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
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Popular amenities for waterfront rentals in Downtown Chicago
Waterfront apartment rentals
Rental unit in Chicago
4.93 out of 5 average rating, 30 reviewsSheridan Beach Apartment
Rental unit in Chicago
4.75 out of 5 average rating, 16 reviews2b2b by Water Tower and the Lake
Rental unit in Chicago
4.76 out of 5 average rating, 117 reviewsCozy 1 BR Apartment in South Loop
Rental unit in Chicago
4.85 out of 5 average rating, 61 reviewsElegant 2-bed/2-bath in the heart of Uptown
Rental unit in Chicago
4.6 out of 5 average rating, 144 reviewsBoutique Flat in Lincoln Park with Free Parking
Rental unit in Chicago
4.7 out of 5 average rating, 90 reviewsModern Lakefront Retreat with Breathtaking Views!
Rental unit in Chicago
4.54 out of 5 average rating, 46 reviewsHUGE & BRAND NEW BEACH Apartment is Ready For You!
Rental unit in Evanston
4.86 out of 5 average rating, 49 reviewsModern|Spacious|New Renovation|1BR|Evanston
Waterfront house rentals
Home in Chicago
5 out of 5 average rating, 6 reviewsGem Near Hyde Park/McCormick Place
Home in Lisle
4.74 out of 5 average rating, 39 reviewsBeautiful and secluded 3 bedroom ranch style home
Home in Prospect Heights
4.92 out of 5 average rating, 48 reviewsLakefront Home w/ Deck & Grill in Prospect Heights
Home in Chicago
4.9 out of 5 average rating, 48 reviewsCasaNova Modern City Living
Home in Downers Grove
4.96 out of 5 average rating, 23 reviewsLakefront Getaway Home! Lots of Fun! Win.Discount$
Home in Chicago
4.84 out of 5 average rating, 73 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Des Plaines
4.59 out of 5 average rating, 27 reviewsHouse 1 minute from O'hare Airport
Home in Westmont
4.89 out of 5 average rating, 28 reviewsCozy 5-bedroom with lake views and spacious deck
Waterfront apartment rentals
Apartment in Chicago
4.7 out of 5 average rating, 200 reviewsStudio flat in the heart of Chicago's Gold Coast
Apartment in Chicago
4.89 out of 5 average rating, 149 reviewsMARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Apartment in Chicago
4.86 out of 5 average rating, 14 reviewsLovely 1 Bedroom with Fireplace and Home Office
Apartment in Chicago
5 out of 5 average rating, 55 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Apartment in Chicago
4.79 out of 5 average rating, 19 reviewsSpacious Wicker Park Hideaway with Parking!
Apartment in Chicago
4.84 out of 5 average rating, 76 reviewsRiver North Hideaway w/Amazing Views and Parking
Apartment in Chicago
4.93 out of 5 average rating, 90 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
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