Compare Vacation Rentals with Pools in Chicago

Located in Downtown Chicago's Magnificent Mile district, this penthouse offers stunning skyline views and is just a 5-minute walk to the Museum of Contemporary Art and a 15-minute walk to the Riverwalk.
This luxury apartment with a pool accommodates up to 8 guests with 3 bedrooms and features a private game room, a fully-equipped chef's kitchen, and access to building amenities including a heated lap pool and a rooftop sky club.

Enjoy a stay in Chicago's Loop district, just steps from Willis Tower and The Art Institute of Chicago, with Union Station a short train ride away.
This 650 sq ft apartment accommodates 2 guests and features a swimming pool, on-site BBQ area, game room, and in-unit laundry.

Centrally located in Chicago, this 1-bedroom apartment is just 500 feet from Millennium Park, The Bean, Navy Pier, the Riverwalk, and the museum campus, offering immediate walking access to iconic attractions.
Enjoy your stay in this luxurious apartment with a swimming pool, featuring a king bed, full bed, pull-out couch, and an air mattress for up to 5 guests, plus a private washer and dryer for ultimate convenience.

Enjoy a prime Loop location in Chicago, just steps from Michigan Avenue, theaters, shopping, and dining, with exceptional city views from this 1-bedroom apartment.
This apartment offers access to a swimming pool, fitness center, and other building amenities, perfect for a getaway with a pool in Chicago, accommodating up to 4 guests.

Enjoy exceptional city views from this luxurious 2-bedroom apartment located in Chicago's central cultural, historical, and business district, within walking distance of Millennium Park, Navy Pier, and the Riverwalk.
This apartment offers a fantastic getaway with an indoor swimming pool and access to a fitness center, sauna, and BBQ grills, perfect for unwinding after exploring Chicago.

Just 0.2 miles from the shores of Lake Michigan and Loyola Park, this studio apartment is located in a Chicago neighborhood with easy access to public transportation, grocery stores, and dining.
This apartment offers modern comfort with a queen-size bed, a fully equipped kitchen, and air conditioning, and is a great choice for travelers seeking a place with a pool.

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.

Enjoy a prime Downtown Chicago location, just 0.3 miles from Millennium Park and Lake Michigan, offering convenient access to State Street and Michigan Avenue shopping.
This family-friendly apartment, accommodating up to 5 guests, features a swimming pool, a fitness room, and a full kitchen with a dishwasher, fridge, and microwave.

Experience luxury in Chicago's Fulton Market district, just a 7-minute walk to Union Park and a 10-minute walk to Google HQ.
This 2-bedroom apartment offers 1350 square feet of space and access to building amenities including a swimming pool, ideal for your next pool getaway.

Located in Chicago's River North district, this resort offers convenient access to city landmarks.
Enjoy a luxurious one-bedroom suite with a private balcony, gourmet kitchen, and a state-of-the-art fitness center, all complemented by a seasonal outdoor heated pool and hot tub.

Located in Chicago's Loop district, this apartment offers excellent proximity to Willis Tower, The Art Institute of Chicago, and Millennium Park, with Union Station just a short train ride away.
This apartment features a private terrace and building amenities including a swimming pool, perfect for travelers seeking a getaway with a pool.

Centrally located on Michigan Avenue in Chicago, this apartment offers exceptional access to Millennium Park, The Bean, Navy Pier, and Soldier Field, with an 'L' train stop just 0.2 miles away for city-wide exploration.
This luxurious 2-bedroom apartment features a private washer and dryer, high-speed Wi-Fi, and a swimming pool, accommodating up to 5 guests with comfortable sleeping arrangements including a king bed, queen bed, and pull-out couch.

Located in Chicago's West Loop, this stylish studio is just a 5-10 minute walk from Union Station, placing you near Randolph Street's "Restaurant Row" and Fulton Market for dining and nightlife.
This studio accommodation offers a full kitchen, in-apartment laundry, and building amenities including a swimming pool, perfect for travelers seeking a getaway with a pool.

Experience top-floor lakefront privacy in Chicago's South Loop, offering sweeping city views just 2 minutes from Grant Park and 5 minutes from the Art Institute.
This family-friendly apartment, featuring 2 bedrooms and 2 bathrooms for up to 5 guests, boasts exclusive access to world-class amenities including indoor and outdoor swimming pools, a fitness center, and a 73rd-floor Sky Deck with an observation lounge, ensuring a memorable stay with a pool.

