Compare Vacation Rentals with Pools in Chicago

This 2-bedroom apartment is located in Chicago, offering convenient access to attractions like the United Center (7.4 miles) and Lincoln Park Zoo (7.6 miles), with Wrigley Field (7.8 miles) also nearby.
Enjoy a comfortable stay in this 1080 square foot apartment, complete with a fully equipped kitchen, air conditioning, and a backyard with a grill, though this particular listing does not feature a swimming pool.

Experience Chicago's Printer's Row from this modern apartment, just a short walk to local cafes, restaurants, and Grant Park.
This 3-bedroom, 3-bathroom unit offers a fully equipped kitchen, sleek furnishings, and access to a seasonal rooftop swimming pool with stunning skyline views.

Centrally located in downtown Chicago, this apartment is just one block from an 'L' train stop and within walking distance of Millennium Park, the Bean, Navy Pier, Riverwalk, and museum campus.
This apartment offers excellent city views and access to building amenities including a swimming pool, hot tub, and fitness center, perfect for a getaway with a pool.

Located in Chicago's Near North Side, this apartment offers stunning city views from its private balcony and terrace, with proximity to a fire and police station.
This one-bedroom apartment features a fully equipped kitchen, in-apartment laundry, and access to a building swimming pool, perfect for travelers seeking a getaway with a pool.

Located in Chicago's South Loop, this studio offers convenient access to the city's attractions.
Enjoy a comfortable stay in this studio with a swimming pool, perfect for unwinding after exploring downtown Chicago, featuring a fully equipped kitchen and on-site laundry.

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 a prime Downtown Chicago location, just 500 feet from Michigan Avenue and State Street, with direct access to the Red Line metro at Grand Station (1 minute walk) and Chicago Station (8 minutes walk) for exploring the city.
This 730 square foot apartment accommodates 2 guests and features a private balcony, onsite covered parking, and access to a communal swimming pool, perfect for a relaxing getaway.

This one-bedroom apartment is located in Chicago's South Loop district, offering convenient access to city attractions.
Enjoy this family-friendly apartment with a swimming pool, fitness center, and fully equipped kitchen, perfect for a comfortable stay with a guest capacity of two.

Enjoy Chicago city views from this luxurious 2-bedroom apartment, located just a block from the 'L' train and within walking distance of Millennium Park, the Bean, Navy Pier, Riverwalk, and museum campus.
This apartment offers a premium stay with a swimming pool, hot tub, and fitness center, perfect for travelers seeking a getaway with a pool in Chicago.

Enjoy a prime River North location in Chicago, just steps from world-class dining and entertainment.
This stylish 1-bedroom apartment offers a comfortable stay with a swimming pool, fitness center, and in-unit WiFi, perfect for travelers seeking accommodations with a pool.

Located in Chicago's historic Printer's Row district, this modern apartment is a short distance from downtown attractions.
This spacious 3-bedroom, 3-bathroom apartment accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, and access to a seasonal swimming pool with panoramic city views, perfect for a getaway with a pool.

Located in Chicago's Loop district, this apartment is just a 14-minute walk from Millennium Park and within 700 yards of the city center, offering a prime location for exploring major attractions like Willis Tower and CIBC Theatre.
This apartment features an indoor swimming pool, air conditioning, complimentary Wi-Fi, and private parking, with a spacious 1460 square feet of living area and two bathrooms.

Located in Chicago's West Loop, this apartment is a 5-10 minute walk to Union Station and close to Restaurant Row and Fulton Market.
This one-bedroom apartment offers 690 square feet of living space and features a swimming pool, making it ideal for travelers seeking a getaway with a pool.

Located in Chicago's Downtown district, Aurelien Spacious Apartments is just 0.7 miles from the city center and a short distance from Oak Street Beach (0.3 miles), Water Tower Chicago (0.4 miles), and 360 Chicago (0.4 miles).
This family-friendly apartment offers a rooftop swimming pool, fitness center, and private parking, along with air-conditioned units featuring a well-equipped kitchen and free WiFi for a complete getaway with a pool.

