Compare Vacation Rentals with Pools in 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.

Located in Downtown Chicago's New Eastside, this apartment is just a short walk to Michigan Avenue and Navy Pier, offering stunning balcony views over the city skyline.
This 850 sq ft, 1-bedroom apartment comfortably sleeps 2 and features a fully equipped kitchen, in-apartment laundry, and building amenities including a swimming pool, game room, and sauna, making it a perfect getaway with a pool.

Just 0.6 miles from Willis Tower, this studio is located in Chicago's city center and a 15-minute walk to Millennium Park, offering convenient access to attractions like the Art Institute of Chicago.
This studio accommodation features an indoor swimming pool, a fitness center, and a fully equipped kitchen, perfect for travelers seeking a getaway with a pool and ample space at 580 square feet.

Enjoy a 2-bedroom, 1-bathroom apartment in Chicago, featuring a fenced backyard with a fire pit and a seasonal above-ground swimming pool, perfect for summer getaways with a pool.
This renovated basement apartment offers Roku TV, dimmable lighting, and is conveniently located in a 4-unit building, providing a private and comfortable stay for up to 4 guests with pets allowed.

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.

Enjoy city views from the rooftop swimming pool at this Chicago apartment, conveniently located in the West Loop, just 0.9 miles from Willis Tower and 1.2 miles from Millennium Park.
This 460 square foot, 1-bedroom apartment accommodates up to 3 guests and offers a fully equipped kitchen, free WiFi, an on-site gym, and is pet-friendly, providing a comfortable stay with a pool.

Directly across from a park, swimming pool, and tennis courts, this Forest Park house offers excellent access to the Roos Recreation Center.
This dog-friendly house, featuring a fenced yard and doggy door, is a 5-minute walk to the Harlem Blue Line Station for transit to downtown Chicago and O'Hare Airport, and includes a dedicated workspace and modern amenities for up to 4 guests.

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.

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.

Located in Chicago's Fulton Market district, this apartment is just a short walk to the Chicago River Walk, Willis Tower, and Soho House Chicago.
This family-friendly apartment offers 2 bathrooms, accommodates up to 4 guests, and boasts a seasonal outdoor swimming pool, hot tub, and fitness center for an excellent getaway with a pool.

Just a 15-minute walk from Montrose Beach, this Uptown Chicago apartment offers convenient access to Wrigley Field (1.7 miles) and Loyola University Chicago (2.5 miles).
This family-friendly apartment, complete with an indoor swimming pool and a private balcony, boasts a fully equipped kitchen, complimentary WiFi, and an on-site restaurant, making it an ideal choice for those seeking a getaway with a pool.

Experience breathtaking lake and city views from this sky-high apartment in downtown Chicago, just a 5-minute walk from Grant Park and a 10-minute walk from the Shedd Aquarium.
This spacious 6-bedroom apartment accommodates up to 15 guests and features a luxurious indoor and outdoor swimming pool, a fitness center with a basketball court, a game room, and a golf simulator, perfect for a 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 a studio apartment in Chicago's Streeterville neighborhood, just a 5-minute walk from The Loop and close to Navy Pier and Michigan Avenue shopping.
This well-appointed studio offers 650 square feet of living space, accommodates up to 2 guests, and features a modern kitchen, smart TV, and access to a swimming pool.

Enjoy high-floor city views from this studio in Chicago's Streeterville neighborhood, just a 5-minute walk from The Loop and close to Lake Michigan.
This elegantly furnished studio, perfect for two guests, features a fully equipped kitchen and offers access to an on-site swimming pool, making it an ideal getaway with a pool.

Experience Chicago from this luxury apartment with a swimming pool, offering exclusive access to a clubhouse with stunning city views and a private conference room, all just steps from major city attractions.
This 1-bedroom, 1-bathroom apartment accommodates up to 3 guests and features a fully equipped kitchen with premium appliances, a coffee bar, in-unit laundry, 500 Mbps WiFi, and 65” Smart TVs, complemented by a 24/7 fitness center and concierge service for a seamless stay.

Stunning city views highlight this one-bedroom apartment located in Chicago's River North neighborhood, just a 5-minute walk from Michigan Avenue shopping, the Merchandise Mart, and The Loop.
This 750 sq ft apartment offers a fully equipped kitchen, in-unit laundry, and access to a building swimming pool, perfect for travelers seeking a relaxing getaway with a pool.

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.

Enjoy a downtown Chicago apartment with a pool in the prime Lakeshore East neighborhood, just steps from the lakefront, Michigan Avenue shopping, and Millennium Park.
This 1-bedroom, 1-bathroom apartment accommodates up to 4 guests and offers a fitness center, jacuzzi, and air conditioning for a comfortable stay.

Located in Chicago's West Loop Gate neighborhood, this apartment offers convenient access to downtown attractions such as the Merchandise Mart and Cloud Gate, just a short distance away.
Enjoy this furnished one-bedroom apartment with a fully equipped kitchen, in-unit laundry, and access to building amenities including a swimming pool, fitness center, and BBQ area, perfect for travelers seeking a getaway with a pool.

Located in the River North district, this apartment is a 5-minute walk to Merchandise Mart and The Loop, with Michigan Avenue shopping nearby.
This 830 sq ft apartment, accommodating up to 2 guests, features a full kitchen, in-unit laundry, and a swimming pool, perfect for your Chicago getaway with a pool.