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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
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Rental unit in Chicago
4.78 out of 5 average rating, 101 reviewsCozy 1 BR Apartment in South Loop
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Rental unit in Evanston
4.86 out of 5 average rating, 36 reviewsModern|Spacious|New Renovation|1BR|Evanston
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Rental unit in Chicago
4.94 out of 5 average rating, 54 reviewsThe Holiday House by the Lake! 2br/2bth
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Rental unit in Chicago
4.89 out of 5 average rating, 44 reviewsElegant 2-bed/2-bath in the heart of Uptown
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Rental unit in Chicago
4.79 out of 5 average rating, 33 reviewsModern Cozy Top Floor Duplex near Wrigley
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Rental unit in Chicago
4.6 out of 5 average rating, 133 reviewsBoutique Flat in Lincoln Park with Free Parking!
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Rental unit in Chicago
4.5 out of 5 average rating, 18 reviewsLovely Lake Side Apartment
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Rental unit in Chicago
5 out of 5 average rating, 8 reviewsLux 4BR Lakeshore: W/Rftop Book Now!
Waterfront house rentals
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Home in Chicago
5 out of 5 average rating, 63 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
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Home in Chicago
4.9 out of 5 average rating, 41 reviewsCasaNova Modern City Living
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Home in Chicago
New place to staySpacious house patio/parking
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Home in Des Plaines
4.82 out of 5 average rating, 170 reviewsExotic House - Few minutes from O'Hare and Chicago
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Home in Chicago
4.83 out of 5 average rating, 65 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
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Home in Chicago
4.68 out of 5 average rating, 28 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
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Home in Downers Grove
5 out of 5 average rating, 5 reviewsSpacious Lakefront Getaway Home! Kayak & More!
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Home in Westmont
4.91 out of 5 average rating, 23 reviewsCozy 5-bedroom with lake views and spacious deck
Waterfront apartment rentals
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Apartment in Chicago
4.97 out of 5 average rating, 69 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
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Apartment in Chicago
4.87 out of 5 average rating, 93 reviewsUpscale Penthouse Private Balconies Amazing Views
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Apartment in Chicago
4.74 out of 5 average rating, 23 reviewsLovely condo studio
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Apartment in Chicago
4.85 out of 5 average rating, 27 reviewsBronzeville Tribe Palace Loft
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Apartment in Chicago
4.92 out of 5 average rating, 13 reviewsCozy Studio 1BR Apt near the lake on the Northside
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Apartment in Chicago
4.82 out of 5 average rating, 11 reviewsLovely 1 Bedroom with Fireplace and Home Office
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Apartment in Chicago
4.76 out of 5 average rating, 17 reviewsSpacious Wicker Park Hideaway with Parking!
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Apartment in Chicago
5 out of 5 average rating, 52 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Destinations to explore
- Milwaukee Holiday rentals
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- Lake Michigan Beach Holiday rentals
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