suite features a private bedroom with two queen size beds and a TV and can accommodate up to four people. It also has a well-kept bathroom, a fully equipped kitchen, and a dining area. You will also have access to a shared pool, into which you can plunge yourself, as well as a deck, upon which you can recline and unwind.

If you want to make the most of your stay, there is a beautiful garden that you can explore, as well as a grill where you can have a night of grilling some meat. For your comfort and convenience, amenities such as WiFi, a heating and cooling system, bathroom and laundry essentials, and free street parking are available.

Sweet Home Chicago-walk to White Sox, free parking
Chicago, Illinois, United States
43 reviews Superhost  Wifi Available
Entire guest suite 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
nice patio grill and pool in the backyard is definitely a plus
she's a very great host and offers fresh coffee and cereal for breakfast
they've done a terrific job renovating this garden apartment
her place is so comfortable and there is plenty of space
Cleanliness:
the house is clean and comfortable
the room were impeccably clean and it really felt
rooms are clean and beds are comfortable
well decorated and clean with a nice kitchen area
excellent place to spend time clean and spacious
Host:
she was a great host
excellent host and great response time
the hosts were quick to communicate and so kind
and the host is very responsive :)
great host and great place to stay
Location:
great location close to downtown chicago
close to local attractions
easy commute to downtown by train/bus/ bike and plenty of parking if you're driving
great location and very spacious home
the house was great and it was close to a lot of restaurants
Read more reviews

9. Modern rental with floor-to-ceiling windows (from USD 125)

Boasting floor-to-ceiling windows, this modern rental unit gives you a stunning glimpse of Chicago, including Lake Michigan. Aside from the beautiful views, you’ll also find that this unit is tastefully furnished. The kitchen is fully equipped, allowing you to cook gourmet meals with ease. Meanwhile, the living room has a television, so you can watch movies whenever you want.

For more fun, feel free to use the available facilities in the building. You can enjoy a refreshing swim in the seasonal pool, or you might be interested in exercising in the 24-hour gym. If you’re bringing a car to Chicago, there’s free parking on the premises.

Modern Floor to Ceiling Loft - City/Lake Views
81 reviews Superhost  Wifi Available
Entire rental unit 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Host:
amy was also an amazing host definitely looking forward to visiting chicago again soon
the sweetest energy hospitable and rare to come across such a great host
couldn’t recommend the place more amy is a wonderful host and the stay was smooth and without issue
Location:
victory tap across the street had great italian food
it was in a great area only a mile away from grant park millennium park etc
if you feel like cooking go grocer is conveniently located across the street
also was an easy and safe walk to convention center
would highly recommend if looking for location view and overall value
Read more reviews

10. Well-equipped condo with skyline views (from USD 100)

The wonderful views of the Chicago skyline await you in this two-bedroom flat. Convenient and centrally located, this home offers a soothing environment that’s sure to help you relax throughout your stay. The kitchen comes with a refrigerator, stove, dishwasher, and microwave for your cooking needs. There is also a printer and dedicated workspace for your convenience.

Complementing these amenities are the building’s large outdoor pool, barbecue area with tables and chairs, wonderful roof deck, gym, and movie theatre viewing room. This flat is only a ten-minute walk from Oak Street Beach, two blocks from Michigan Avenue, and is close to Magnificent Mile.

River North 2 bedroom condo with fabulous views
Chicago, Illinois, United States
20 reviews Superhost  Wifi Available
Entire condo 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
it would be perfect if the pool wasn't under construction
Cleanliness:
excellent location and fun neighborhood very clean very comfortable king bed comfortable soaking tub comfortable furniture
Host:
the host was super quick in responding definitely would recommend this place for anyone wants to stay in chicago
lynne is an all star host with an equally great airbnb
Location:
a superb location in downtown chicago
great apartment and great location
everything about the place was as advertised the location was great near everything that i needed (subway/beach/restaurant/shopping mall)
i highly recommend lynn's place whoever needs to stay near magnificent mile
location was the best it could be had a wonderful stay and lynne was responsive and helpful
Read more reviews

11. Lakeview penthouse with pool and hot tub access (from USD 345)

This posh penthouse offers panoramic views of Lake Michigan and Chicago’s skyline through its large balcony and huge picture windows in all three bedrooms and the living area. A flat-screen TV, WiFi, a modern kitchen, and other top-notch amenities provide comfort and convenience. The outdoor pool, hot tub, yoga studio, business center, and other great amenities can also be accessed by guests.

The building is located within the renowned Loop area. It’s where you can find so many attractions like the iconic Cloud Gate sculpture and Millennium Park. You can also enjoy numerous eclectic shops, hip bars, top-notch restaurants, and a lot more in this trendy area.

XL Pent House for 6 "The Harper" Full Amenities
Chicago, Illinois, United States
67 reviews Superhost  Wifi Available
Entire rental unit 5 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
very comfortable and nice furniture and fixtures
the beds are so comfortable and the view is the most amazing view i’ve even seen in chicago
view from apartment is amazing
stunning views hip location super clean and comfortable space plethora of nice building amenities
you do not need reservations to use the pool and it was great lots of lounge chairs
Cleanliness:
great penthouse very clean and equipments are fully prepared
the unit is beautiful and clean with wonderful views
extremely clean giving the feeling of home away from home
Host:
the host was really communicative and welcoming
the host was very responsive with communications
that along with wonderful and attentive hosts made this just a delightful stay
exceptional host highly recommend cloud9
easy checkin and very accommodating with swift communication
Location:
amazing location and flawless experience
amazing property perfect location
great space in a fantastic location
loved how close it was to all the michelin star restaurants
great location and space for our girls trip
Read more reviews

12. High-end staycation spot in the heart of Gold Coast (from USD 175)

Located in Gold Coast, the most sought-after neighborhood in the city, this staycation spot is all about comfort and luxury. This apartment features a stylish open floor plan with a king bed, a sofa bed, and an air mattress to sleep up to four in total comfort. The kitchen is furnished with a fridge, microwave, coffeemaker, and more for easy food preparation. Guests will also have access to great building facilities including a pool, a gym, and a furnished patio on the roof deck.

