Waterfront holiday rentals in Downtown Chicago
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Downtown Chicago
Guests agree: These waterfront accommodation options 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 Downtown Chicago waterfront rentals
Waterfront apartment accommodation
Apartment in Chicago
4.81 out of 5 average rating, 90 reviewsCozy 1 BR Apartment in South Loop
Apartment in Evanston
4.94 out of 5 average rating, 47 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
Apartment in Chicago
4.94 out of 5 average rating, 50 reviewsThe Holiday House by the Lake! 2br/2bth
Apartment in Chicago
4.86 out of 5 average rating, 35 reviewsElegant 2-bed/2-bath in the heart of Uptown
Apartment in Chicago
4.94 out of 5 average rating, 127 reviewsExecutive Apartment on Lake Michigan with parking
Apartment in Evanston
4.79 out of 5 average rating, 133 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Apartment in Chicago
4.77 out of 5 average rating, 13 reviewsNVCLL Chicago
Apartment in Chicago
4.6 out of 5 average rating, 133 reviewsBoutique Flat in Lincoln Park with Free Parking!
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 56 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
Home in Chicago
4.89 out of 5 average rating, 35 reviews'22 CasaNova Modern City Living
Home in Highland Park
4.93 out of 5 average rating, 41 reviewsWitness Sunrise Over Lake Michigan
Home in Chicago
4.83 out of 5 average rating, 63 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Chicago
4.72 out of 5 average rating, 25 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Home in Chicago
4.64 out of 5 average rating, 11 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
Home in Prospect Heights
4.93 out of 5 average rating, 44 reviewsClassy Lakefront Home w/ Charcoal Grill & Deck!
Home in Des Plaines
4.44 out of 5 average rating, 9 reviewsHouse 1 minute from O'hare Airport
Waterfront condo accommodation
Condo in Chicago
4.66 out of 5 average rating, 175 reviewsStudio flat in the heart of Chicago's Gold Coast
Condo in Chicago
4.86 out of 5 average rating, 21 reviewsBronzeville Tribe Palace Loft
Condo in Chicago
4.92 out of 5 average rating, 12 reviewsCozy Studio 1BR Apt near the lake on the Northside
Condo in Chicago
4.79 out of 5 average rating, 19 reviewsLovely condo studio
Condo in Chicago
4.73 out of 5 average rating, 15 reviewsSpacious Wicker Park Hideaway with Parking!
Condo in Chicago
5.0 out of 5 average rating, 50 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Condo in Chicago
4.82 out of 5 average rating, 11 reviewsLovely 1 Bedroom with Fireplace and Home Office
Condo 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
- Kid-friendly rentals Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a patio Downtown Chicago
- Condo rentals Downtown Chicago
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- Rentals with breakfast Downtown Chicago
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- Townhouse rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Loft rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Apartment rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Rentals with pools Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Waterfront rentals Milwaukee
- Waterfront rentals Illinois
- Waterfront rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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