This Bensenville apartment is conveniently located minutes from downtown Elmhurst and the Rosemont Entertainment District, and only 21 miles from downtown Chicago.
Enjoy extensive entertainment options including unlimited free arcade games, massage chairs, slot machines, and a karaoke system, all complemented by an on-site indoor heated swimming pool, sauna, and steam shower.

Enjoy a downtown Chicago apartment with stunning river and skyline views, located just steps from the Chicago River and Lake Michigan, offering excellent access to city attractions and transit.
This family-friendly apartment, perfect for up to 3 guests, features a resort-style swimming pool, a full-size gym, and an in-unit washer & dryer, making it an ideal choice for travelers seeking a getaway with a pool.

Enjoy a studio resort in Chicago's West Loop, just a short walk from Union Station, offering convenient access to parks and grocery stores.
This resort features a swimming pool and is equipped with air conditioning, internet, and a fitness center, perfect for a comfortable stay with city views.

Located in Chicago's South Loop, this apartment offers convenient access to the city's attractions, just 0.5 miles from Grant Park.
This family-friendly apartment, perfect for up to 2 guests, features a swimming pool and a fitness center, providing a great getaway with a pool.

Located in Chicago's South Loop, this aparthotel is a 16-minute walk from Grant Park and one mile from the Art Institute of Chicago.
This 4-star aparthotel offers air-conditioned rooms with free Wi-Fi and city views, fully equipped kitchens, an outdoor fireplace area, and a swimming pool for guests to enjoy.

Enjoy an apartment in Chicago's entertainment district, just two blocks from the beach and one block from the Red Line 'L' train for easy access to Wrigley Field and the Loop.
This family-friendly apartment features a state-of-the-art fitness center, a 50-foot mosaic-tiled swimming pool, and a rooftop deck, offering a perfect urban getaway with a pool.

Enjoy a prime Theater District location in downtown Chicago, just steps from Millennium Park and State Street shopping, offering an exceptional base for exploring the city.
This modern, fully furnished studio apartment accommodates two guests and features a fully equipped kitchen, in-unit laundry, and access to a fantastic swimming pool and fitness center.

Enjoy a prime downtown Chicago location, just a 12-minute walk from the CIBC Theatre and 8 minutes from DePaul University, with Willis Tower only 0.9 miles away.
This spacious 5-bedroom apartment offers a private balcony with stunning lake views, ample room for 20 guests, and includes a fitness center and a swimming pool for your enjoyment.

Enjoy stunning lake views from this resort located between Lake Michigan and the Magnificent Mile.
This resort offers a swimming pool, Jacuzzi, and fitness center, perfect for a relaxing getaway.

Located in Chicago's River West neighborhood, this apartment offers quick access to Fulton Market, just 0.8 miles away, and Logan Square, 1.3 miles away.
This top-floor apartment sleeps 7 guests and features a fully-equipped kitchen, a Sonos sound system, Smart TVs, and access to a 24-hour gym, a yoga studio, and an outdoor swimming pool with a hot tub, making it an ideal choice for a getaway with a pool.

Enjoy stunning high-floor city views from this Near North Side apartment in Chicago's Miracle Mile, just 0.3 miles from Navy Pier and walking distance to the Museum of Contemporary Art and 360 Chicago.
This 710 sq ft, 1-bedroom apartment accommodates up to 2 guests and features a fully equipped kitchen, in-apartment laundry, and access to a swimming pool, perfect for a relaxing getaway.

Enjoy stunning city views from this downtown Chicago apartment in Greektown, just 0.5 miles from the Art Institute of Chicago and Michigan Avenue shopping.
This pet-friendly apartment offers a fully equipped kitchen, in-apartment laundry, and on-site amenities including a swimming pool, fitness center, and doorman, perfect for a getaway with a pool.

Enjoy a prime River North location in Chicago, just a 5-minute walk from Merchandise Mart and The Loop, offering city views and close proximity to Michigan Avenue shopping.
This modern one-bedroom apartment sleeps two and features a swimming pool, fitness center, and in-unit laundry, perfect for a getaway with a pool.

Enjoy panoramic city views from this high-floor studio apartment in Chicago's The Loop district, conveniently located near the railway.
This 580 sq ft apartment, accommodating 2 guests, features a swimming pool, fitness center, and in-apartment laundry, making it an ideal getaway with a pool.