Waterfront holiday rentals in Downtown Chicago
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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
Rental unit in Chicago
The Holiday House by the Lake! 2br/2bth
Rental unit in Evanston
New renovation|1BR|Stylish|Modern|Next to the Lake
Rental unit in Chicago
Elegant 2-bed/2-bath in the heart of Uptown
Rental unit in Chicago
Lovely Lake Side Apartment
Rental unit in Chicago
Executive Apartment on Lake Michigan with parking
Rental unit in Evanston
MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Rental unit in Chicago
NVCLL Chicago
Rental unit in Chicago
Boutique Flat in Lincoln Park with Free Parking!
Waterfront house rentals
Home in Des Plaines
Exotic House - Few minutes from O'Hare and Chicago
Home in Chicago
'22 CasaNova Modern City Living
Home in Highland Park
Witness Sunrise Over Lake Michigan
Home in Chicago
Beautiful 3 Bedroom TownHome in Rogers Park
Home in Chicago
Lake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Chicago
Cozy home w/ 4 bedrooms in Bridgeport Chicago
Home in Prospect Heights
Classy Lakefront Home w/ Charcoal Grill & Deck!
Home in Des Plaines
House 1 minute from O'hare Airport
Waterfront apartment rentals
Apartment in Chicago
Bronzeville Tribe Palace Loft
Apartment in Chicago
PING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Apartment in Chicago
Cozy Studio 1BR Apt near the lake on the Northside
Apartment in Chicago
Lovely condo studio
Apartment in Chicago
Spacious Wicker Park Hideaway with Parking!
Apartment in Chicago
Where you want to BE! Stylish, Comfy, Luxe
Apartment in Chicago
Lovely 1 Bedroom with Fireplace and Home Office
Apartment in Calumet City
Chicago/Grant Park/Solider Field
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a hot tub Downtown Chicago
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- Fitness-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
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- Townhouse rentals Downtown Chicago
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- Loft rentals Downtown Chicago
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- Monthly Rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Hotel rentals Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
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