Waterfront vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago waterfront rentals
Waterfront apartment rentals
Rental unit in Chicago
4.93 out of 5 average rating, 30 reviewsSheridan Beach Apartment
Rental unit in Chicago
5 out of 5 average rating, 3 reviewsLux apartment near Michigan lake
Rental unit in Chicago
4.75 out of 5 average rating, 16 reviews2b2b by Water Tower and the Lake
Rental unit in Chicago
4.79 out of 5 average rating, 33 reviewsModern Cozy Top Floor Duplex near Wrigley
Rental unit in Chicago
4.76 out of 5 average rating, 117 reviewsCozy 1 BR Apartment in South Loop
Rental unit in Chicago
4.59 out of 5 average rating, 143 reviewsBoutique Flat in Lincoln Park with Free Parking
Rental unit in Chicago
4.7 out of 5 average rating, 89 reviewsModern Lakefront Retreat with Breathtaking Views!
Rental unit in Chicago
4.54 out of 5 average rating, 46 reviewsHUGE & BRAND NEW BEACH Apartment is Ready For You!
Waterfront house rentals
Home in Chicago
5 out of 5 average rating, 6 reviewsGem Near Hyde Park/McCormick Place
Home in Prospect Heights
4.92 out of 5 average rating, 48 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 Downers Grove
4.96 out of 5 average rating, 23 reviewsLakefront Getaway Home! Lots of Fun! Win.Discount$
Home in Chicago
4.84 out of 5 average rating, 73 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
Home in Des Plaines
4.59 out of 5 average rating, 27 reviewsHouse 1 minute from O'hare Airport
Home in Westmont
4.89 out of 5 average rating, 28 reviewsCozy 5-bedroom with lake views and spacious deck
Waterfront condo rentals
Condo in Chicago
4.7 out of 5 average rating, 200 reviewsStudio flat in the heart of Chicago's Gold Coast
Condo in Chicago
4.8 out of 5 average rating, 25 reviewsLovely condo studio
Condo in Chicago
4.88 out of 5 average rating, 179 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
Condo in Chicago
4.86 out of 5 average rating, 14 reviewsLovely 1 Bedroom with Fireplace and Home Office
Condo in Chicago
5 out of 5 average rating, 55 reviewsWhere you want to BE! Stylish, Comfy, Luxe
Condo in Chicago
4.79 out of 5 average rating, 19 reviewsSpacious Wicker Park Hideaway with Parking!
Condo in Chicago
4.84 out of 5 average rating, 76 reviewsRiver North Hideaway w/Amazing Views and Parking
Condo in Chicago
4.86 out of 5 average rating, 35 reviewsBronzeville Tribe Palace Loft
Destinations to explore
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- South Side Vacation rentals
- Schaumburg Vacation rentals
- Chicago Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Rentals with a washer and dryer Downtown Chicago
- Condo rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a home theater Downtown Chicago
- House rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Apartment rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Monthly Rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Waterfront rentals Milwaukee
- Waterfront rentals Illinois
- Waterfront rentals Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses 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
- Things to do United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Art and culture United States
- Sightseeing United States
- Entertainment United States
- Wellness United States
- Things to do Illinois
- Sightseeing Illinois
- Food and drink Illinois
- Art and culture Illinois
- Things to do Cook County
- Food and drink Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Things to do Downtown Chicago
- Sightseeing Downtown Chicago
- Food and drink Downtown Chicago
- Art and culture Downtown Chicago
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes