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
5 out of 5 average rating, 17 reviews3BR Luxury Modern Apartment
Apartment in Chicago
4.98 out of 5 average rating, 41 reviewsCozy Chicago Apartment next to the River
Apartment in Chicago
4.74 out of 5 average rating, 19 reviews2b2b by Water Tower and the Lake
Apartment in Chicago
4.79 out of 5 average rating, 33 reviewsModern Cozy Top Floor Duplex near Wrigley
Apartment in Chicago
4.76 out of 5 average rating, 117 reviewsCozy 1 BR Apartment in South Loop
Apartment in Evanston
4.92 out of 5 average rating, 74 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
Apartment in Chicago
4.71 out of 5 average rating, 93 reviewsModern Lakefront Retreat with Breathtaking Views!
Apartment in Chicago
4.54 out of 5 average rating, 46 reviewsHUGE & BRAND NEW BEACH Apartment is Ready For You!
Waterfront house rentals
Home in Prospect Heights
4.9 out of 5 average rating, 49 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 Chicago
4.71 out of 5 average rating, 17 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
Home in Chicago
4.84 out of 5 average rating, 74 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Des Plaines
4.66 out of 5 average rating, 32 reviewsHouse 1 minute from O'hare Airport
Home in Westmont
4.9 out of 5 average rating, 29 reviewsCozy 5-bedroom with lake views and spacious deck
Home in Des Plaines
4.79 out of 5 average rating, 185 reviewsExotic House - Few minutes from O'Hare and Chicago
Home in Chicago
4.61 out of 5 average rating, 36 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
Waterfront condo accommodation
Condo in Chicago
4.89 out of 5 average rating, 151 reviewsMARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Burbank
New place to stayIconic Style, Charming Lake View
Condo in Chicago
4.87 out of 5 average rating, 15 reviewsLovely 1 Bedroom with Fireplace and Home Office
Condo in Chicago
4.79 out of 5 average rating, 19 reviewsSpacious Wicker Park Hideaway with Parking!
Condo in Chicago
5 out of 5 average rating, 55 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Condo in Chicago
4.94 out of 5 average rating, 97 reviewsModern MAG Mile 2BD/2BA (+Parking/Rooftop)
Condo in Chicago
4.85 out of 5 average rating, 81 reviewsRiver North Hideaway w/Amazing Views and Parking
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Beachfront rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- House rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with pools Downtown Chicago
- Hotel rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a fire pit 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
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- 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
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
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- Nature and outdoors United States
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- Things to do Illinois
- Art and culture Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Food and drink Cook County
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Sightseeing Downtown Chicago
- Food and drink Downtown Chicago