Waterfront holiday rentals in Downtown Chicago

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Downtown Chicago

Waterfront apartment rentals

Guest favourite
Flat in Chicago
5 out of 5 average rating, 9 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

ShyamRating, 5 stars1 week ago
Loved our stay here. a gorgeous home with a ton of space and top notch finishes. Nestled between Lincoln Park and Boystown, this place was the perfect home base for our group.
Guest favourite
Flat in Chicago
4.94 out of 5 average rating, 32 reviews

Sheridan Beach Apartment

SierraRating, 5 stars1 month ago
This property is beautiful and cozy, and it's within walking distance to many attractions. The beach and coffee shops are just a couple of examples. Our host, Amy, provided excellent hospitality; she is very informative, friendly, and checked in periodically to ensure our stay was as comfortable as possible. I would definitely come back to this place again! 🤍
Superhost
Flat in Chicago
4.75 out of 5 average rating, 8 reviews

The Wine Down

LeeshawnRating, 5 stars3 days ago
Great apartment well decorated and felt at home,super comfortable couch and beds,I would book this spot every time when I’m in Chicago,also accommodated us for the WiFi going down which was superb
Guest favourite
Flat in Chicago
4.86 out of 5 average rating, 22 reviews

3BR Luxury Modern Apartment

AdamRating, 5 stars1 month ago
My family and I absolutely loved the apartment. It is clean, modern, spacious and comfortable. The gym is just across the hall from the apartment, which was super convenient for us. The lounge area next to the apartment is also a huge plus for getting some work done. You also get a nice view of the city from the unit and from the gym and lounge area. The building is conveniently located on the north end of River North, walking distance to restaurants, public transport & shops. Despite it's somewhat central location, the unit is quiet inside. Lastly, communication with the host was top notch. Check in & check out process were a breeze. I highly recommend this apartment.
Top guest favourite
Flat in Chicago
4.98 out of 5 average rating, 46 reviews

Cozy Chicago Apartment next to the River

GrantRating, 5 stars1 month ago
We thouroughly enjoyed our stay in this cozy home during our visit to Chicago for St Patrick Day weekend! Additionally, it it really close to everything you would want to see downtown. Albert and Monica were great hosts and easy to communicate with and provided some great recommendations. Would defentily recommend to anyone looking for a place to stay during your trip to Chicago!
Flat in Chicago
4.81 out of 5 average rating, 26 reviews

2b2b in River North

SyedRating, 5 stars2 weeks ago
Had a great stay here. Host was helpful with any questions we had. Place was clean and as described
Flat in Chicago
4.72 out of 5 average rating, 126 reviews

Cozy 1BR in South Loop | Convenience in the City

DavidRating, 5 stars1 month ago
Great place to stay! Can get anywhere in the city, its right off the "L". Not far from Michigan Ave, either. Would highly recommend this place to anyone who is traveling to Chicago.
Superhost
Flat in Chicago
4.86 out of 5 average rating, 70 reviews

Elegant 2-bed/2-bath in the heart of Uptown

SusanRating, 5 stars2 weeks ago
The unit was wonderful and made our last minute trip to catch the Cubs home opener worth it! Couple of blocks from the red line and down the street from the Uptown Deli, which has fabulous sandwiches and desserts. Would recommend this location to anyone!

Waterfront house rentals

Home in Prospect Heights
4.91 out of 5 average rating, 53 reviews

Lakefront Prospect Heights Home: Ice Fish On-Site

AllenRating, 5 stars2 months ago
The place was perfect for our needs in Chicago. It’s well kept, up to date, and fits the description.
Guest favourite
Home in Schaumburg
4.91 out of 5 average rating, 54 reviews

Sprawling private fenced home with pond view!

KadijahRating, 5 stars4 months ago
Highly recommend this Airbnb. The owner has truly made it a home away from home. She has everything you need in the kitchen, plentiful pillows, extra towels and blankets. The house is very private as it is at the end of a cul de sac in a quaint neighborhood. There is a walking trail and field directly behind the house where you see families and people with their dogs. Though very tranquil, the house is very close to stores and restaurants. It was very clean and rivaled most hotels in that regard. The beds were comfortable and the showers were perfect. Nice that it had two sitting areas and TVs in every room! The most amazing thing about her property is Stephanie herself. She takes great pride and was always readily available. I felt like I had a friend while away from home. She helped with whatever she could.
Guest favourite
Home in Chicago
4.88 out of 5 average rating, 49 reviews

CasaNova Modern City Living

KatieRating, 5 stars6 months ago
Lilly was prompt in her responses and very helpful. The place was well kept and clean. A quick Uber ride to downtown. Our group really enjoyed our stay!!
Guest favourite
Home in Downers Grove
4.97 out of 5 average rating, 33 reviews

Lakefront Getaway Home! Amazing View! Hot tub! Ski

VincentRating, 5 stars2 days ago
We had a fantastic weekend at Hugo's place! It was extremely spacious and well-equipped for large groups of people, with many extras in addition to those listed in the description. Hugo was extremely responsive and accommodating. The price is well worth it for groups of 10+ people, and we would happily stay there again.
Superhost
Home in Chicago
5 out of 5 average rating, 3 reviews

