
Waterfront holiday rentals in Downtown Chicago
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Downtown Chicago
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Downtown Chicago
Waterfront apartment rentals

Luxurious Lincoln Park Home with Gourmet Kitchen

Sheridan Beach Apartment

The Wine Down

3BR Luxury Modern Apartment

Cozy Chicago Apartment next to the River

2b2b in River North

Cozy 1BR in South Loop | Convenience in the City

Elegant 2-bed/2-bath in the heart of Uptown
Waterfront house rentals

Renovated space in a historic row house.

Lakefront Prospect Heights Home: Ice Fish On-Site

CasaNova Modern City Living

Lakefront Getaway Home! Amazing View! Hot tub! Ski

Comfortable private room near Lake and transit.

Spacious house patio/free parking

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

House 1 minute from O'hare Airport
Waterfront apartment rentals

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

HUGE Modern, 1BD Home Office, Chef's Kitchen Patio

Where you want to BE! Stylish, Comfy, Luxe

Spacious Wicker Park Hideaway with Parking!

River North Hideaway w/Amazing Views and Parking

Bronzeville Tribe Palace Loft

Breathtaking water view condo
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
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- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
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- Rentals with breakfast Downtown Chicago
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- Apartment rentals Downtown Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Six Flags Great America
- Skokie Country Club
- Promontory Point
- 875 North Michigan Avenue
- Flossmoor Golf Club
- Odyssey Fun World
- Moraine Hills State Park
- Washington Park Zoo
- Chicago History Museum
- Chicago Golf Club
- The 606
- Lincoln Park
- Things to do Downtown Chicago
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