Compare Vacation Rentals with Pools in Chicago

Enjoy an apartment in Chicago's Streeterville neighborhood, just a 5-minute walk from The Loop and close to Navy Pier and Michigan Avenue.
This 700 sq ft apartment offers a fully equipped kitchen, contemporary furnishings, and on-site amenities including a swimming pool, sauna, and doorman, perfect for guests seeking a getaway with a pool.

Offering panoramic city and sunset views from 50 stories high, this downtown Chicago apartment is located just 0.5 miles from the shores of Lake Michigan.
This luxury apartment features a private balcony, floor-to-ceiling windows, and resort-style amenities including a swimming pool and fitness center, perfect for up to 2 guests.

Located in Chicago's Loop, this studio is a 15-minute walk from Millennium Park and 0.9 miles from DePaul University.
This studio offers 620 square feet of space, accommodates up to 3 guests, and features a kitchen with a microwave and dishwasher, plus access to an indoor swimming pool and fitness center.

Explore this exceptional apartment in Chicago's Near North Side, just 0.2 miles from the renowned Miracle Mile and within walking distance of Navy Pier and the Museum of Contemporary Art.
This pet-friendly apartment offers modern furnishings, a fully equipped kitchen, in-apartment laundry, and building amenities including a swimming pool, perfect for a getaway with a pool.

Experience prime downtown Chicago living just 3 blocks from the Magnificent Mile, with iconic city views and an on-site market for essentials.
This aparthotel offers a spacious 2-bedroom apartment featuring a fully-equipped kitchen, laundry facilities, and a rooftop swimming pool with a sun deck, perfect for a memorable getaway with a pool.

Enjoy a Chicago getaway in the Near North Side, just a short walk from the Miracle Mile's shopping and dining, the Museum of Contemporary Art, and Navy Pier.
This one-bedroom apartment offers 680 square feet of living space and building amenities including a swimming pool, perfect for relaxation after exploring the city.

Enjoy a 4-bedroom apartment in Chicago's Magnificent Mile, just 500 feet from the Museum of Contemporary Art and a 10-minute walk to the Mag Mile itself.
This family-friendly apartment sleeps 14 and features a heated swimming pool, hot tub, fitness center, and a rooftop sky club, perfect for getaways with a pool.

Experience luxury urban living in a peaceful downtown Chicago neighborhood, just a short walk from grocery stores and top-rated restaurants.
This penthouse apartment offers stunning city and lake views, modern interiors, and access to a swimming pool, full-size gym, and 24/7 concierge service.

Located in Chicago's River North district, this apartment is just 500 feet from riverside parks and green spaces, offering quick access to Magnificent Mile shopping and the Loop business district.
This apartment features a swimming pool and offers 820 square feet of living space with two bedrooms and two bathrooms, ideal for up to six guests seeking a getaway with a pool.

Enjoy a sophisticated Chicago district stay with remarkable city views and convenient access to on-site amenities, including a seasonal outdoor heated swimming pool and hot tub.
This apartment offers a private balcony with stunning city vistas, in-suite laundry, a workspace, and access to a state-of-the-art fitness center, perfect for a relaxing getaway.

Enjoy a resort-style swimming pool in this premium two-bedroom apartment located in Chicago's Michigan Avenue area, just 0.3 miles from Grant Park and the Chicago Cultural Center.
This apartment accommodates up to 4 guests and features a fully equipped kitchen, in-unit laundry, and access to a fitness center and entertainment lounge.

This resort in Chicago's Fulton Market district offers direct access to the city's attractions and features a stunning seasonal outdoor heated swimming pool.
Enjoy a deluxe studio with a guest capacity of two, featuring a fully-equipped gourmet kitchen, private balcony with city views, and in-suite laundry, all complemented by a state-of-the-art fitness center and 24/7 concierge services.

Enjoy a luxurious Chicago apartment with a heated swimming pool, offering immediate access to premier dining and nightlife, just 500 feet from the Museum of Contemporary Art and a 10-minute walk to the Magnificent Mile.
This spacious 5-bedroom, 4-bathroom apartment accommodates up to 15 guests and features stunning city views, a chef's kitchen, a fitness center, and a 24/7 concierge for a high-quality stay.

This apartment in Chicago's West Loop offers immediate access to Union Park and Fulton Market, both within a 5-minute walk.
Enjoy a spacious 6-bedroom apartment with a swimming pool, accommodating up to 14 guests, featuring a chef's kitchen, private balconies, and building amenities like a fitness center and movie theater.

Located in Chicago's West Loop, this apartment is 1.1 miles from Union Station and 1.5 miles from Willis Tower.
Enjoy an outdoor swimming pool and a hot tub at this family-friendly apartment with a pool, offering stunning city views from private balconies and fully equipped kitchens.