Spacious house patio/free parking

NatthaRating, 5 stars1 month ago
Accurate photos of the place, everything felt very new. Responsive host.
Guest favourite
Home in Chicago
4.84 out of 5 average rating, 76 reviews

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

DarlaRating, 5 stars1 month ago
This place was amazing... They layout was terrific. quiet neighborhood, safe, and had everything we needed. we were celebrating my birthday (pre) My friends 🧡 Even set up a Bday table for me down stairs and we had our in vip golden girlz(ladies) celebrations 🍾 😀 😄 ❤️
Home in Des Plaines
4.69 out of 5 average rating, 35 reviews

House 1 minute from O'hare Airport

GabrielRating, 5 stars3 months ago
I was enjoy this house with my family and we had a good time there! The house has everything you need and the location is nearby airport!
Home in Westmont
4.78 out of 5 average rating, 32 reviews

Cozy 5-bedroom with lake views and spacious deck

AmandaRating, 5 stars4 months ago
The house amenities were well thought out and had everything we would find and need in our our home. extra linens, convenient and safe location, and even toys and pack and plays for the kids. would absolutely recommend for any and everyone.

Waterfront apartment rentals

Superhost
Apartment in Chicago
4.83 out of 5 average rating, 23 reviews

West Town Hideaway Sleeps 18 + Parking!

DeniceRating, 5 stars3 months ago
Stayed here for family holiday in Chicago! West Town was the perfect location for us, close to transportation, very walkable, lots of coffee shops and places to eat! We used both units for our family and found them both to be exactly as described. The house was in a very quiet neighborhood and came with 2 parking spaces! We loved the indoor access so we could go between both units. The living space in bottom unit was big enough for us all to be together. Plenty of bedrooms and bathrooms. Beds were comfortable and rooms were clean. The kitchen had lots of dishes but could use a few more pots and pans ( was a little difficult to heat our holiday dinner)- but with so many great places to eat- most people probably eat out anyway! William was a great host, he responded quickly to questions and had a slight problem fixed within 2 hours of us contacting him. We are so glad we had such a great place to spend the holidays! Highly recommend!
Superhost
Apartment in Chicago
4.89 out of 5 average rating, 158 reviews

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

MargaretRating, 5 stars1 month ago
Gorgeous, spacious, updated condo in the perfect location. Incredible lake views from the kitchen window. Hosts were very responsive and friendly. Highly recommend!
Guest favourite
Apartment in Chicago
4.87 out of 5 average rating, 15 reviews

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

SaraRating, 5 stars6 months ago
Cannot speak highly enough of this space! It was HUGE! Beautiful and very convenient! The Red line and Green Line train stations are both within easy walking distance. From either we could get to anywhere we wanted to go with transfers. The Hosts were responsive and flexible with an early check in(with a fee) and understanding when we woke up late and checked out 20 minutes late. They had several recommendations for places to eat, see and things to do. Hope to be back!
Guest favourite
Apartment in Chicago
5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

EdwardRating, 5 stars6 months ago
This has to be the best AirBnB we have stayed at. The apartment was like home from home, super clean and exceeded our expectations. The location of the apartment is a short walk from the L, has everything you need within a 5 minute walk and is in a great neighbourhood. John, the host, is outstanding. Nothing is too much trouble and he gives some great recommendations of local restaurants/ activities. I would highly recommend this apartment if you are in Chicago - we are sure to be back!
Superhost
Apartment in Chicago
4.78 out of 5 average rating, 23 reviews

Spacious Wicker Park Hideaway with Parking!

NicoleRating, 5 stars1 week ago
This place is near so many spots it was awesome! to go down and get food right below or just walking across the street and grabbing some food. the place was very well cleaned, had great spots just to sit and chill. beds very comfortable, rooms very spacious. water pressure can be very in and out sometimes but water was warm/hot and lasted a full shower.
Superhost
Apartment in Chicago
4.86 out of 5 average rating, 95 reviews

River North Hideaway w/Amazing Views and Parking

AimeeRating, 5 stars1 week ago
We loved everything about this place, especially the location. Walkable to everything! The condo was lovely, perfect for our family to stay.
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 36 reviews

Bronzeville Tribe Palace Loft

KeairaRating, 5 stars7 months ago
Beautiful building and a beautiful space! My family and I really enjoyed our stay. We had more than enough space and everyone was comfortable. Richard was very accommodating we would definitely stay again!
Superhost
Apartment in Lombard
4.83 out of 5 average rating, 12 reviews

Breathtaking water view condo

SteveRating, 5 stars3 days ago
Elleni was a great host. Very responsive to our texts. The unit was very nice and clean. Had everything we needed for our overnight stay. I agree with a previous guest to not let the dated outside or elevator stop you from staying here as the unit was very nice!

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