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
4.82 out of 5 average rating, 87 reviewsCozy 1 BR Apartment in South Loop
18–25 Jul
Flat in Evanston
4.86 out of 5 average rating, 29 reviewsModern|Spacious|New Renovation|1BR|Evanston
18–25 Jun
Flat in Chicago
4.86 out of 5 average rating, 29 reviewsElegant 2-bed/2-bath in the heart of Uptown
18–25 Nov
Flat in Chicago
4.96 out of 5 average rating, 49 reviewsLoyola & Lake -3br/2bth close to the Lake & Loyola
21–28 Apr
Flat in Lisle
4.65 out of 5 average rating, 78 reviewsTranquility and comfort in private condo
11–18 Aug
Flat in Chicago
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
9–16 Sep
Flat in Evanston
4.78 out of 5 average rating, 127 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
25 Sep – 2 Oct
Flat in Chicago
4.78 out of 5 average rating, 9 reviewsNVCLL Chicago
29 Dec – 5 Jan
Waterfront house rentals
Home in Chicago
5.0 out of 5 average rating, 53 reviewsNEW! Lake & Skyline View on Kenwood Culdesac!
19–26 Sep
Home in Chicago
4.88 out of 5 average rating, 32 reviews'22 CasaNova Modern City Living
13–20 Aug
Home in Chicago
4.82 out of 5 average rating, 61 reviewsLake Home-3 blocks to beach/harbor 10 min 2 Loop!
26 Sep – 3 Oct
Home in Chicago
4.74 out of 5 average rating, 23 reviewsBeautiful 3 Bedroom TownHome in Rogers Park
28 Dec – 4 Jan
Home in Chicago
4.67 out of 5 average rating, 9 reviewsCozy home w/ 4 bedrooms in Bridgeport Chicago
15–22 Sep
Home in Westmont
4.89 out of 5 average rating, 18 reviewsCozy 5-bedroom with lake views and spacious deck
7–14 Nov
Home in Prospect Heights
4.93 out of 5 average rating, 44 reviewsClassy Lakefront Home w/ Charcoal Grill & Deck!
10–17 Mar
Home in Lisle
4.72 out of 5 average rating, 36 reviewsBeautiful and secluded 3 bedroom ranch style home
6–13 Apr
Waterfront apartment rentals
Apartment in Chicago
4.9 out of 5 average rating, 20 reviewsBronzeville Tribe Palace Loft
28 Dec – 4 Jan
Apartment in Chicago
4.67 out of 5 average rating, 170 reviewsStudio flat in the heart of Chicago's Gold Coast
3–10 Aug
Apartment in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
3–10 Nov
Apartment in Chicago
4.89 out of 5 average rating, 9 reviewsCozy Studio 1BR Apt near the lake on the Northside
3–10 Sep
Apartment in Chicago
4.75 out of 5 average rating, 12 reviewsSpacious Wicker Park Hideaway with Parking!
6–13 Mar
Apartment in Chicago
5.0 out of 5 average rating, 49 reviewsWhere you want to BE! Stylish, Comfy, Luxe
12–19 Mar
Apartment in Chicago
4.8 out of 5 average rating, 10 reviewsLovely 1 Bedroom with Fireplace and Home Office
10–17 Jul
Apartment in Calumet City
4.89 out of 5 average rating, 9 reviewsChicago/Grant Park/Solider Field
4–11 Apr
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Chicago
- Rentals with pools Downtown Chicago
- Rentals with a patio Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Loft rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Beachfront rentals Downtown Chicago
- House rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a cinema 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