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
Flat in Chicago
4.82 out of 5 average rating, 88 reviewsCozy 1 BR Apartment in South Loop
Flat in Chicago
4.94 out of 5 average rating, 47 reviewsThe Holiday House by the Lake! 2br/2bth
Flat in Chicago
4.87 out of 5 average rating, 31 reviewsElegant 2-bed/2-bath in the heart of Uptown
Flat in Evanston
4.96 out of 5 average rating, 45 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
Flat in Lisle
4.65 out of 5 average rating, 80 reviewsTranquility and comfort in private condo
Flat in Edgewater
4.17 out of 5 average rating, 6 reviewsLovely Lake Side Apartment
Flat in Chicago
4.94 out of 5 average rating, 125 reviewsExecutive Apartment on Lake Michigan with parking
Flat in Evanston
4.78 out of 5 average rating, 130 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Waterfront house rentals
Home in Chicago
4.88 out of 5 average rating, 33 reviews'22 CasaNova Modern City Living
Home in Deerfield
4.96 out of 5 average rating, 26 reviewsLake Forest Country Estate
Home in Chicago
4.82 out of 5 average rating, 61 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Chicago
4.74 out of 5 average rating, 23 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Home in Chicago
4.6 out of 5 average rating, 10 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
Home in Westmont
4.89 out of 5 average rating, 19 reviewsCozy 5-bedroom with lake views and spacious deck
Home in Prospect Heights
4.93 out of 5 average rating, 44 reviewsClassy Lakefront Home w/ Charcoal Grill & Deck!
Home in Lisle
4.72 out of 5 average rating, 36 reviewsBeautiful and secluded 3 bedroom ranch style home
Waterfront apartment rentals
Apartment in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
Apartment in Chicago
4.92 out of 5 average rating, 64 reviewsPING-PONG Free PARKiNG 10 min-Downtown Sleeps 10
Apartment in Chicago
4.9 out of 5 average rating, 10 reviewsCozy Studio 1BR Apt near the lake on the Northside
Apartment in Chicago
4.76 out of 5 average rating, 17 reviewsLovely condo studio
Apartment in Chicago
4.77 out of 5 average rating, 13 reviewsSpacious Wicker Park Hideaway with Parking!
Apartment in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Apartment in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
Apartment in Calumet City
4.89 out of 5 average rating, 9 reviewsChicago/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 an EV charger Downtown Chicago
- Rentals with beach access Downtown Chicago
- House rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with lake access Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
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