
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

Sheridan Beach Apartment

The Wine Down

Cozy Chicago Apartment next to the River

Cozy 1BR in South Loop | Convenience in the City

New renovation|1BR|Stylish|Modern|Next to the Lake

âď¸âď¸Entire Unite 2-Bdr. HORNER PARKâď¸âď¸

3 Bed 3 Bath Lakefront Retreat, Parking Included

COZY unit near Michigan Lake 2nd floor/no elevator
Waterfront house rentals

Renovated space in a historic row house.

Gem Near Hyde Park/McCormick Place/Beach

Bike & Kayak: Lakefront Prospect Heights Home

Sunny,Comfortable,CleanTop Location at Lake,Beach

Lakefront View Getaway Home! Hot tub! Kayak!

Comfortable private room near Lake and transit.

Historic Manor House Private Room #1 in Evanston

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!
Waterfront apartment rentals

Modern Wrigley Oasis with Parking!

Iconic Style, Charming Lake View

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

HUGE Modern, 1BD Home Office, Chef's Kitchen Patio

Where you want to BE! Stylish, Comfy, Luxe

Spacious Wicker Park Hideaway with Parking!

Bronzeville Tribe Palace Loft

Elegant Hideaway in the Heart of Andersonville
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Pet-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Loft rentals Downtown Chicago
- House rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Waterfront rentals Cook County
- Waterfront rentals Illinois
- Waterfront rentals United States
- 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
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Food and drink Downtown Chicago
- Sightseeing Downtown Chicago
- Tours Downtown Chicago
- Things to do Cook County
- Tours Cook County
- Food and drink Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Things to do Illinois
- Art and culture Illinois
- Tours Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Nature and outdoors Illinois
- Things to do United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Sightseeing United States
- Entertainment United States
- Tours United States
- Wellness United States
- Art and culture United States