Waterfront vacation 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.
Vacation rentals for every style
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Popular amenities for Downtown Chicago waterfront rentals
Waterfront apartment rentals
Apartment in Chicago
4.82 out of 5 average rating, 88 reviewsCozy 1 BR Apartment in South Loop
Jul 21 – 28
Apartment in Evanston
4.86 out of 5 average rating, 29 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun 18 – 25
Apartment in East Rogers Park
4.93 out of 5 average rating, 46 reviewsThe Holiday House by the Lake! 2br/2bth
Nov 23 – 30
Apartment in Chicago
4.87 out of 5 average rating, 30 reviewsElegant 2-bed/2-bath in the heart of Uptown
Mar 15 – 22
Apartment in East Rogers Park
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
Apr 20 – 27
Apartment in Evanston
4.78 out of 5 average rating, 128 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Jul 7 – 14
Apartment in Chicago
4.78 out of 5 average rating, 9 reviewsNVCLL Chicago
Dec 22 – 29
Apartment in Chicago
4.6 out of 5 average rating, 133 reviewsBoutique Flat in Lincoln Park with Free Parking!
Dec 22 – 29
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 54 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Oct 18 – 25
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
Oct 4 – 11
Home in Chicago
4.74 out of 5 average rating, 23 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Oct 26 – Nov 2
Home in Chicago
4.82 out of 5 average rating, 61 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Dec 31 – Jan 7
Home in Westmont
4.89 out of 5 average rating, 18 reviewsCozy 5-bedroom with lake views and spacious deck
Feb 21 – 28
Home in Chicago
4.6 out of 5 average rating, 10 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
Jan 24 – 31
Home in Prospect Heights
4.93 out of 5 average rating, 44 reviewsClassy Lakefront Home w/ Charcoal Grill & Deck!
Dec 3 – 10
Home in Des Plaines
4.43 out of 5 average rating, 7 reviewsHouse 1 minute from O'hare Airport
Nov 11 – 18
Waterfront condo rentals
Condo in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
May 10 – 17
Condo in Chicago
4.92 out of 5 average rating, 64 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Nov 2 – 9
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Dec 14 – 21
Condo in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
Jan 3 – 10
Condo in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
Nov 21 – 28
Condo in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Aug 8 – 15
Condo in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
Jan 17 – 24
Condo in Calumet City
4.89 out of 5 average rating, 9 reviewsChicago/Grant Park/Solider Field
Jan 23 – 30
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