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
4.86 out of 5 average rating, 7 reviewsSheridan Beach Apartment
Jan 16 – 23
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
Jul 20 – 27
Apartment in Evanston
4.86 out of 5 average rating, 29 reviewsModern|Spacious|New Renovation|1BR|Evanston
Jun 18 – 25
Apartment in Chicago
4.93 out of 5 average rating, 46 reviewsThe Holiday House by the Lake! 2br/2bth
Apr 3 – 10
Apartment in Chicago
4.86 out of 5 average rating, 29 reviewsElegant 2-bed/2-bath in the heart of Uptown
Jan 15 – 22
Apartment in Lisle
4.65 out of 5 average rating, 78 reviewsTranquility and comfort in private condo
Aug 11 – 18
Apartment in Chicago
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
Jan 3 – 10
Apartment in Evanston
4.78 out of 5 average rating, 127 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Aug 9 – 16
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 53 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Oct 23 – 30
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
Oct 16 – 23
Home in Deerfield
4.96 out of 5 average rating, 26 reviewsLake Forest Country Estate
May 26 – Jun 2
Home in Schaumburg
4.89 out of 5 average rating, 44 reviewsSprawling private fenced home with pond view!
May 26 – Jun 2
Home in Chicago
4.82 out of 5 average rating, 61 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Nov 4 – 11
Home in Westmont
4.89 out of 5 average rating, 18 reviewsCozy 5-bedroom with lake views and spacious deck
Feb 26 – Mar 5
Home in Chicago
4.74 out of 5 average rating, 23 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Feb 20 – 27
Home in Chicago
4.67 out of 5 average rating, 9 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
Sep 13 – 20
Waterfront condo rentals
Condo in Chicago
4.92 out of 5 average rating, 62 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
May 10 – 17
Condo in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
Nov 16 – 23
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Dec 11 – 18
Condo in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
Dec 13 – 20
Condo in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
Nov 11 – 18
Condo in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Aug 20 – 27
Condo in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
Jul 10 – 17
Condo in Calumet City
4.89 out of 5 average rating, 9 reviewsChicago/Grant Park/Solider Field
Jan 25 – Feb 1
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