Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop Pool available 
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8.5 (81 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Best Price Match Chicago Vacation Homes and Villas with Pools
Find Luxury Places to Stay Near Chicago with a Swimming Pool. Find pool in Chicago, Illinois.
Pool
Only stays with pool access are shown on this page
15 stays
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile Pool available Best Price Match
9.2 (59 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • 359m from Water Tower Place
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Fulbrix Bright Designer Apartments with West Loop Views Pool available Best Price Match
9.5 (50 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near West Side • 1.3km from United Center
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Aurelien Spacious Apartments in the Heart of Gold Coast Pool available Best Price Match
8.9 (58 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • 659m from 360 CHICAGO
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K2 Sky High Apartments with Stunning Chicago Views in West Loop Pool available Best Price Match
9.5 (24 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
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Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop Pool available Best Price Match
8.4 (51 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
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Foundry Unmatched Skyline Views at Lincoln Park Pool available Best Price Match
9.3 (17 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago River North • 2.1km from Lincoln Park Zoo
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Lux Apts with Lake Views and Top Amenities Pool available Best Price Match
9.9 (26 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
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Premier Penthouses and Apartment with Captivating Views of Millennium Park Pool available Best Price Match
9.4 (8 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
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Uptown Gem Pool available Best Price Match
9.3 (15 Reviews) Apartment
The entire place is yours • 42 m² size • Free parking
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South Loop Rooftop With In and Out Parking 3 Pool available Best Price Match
9.2 (5 Reviews) Apartment
The entire place is yours • 82 m² size • Swimming pool
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Jeffjack Heated Pool Penthouse in Chicago's West Loop Pool available Best Price Match
8.0 (9 Reviews) Apartment
The entire place is yours • 1000 m² size • Private parking
Chicago Near West Side • 225m from Chicago Union Station
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South Loop Rooftop With In and Out Parking 2 Pool available Best Price Match
9.7 (3 Reviews) Apartment
The entire place is yours • 82 m² size • Swimming pool
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South Loop Rooftop With In & Out Parking 1 Pool available Best Price Match
8.5 (4 Reviews) Apartment
The entire place is yours • 82 m² size • Swimming pool
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Sophisticated 3BR Suite - New Modern and Luxurious Pool available Best Price Match
7.7 (7 Reviews) Apartment
The entire place is yours • 139 m² size • Outdoor swimming pool
Chicago Near West Side • 1.3km from United Center
Best Price Match About Chicago Vacation Rentals with Pools on NearbyHoliday
Looking for pool in Chicago? Compare top options in Illinois.
Find Chicago Rentals, Hotels, and Resorts with Swimming Pools.
Discover 15 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Chicago that feature indoor, outdoor, or private pools.
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NearbyHoliday can help you find hotels, resorts, and rentals near many of Chicago's top attractions, neighborhoods, and points of interest. Find pool in Chicago for easier access to nearby attractions.