Located in Chicago's Loop district, this apartment offers stunning high-floor city views and immediate access to the urban core.
This 1-bedroom apartment sleeps 2 and features a fully equipped kitchen, in-apartment laundry, and a swimming pool for guests seeking a getaway with a pool.

This apartment offers an indoor swimming pool and is located just 400 feet from Millennium Station and Millennium Park in Chicago.
Enjoy a terrace with park views, a full kitchen, and on-site parking, with easy access to attractions like Cloud Gate – The Bean and the Chicago Symphony Orchestra.

Enjoy a prime West Loop location in Chicago, just a short walk from the city's best attractions and dining.
This one-bedroom apartment offers modern furnishings, in-apartment laundry, and building amenities including a swimming pool, perfect for a relaxing getaway with a pool.

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.

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 stunning one-bedroom suite with a private balcony in Chicago's River North district, offering exceptional city views and convenient access to downtown attractions.
This resort features a seasonal outdoor heated swimming pool and hot tub, perfect for relaxation, alongside a state-of-the-art fitness center and 24/7 concierge services for a memorable stay.

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.

This one-bedroom apartment in Chicago's Streeterville district is located just a 5-minute walk from The Loop, placing you within easy reach of Michigan Avenue shopping and Navy Pier.
Enjoy a comfortable stay in this 740 square foot apartment with a fully equipped kitchen and convenient in-apartment laundry, all while having access to a building swimming pool for a perfect getaway.

This Near West Side condo is located 3 miles from downtown Chicago attractions like Millennium Park, Shedd Aquarium, and the Art Institute, and is conveniently situated just 3 blocks from the train station.
Enjoy 1250 square feet of living space in this pet-friendly apartment with a private 44’ patio, in-unit laundry, and access to a community swimming pool, offering a perfect getaway with a pool.

Located in Chicago's Near North Side, this apartment is just 0.3 miles from Navy Pier and offers direct city skyline views, placing you steps from the Miracle Mile and Museum of Contemporary Art.
This 560 sq ft, 1-bedroom apartment comfortably accommodates 2 guests and features a swimming pool, in-unit laundry, and a fully equipped kitchen, perfect for a getaway with a pool.

Enjoy a Chicago getaway with this fully furnished 1-bedroom apartment, featuring an outdoor swimming pool and located just a short walk from numerous restaurants.
This apartment offers a king-sized bed, a full kitchen with stainless steel appliances, high-speed WiFi, and on-site parking is available for an additional fee.

This Cook County apartment is located near Chicago landmarks such as the Merchandise Mart and Cloud Gate, offering easy access to Lincoln Park Zoo and the Field Museum of Natural History, and is conveniently situated for events at Wrigley Field or the United Center.
Enjoy year-round swimming in the indoor heated pool, a dedicated game room with a TV, and two living rooms, all within this 3-bedroom apartment that accommodates up to 7 guests and allows pets.

Enjoy this one-bedroom apartment located in The Loop, Chicago's downtown district, just a short distance from the Willis Tower and the Art Institute of Chicago.
This stylish apartment offers 650 square feet of living space and includes a swimming pool, perfect for unwinding after exploring the city.

Enjoy a stay in a Chicago district known for its convenient access to key attractions, offering a sophisticated urban experience.
This apartment, featuring a king bed and a sofa bed for up to 3 guests, boasts a spacious 650 sqft layout and a fully equipped kitchen, all complemented by a fantastic heated swimming pool for your enjoyment.

This apartment is located in Chicago's Theater District, steps from Millennium Park and major attractions, offering excellent public transit access for exploring the city.
Enjoy a comfortable stay in this pet-friendly apartment, featuring a full kitchen, air conditioning, and a suite of amenities including a swimming pool, fitness center, and sauna, perfect for business travel or city getaways.