Waterfront holiday rentals in Downtown Chicago

Find and book unique waterfront accommodation on Airbnb

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Popular amenities for Downtown Chicago waterfront rentals

Waterfront apartment accommodation

Guest favourite
Apartment in Chicago
5 out of 5 average rating, 8 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

JessicaRating, 5 stars3 weeks ago
Daniel and Tatyana's place was wonderful for our four person stay. We had ample room, were able to do a load of laundry and hung out in the main living area catching up. While we didn't cook, we made ourselves coffee and tea and both were easy to do. There are plenty of restaurants nearby and we sampled many of them. We spent time on the outdoor porch which was lovely for the duration of our visit. The hosts were friendly, responsive and respectful. They clearly communicated and made sure we felt comfortable. Would definitely stay here again with friends or family.
Guest favourite
Apartment 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
Apartment in Chicago
4.75 out of 5 average rating, 8 reviews

The Wine Down

LeeshawnRating, 5 stars1 day 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
Top Guest favourite
Apartment 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!
Apartment 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
Apartment 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
Apartment 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!
Guest favourite
Apartment in Evanston
4.92 out of 5 average rating, 84 reviews

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

GabbyRating, 5 stars1 month ago
This stay in Evanston was so convenient! It was a 15 minute walk from the Purple line, which made it easy to get to the city. The beach was also beautiful and it was only a 2 minute walk!

Waterfront house rentals

Guest favourite
Private room in Chicago
4.87 out of 5 average rating, 131 reviews

Renovated space in a historic row house.

MargaretRating, 5 stars1 week ago
We booked this room for my sister who was visiting family with us. Having stayed here ourselves before over the holidays, we knew it was just the right thing for her. She was very comfortable and slept well.
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 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 starstoday
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.
Top Guest favourite
Private room in Chicago
4.97 out of 5 average rating, 101 reviews

Comfortable private room near Lake and transit.

FelicityRating, 5 stars4 months ago
We found our stay with Paula to be absolutely delightful and better than if we had a place all to ourselves. She was generous, responsive, and helpful in many ways. We could not have had a nicer, better hostess and we look forward to staying with her the next time we visit Chicago.
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!

Waterfront condo accommodation

Superhost
Condo 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
Condo in Chicago
4.89 out of 5 average rating, 158 reviews

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

MargaretRating, 5 stars4 weeks 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
Condo 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
Condo 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
Condo in Chicago
4.77 out of 5 average rating, 22 reviews

Spacious Wicker Park Hideaway with Parking!

ElishaRating, 5 stars1 month ago
George was a great host. When we needed to communicate with him, he was very attentive. Would recommend.
Superhost
Condo 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
Condo 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
Condo in Lombard
4.83 out of 5 average rating, 12 reviews

Breathtaking water view condo

SteveRating, 5 stars1 day 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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