
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

3BR Luxury Modern Apartment

Cozy Chicago Apartment next to the River

Cozy 1BR in South Loop | Convenience in the City

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Modern Lakefront Oasis with Breathtaking Views!

Loyola & Lake -3br/2bth close to the Lake & Loyola

Spacious & Elegant N Side Apt Near Beach & Transit
Waterfront house rentals

Beautiful space in historic house near lakefront.

Bike & Kayak: Lakefront Prospect Heights Home

CasaNova Modern City Living

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!

Studio flat in the heart of Chicago's Gold Coast

Iconic Style, Charming Lake View

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

Where you want to BE! Stylish, Comfy, Luxe

Spacious Wicker Park Hideaway with Parking!

River North Hideaway w/Amazing Views and Parking

Bronzeville Tribe Palace Loft
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Rentals with breakfast Downtown Chicago
- Rentals with a patio Downtown Chicago
- Apartment rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Flat rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- House rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with pools Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Waterfront rentals Cook County
- Waterfront rentals Illinois
- Waterfront rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Nature and outdoors Downtown Chicago
- Food and drink Downtown Chicago
- Sightseeing Downtown Chicago
- Sports activities Downtown Chicago
- Tours Downtown Chicago
- Things to do Cook County
- Food and drink Cook County
- Art and culture Cook County
- Tours Cook County
- Sightseeing Cook County
- Sports activities Cook County
- Things to do Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Sports activities Illinois
- Tours Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Things to do United States
- Sightseeing United States
- Art and culture United States
- Wellness United States
- Entertainment United States
- Sports activities United States
- Tours United States
- Food and drink United States
- Nature and outdoors United States