Compare Vacation Rentals with Pools in Chicago

Enjoy a prime South Loop location, just a short walk from Grant Park and Millennium Park, offering an excellent base for exploring Chicago.
This spacious 4-bedroom apartment, accommodating up to 10 guests, features floor-to-ceiling windows, a full kitchen, in-unit laundry, and a rooftop swimming pool with city views, perfect for a getaway with a pool.

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.

Enjoy stunning city views from this one-bedroom apartment located in Chicago's Greektown, offering convenient access to local attractions and a prime location.
This apartment includes a swimming pool, a fitness center, and is pet-friendly, perfect for travelers seeking a getaway with a pool.

Enjoy breathtaking city views from this 9-bedroom, 8-bathroom apartment in Chicago's River West neighborhood, just a 5-minute walk to Logan Square and a 7-minute walk to Fulton Market.
This spacious apartment offers luxurious living with a swimming pool, a 24-hour gym, a yoga studio, and a hot tub, accommodating up to 21 guests with high-end in-unit features like Sonos sound systems and Smart TVs.

Enjoy exceptional city views from this luxurious 2-bedroom apartment, perfectly situated in a central Chicago district, just a few blocks from an 'L' train stop for easy city exploration and within walking distance to Millennium Park, Navy Pier, and The Field Museum.
This apartment offers a premium experience with access to an outdoor swimming pool, fitness center, sauna, and other building amenities, ideal for travelers seeking a relaxing getaway with a pool.

Enjoy a downtown Chicago apartment with a pool, located less than 0.6 miles from the Art Institute of Chicago and a 7-minute walk from Grant Park.
This 1160 square foot apartment features four bedrooms, three bathrooms, and accommodates up to 15 guests, offering on-site amenities including a swimming pool, sauna, and fitness center.

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.

Located in Chicago's River West district, this premium 1BR apartment offers an immersive urban experience.
This apartment features a swimming pool, fitness center, and parking, perfect for city explorers seeking comfort with a pool.

This Chicago apartment is located in the West Loop, a 5-10 minute walk from Union Station and close to "Restaurant Row" and Fulton Market.
Enjoy a comfortable stay in this apartment with a swimming pool, offering stunning city views, a fully equipped kitchen, in-apartment laundry, and a fitness center.

Enjoy a modern one-bedroom apartment in Chicago's West Loop, offering immediate comfort and an ideal proximity to prime attractions, all with a fantastic swimming pool.
This stylish apartment features a fully equipped kitchen, air conditioning, and a fitness center, providing a complete stay with a swimming pool for relaxation and recreation.

Enjoy a luxurious apartment stay in Chicago, conveniently located in a residential area just 15 minutes from Downtown and O'Hare Airport, and 20 minutes from Wrigleyville and Lincoln Park.
This spacious 2700 square foot apartment accommodates up to 14 guests with 4 bathrooms and features a private outdoor patio, gazebo, and a celebrated 5-star outdoor kitchen with a gas BBQ grill, alongside a swimming pool for an unforgettable getaway.

Located in Chicago's Loop, this apartment offers premier access, just 10 minutes by foot from Skydeck Chicago and 0.25 miles from Millennium Park.
This spacious apartment sleeps 20 and features a fully-equipped kitchen, Smart TVs, and access to an outdoor swimming pool, sundeck, and fitness center, perfect for a large group getaway with a pool.

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.

This luxury apartment is located in Chicago's Loop district, within half a mile of downtown Chicago and close to attractions like the CIBC Theatre and Willis Tower.
Enjoy a refreshing escape with city views from the rooftop swimming pool, and take advantage of the complimentary WiFi, air-conditioned units, and on-site garden in this family-friendly apartment.

Enjoy an excellent user and location rating at this 2400 sq ft, 3-bedroom, 2-bathroom Chicago apartment located in the Hermosa neighborhood, offering convenient access to public transportation and downtown attractions, just miles from Logan Square, Wicker Park, and Lakeview.
This family-friendly apartment comes with a swimming pool, a private garage with a party door and tiki bar, a deck with a fire pit, and is professionally cleaned and sanitized before each reservation for your peace of mind.

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.

Located in Streeterville, this apartment is a 5-minute walk from The Loop and close to Lake Michigan.
This one-bedroom apartment offers 640 square feet of living space, a modern kitchen, in-unit laundry, and access to a swimming pool, making it an ideal getaway with a pool for up to two guests.

This 700 sq ft apartment in Chicago's West Loop offers a prime location, just a 5 to 10-minute walk from Union Station and close to Randolph Street's "Restaurant Row" and Fulton Market.
Guests can enjoy a comfortable stay with a queen-sized bed, in-apartment laundry, and building amenities including a doorman and a swimming pool with a pool, perfect for a relaxing getaway.

Located in Chicago's downtown Loop, this apartment is under 0.6 miles from Willis Tower and near Union Station.
Enjoy this 790 square feet, 1-bedroom apartment with an indoor swimming pool and hot tub, perfect for your pool getaway in Chicago.

Enjoy an indoor swimming pool at this downtown Chicago apartment, located less than 0.6 miles from Willis Tower and near Union Station, the Art Institute of Chicago, and Grant Park.
This 950 square feet, 1-bedroom apartment accommodates up to 4 guests and features a kitchen with a fridge, microwave, and dishwasher, plus a fitness center and hot tub for your enjoyment.

Enjoy a prime River North location in downtown Chicago, just minutes from Magnificent Mile shopping and close to riverside parks.
This 540 sq ft studio apartment accommodates up to 4 guests and features a swimming pool, a kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.

Centrally located in Chicago's city center, this studio is just 0.6 miles from Willis Tower and a 16-minute walk to Union Station.
This studio offers a comfortable stay for up to 4 guests, featuring a fully equipped kitchen, air conditioning, and the convenience of an indoor swimming pool and hot tub.

Located in Chicago's West Loop, this apartment is just 500 feet from Union Station and close to Fulton Market and downtown attractions.
This 1080 square foot apartment accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen and in-apartment laundry, plus building amenities including a swimming pool with a pool.

Enjoy stunning skyline views from this prime River North apartment, located at Superior & Lasalle, a convenient base for exploring Chicago, just 500 feet from the Magnificent Mile.
This fully furnished 1-bedroom apartment offers the perfect urban getaway with access to a seasonal outdoor swimming pool, a 24-hour gym, and an on-site business center, ideal for travelers seeking an apartment with a pool.