
Waterfront holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Downtown Chicago
Waterfront apartment rentals

Flat in Chicago
4.93 out of 5 average rating, 30 reviewsSheridan Beach Apartment

Flat in Chicago
5 out of 5 average rating, 3 reviewsThe Wine Down

Flat in Chicago
4.98 out of 5 average rating, 43 reviewsCozy Chicago Apartment next to the River

Flat in Chicago
5 out of 5 average rating, 19 reviews3BR Luxury Modern Apartment

Flat in Chicago
4.77 out of 5 average rating, 22 reviews2b2b by Water Tower and the Lake

Flat in Chicago
4.86 out of 5 average rating, 65 reviewsElegant 2-bed/2-bath in the heart of Uptown

Flat in Evanston
4.92 out of 5 average rating, 77 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake

Flat in Chicago
4.71 out of 5 average rating, 96 reviewsModern Lakefront Retreat with Breathtaking Views!
Waterfront house rentals

Home in Chicago
4.25 out of 5 average rating, 4 reviewsSpacious 2 BR in Historic South Shore near Train!

Home in Prospect Heights
4.9 out of 5 average rating, 52 reviewsLakefront Prospect Heights Home: Ice Fish On-Site

Home in Schaumburg
4.91 out of 5 average rating, 54 reviewsSprawling private fenced home with pond view!

Home in Chicago
4.9 out of 5 average rating, 48 reviewsCasaNova Modern City Living

Home in Chicago
4.84 out of 5 average rating, 75 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!

Home in Westmont
4.81 out of 5 average rating, 31 reviewsCozy 5-bedroom with lake views and spacious deck

Home in Des Plaines
4.79 out of 5 average rating, 186 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 apartment rentals

Apartment in Chicago
4.71 out of 5 average rating, 208 reviewsStudio flat in the heart of Chicago's Gold Coast

Apartment in Chicago
4.89 out of 5 average rating, 153 reviewsMARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Apartment in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio

Apartment in Burbank
New place to stayIconic Style, Charming Lake View

Apartment in Chicago
4.87 out of 5 average rating, 15 reviewsHUGE Modern, w/ Home Office, Chef's Kitchen, Patio

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
4.86 out of 5 average rating, 87 reviewsRiver North Hideaway w/Amazing Views and Parking
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Chicago Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Waterfront rentals Illinois
- Rentals with a hot tub Downtown Chicago
- Family-friendly rentals Downtown Chicago
- House rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Townhouse rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Hotel rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with lake access Downtown Chicago
- Flat rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Waterfront rentals Cook County
- Waterfront rentals Milwaukee
- 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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- Things to do Illinois
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- Art and culture Illinois
- Food and drink Illinois
- Things to do Cook County
- Entertainment Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Food and drink Cook County
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Food and drink Downtown Chicago
- Sightseeing Downtown Chicago