Spectacular lake views and an indoor swimming pool highlight this family-friendly apartment located just over a mile from downtown Chicago, offering convenient access to the Field Museum, Grant Park, and DePaul University.
This apartment provides a private entrance, in-room hot tubs, a fitness center, and an on-site bar, ensuring a comfortable stay with a heated pool and free WiFi.

Spectacular cityscape and lake views are offered from this 38-story penthouse in Chicago's Gold Coast district, located steps from Michigan Avenue's renowned dining, shopping, and nightlife.
This spacious apartment, perfect for families, features a high-end chef's kitchen, mid-century modern furnishings, and full building amenities including a rooftop swimming pool, fitness center, and garage parking, accommodating up to 10 guests with a user rating of excellent.

Located in Chicago's Old Town district, this hotel is just a 14-minute walk to Oak Street Beach and close to Water Tower Chicago and 360 Chicago.
This hotel offers a spa, fitness center, and an outdoor swimming pool, perfect for a relaxing getaway.

Located in Chicago's River North district, this hotel is 1.5 miles from Oak Street Beach and near attractions like the Shops at Northbridge and Willis Tower.
Enjoy a refreshing dip in the hotel's seasonal outdoor swimming pool, perfect for a getaway with a pool, or relax in the sauna and hot tub.

Located in Chicago's Fulton Market district, this apartment is 7 minutes by car from Union Park and 10 minutes by car from Google HQ.
This apartment offers a unique blend of group connection and privacy with two same-floor units, sleeping up to 10 guests and featuring access to a 30,000 sq. ft. amenity space with a swimming pool, spa, and fitness center.

Located in Chicago's Central Station district, this apartment offers city views and is just 0.3 miles from Grant Park and Lake Michigan.
This 960 square feet apartment, accommodating up to 4 guests, features 2 bedrooms and 2 bathrooms and is equipped with a swimming pool, a sauna, and an indoor basketball court, perfect for a getaway with a pool.

Located in Chicago's River North district, this apartment is just minutes from The Magnificent Mile and across the river from the Loop business district, with riverside green spaces nearby.
This 750 square foot one-bedroom apartment accommodates up to 4 guests and features a swimming pool, a fully-equipped kitchen, and air conditioning, making it a perfect getaway with a pool.

Enjoy panoramic cityscape and lake views from this 38th-floor penthouse apartment located in Chicago's Gold Coast, just steps from Michigan Avenue and close to the Chicago History Museum and the Chicago Theatre.
This spacious 1500 sq ft apartment accommodates up to 10 guests and features a chef's kitchen with Gaggenau appliances, a rooftop swimming pool, and one complimentary parking space, offering a perfect urban getaway with a pool.

Located on North Elizabeth Street in Chicago, this apartment offers convenient access to the United Center, just an 18-minute walk away, and is situated 1.3 miles from Union Station and 1.7 miles from Willis Tower.
This spacious 1400 square foot, two-bedroom, two-bathroom apartment comfortably accommodates up to 11 guests and features a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, air conditioning, and an in-unit washing machine, perfect for travelers seeking a getaway with a pool.

Enjoy a prime Greektown location in this Chicago apartment, situated less than 0.6 miles from Union Station and a 14-minute walk from Willis Tower.
This 760 square foot apartment with a pool offers a fitness center, full kitchen, and year-round comfort with air conditioning, perfect for up to 3 guests seeking a getaway with a pool.

Enjoy city views from this 860 sq ft apartment located in Chicago's Loop, a 10-minute train ride from Union Station and within walking distance of Millennium Park and the Art Institute of Chicago.
This pet-friendly apartment offers a fully equipped kitchen, in-unit laundry, and access to building amenities including a swimming pool, making it a great choice for a getaway with a pool.

Located in Chicago's West Loop, this apartment is a 5-minute walk to Fulton Market and a 6-minute walk to Union Park, offering easy access to Little Italy and public transportation.
This spacious apartment accommodates up to 10 guests with 4 bedrooms and 4 bathrooms, and features a swimming pool along with a fitness center and rooftop terrace with grills and firepits.

Experience a luxury one-bedroom apartment in Downtown Chicago, just a 5-15 minute walk or drive from iconic spots like Navy Pier, Millennium Park, and the John Hancock Center, offering stunning city views.
This pet-friendly apartment provides exclusive access to a swimming pool, jacuzzi, 24/7 fitness center, and a clubhouse with workspaces, perfect for remote professionals and extended stays with high-speed Wi-Fi and an in-unit washer and dryer.