You can find some of the best restaurants in Windy City nearby. You can also easily get to other parts of the city via public transportation, which is located close to the building.

🌆☀️Gold Coast Lavish Home w/ Roof Pool & Gym ☀️🌆
Chicago, Illinois, United States
50 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
nice view from large living room and bedroom windows
wifi and tv was good and we loved nba jams
the roof top is amazing but be prepared for lots of parties and an unheated pool
great host and very communicative rooftop pool and deck is spectacular
Cleanliness:
very clean place to stay
place was clean and beautiful just as advertised
other than that it was clean and easy check in
very neat and clean
the location is perfect the apartment is very clean and the rooftop/gym/pool area is amazing
Host:
patricia was a great host and very responsive
and the host who wasn’t even apologetic nothing more than a “i didn’t know please find a hotel”
Location:
great location walking distance to the magnificent mile
location is everything and this place is perfectly located
really fun and central place
beautiful place and great location in the heart chicago
this place was in a great location 2 blocks from michigan ave
Read more reviews

13. Modern penthouse with city views (from USD 345)

Whether you’re here for business or leisure, your trip to Chicago will be a lot more delightful by booking a stay in this luxurious penthouse apartment. The first thing you’ll probably notice in this accommodation is its floor-to-ceiling windows that not only allow plenty of natural light in but provide you with a spectacular view of the cityscape.

The modern interior design exudes elegance that’s paired with the conveniences of modern amenities—from the fully equipped kitchen to the flat-screen TV. Guests can also enjoy the building facilities including an outdoor pool, a yoga studio, and a business center.

XL Pent House for 6 "The Harper" Full Amenities
Chicago, Illinois, United States
67 reviews Superhost  Wifi Available
Entire rental unit 5 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
very comfortable and nice furniture and fixtures
the beds are so comfortable and the view is the most amazing view i’ve even seen in chicago
view from apartment is amazing
stunning views hip location super clean and comfortable space plethora of nice building amenities
you do not need reservations to use the pool and it was great lots of lounge chairs
Cleanliness:
great penthouse very clean and equipments are fully prepared
the unit is beautiful and clean with wonderful views
extremely clean giving the feeling of home away from home
Host:
the host was really communicative and welcoming
the host was very responsive with communications
that along with wonderful and attentive hosts made this just a delightful stay
exceptional host highly recommend cloud9
easy checkin and very accommodating with swift communication
Location:
amazing location and flawless experience
amazing property perfect location
great space in a fantastic location
loved how close it was to all the michelin star restaurants
great location and space for our girls trip
Read more reviews

14. Stunning restored luxury apartment near beach (from USD 94)

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
388 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
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

15. Stylish rental best for couples (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
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

16. Lovely resort home best for families (from USD 134)

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.

Spacious Holiday Getaway for Family & Friends
Chicago, Illinois, United States
118 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
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

17. Downtown apartment with city views

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

18. 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

19. Lakeview rental with access to pool and hot tub

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

20. 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

21. Penthouse apartment with hot tub access

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
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
Cleanliness:
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
Host:
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
Location:
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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22. Cozy unit best for couples or solo travelers

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
Cleanliness:
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
Host:
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
Location:
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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23. 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
Cleanliness:
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
Host:
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
Location:
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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24. 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
Cleanliness:
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
Host:
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:
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
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25. Elegant 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
Cleanliness:
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
Host:
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
Location:
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
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26. Charming apartment with Lake Michigan views

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
225 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
Cleanliness:
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
Host:
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
Location:
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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27. Beautiful hideaway with access to hot tub

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
179 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
Cleanliness:
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
Host:
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
Location:
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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28. Well-furnished apartment with hot tub access

Enjoy all that Chicago has to offer in this luxurious two-bedroom apartment for up to six. Located in the middle of cultural, historical, and business attractions, this apartment guarantees convenience in touring the city. It’s only a walking distance from Millennium Park, the famous Bean (Cloud Gate), Navy Pier, and Chicago Riverwalk.

The apartment itself boasts incredible views of the city as well as amenities like a king-sized bed, pull-out couch, and Roku. The building also features a hot tub, swimming pool, lounge, and business center for your further relaxation.

The Professional’s Playground (2BR)
Chicago, Illinois, United States
253 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the tv and couch is great
apartment overlooks the train tracks and i enjoyed hearing the train occasionally roll through
i recommend this apartment for couples and families visiting chicago
Cleanliness:
very clean nice and quiet
really clean place and great kitchen
clean cozy and super comfortable
very spacious apartment with a sparkling clean interior
nice clean and a peaceful ambiance
Host:
host was very responsive
stephanie was amazing along with the staff here
make sure host knows to communicate with the people up front
stephanie communicated with us very well and is a super awesome host
host was very responsive to work out issues
Location:
the riverwalk and many attractions are close by and within walking distance
great location we liked the building and the great location
amazing location to experience downtown chicago
what an amazing location right in the loop walking distance to nearly everything
besides that great location
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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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