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

Apartment in Chicago
5 out of 5 average rating, 4 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

LaurenRating, 5 stars1 month ago
This rental exceeded our expectations! Daniel was very responsive, and provided clear, helpful instructions. The home was impeccably clean and beautifully renovated, offering upscale finishes, a beautiful kitchen, and a spacious deck perfect for relaxing (although it was too cold when we visited). The location is unbeatable, with easy access to the lake, numerous dining options, Lincoln Park Zoo, and much more. The vibrant neighborhood combines old Chicago architectural charm with serene green spaces, making it ideal for any Chicago getaway. After staying here once, I'd definitely seek it out again for my next visit.
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 30 reviews

Sheridan Beach Apartment

BradleyRating, 5 stars3 months ago
Our host responded in seconds with any questions we had! We removed our shoes at the door and our socked feet proved how clean this place is. Super well stocked bathroom and clean comfortable bed. Very quiet location yet less than 2 blocks from the L, restaurants, beach and just steps away from the bus and market. Some evidence of homelessness on Sheridan Rd. and in the park at the beach. We were only approached 1 time in 3 days. Street lighting was abundant especially the ally access. We wouldn’t hesitate to use this location for a return trip.
Apartment in Chicago
5 out of 5 average rating, 4 reviews

The Wine Down

ShannonRating, 5 stars3 weeks ago
I was aware of the area prior to our stay. This home offered many things to my family It is cold in chicago and providing extra blankets came in handy. The home is beautifully decorated. You have comfortable seating, comfortable beds. All of the decor and finishes made me feel at home. The egg chair. my favorite! As well as all of the additional security that really did bring peace of mind. Thank you for allowing is to stay in your home.
Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 43 reviews

Cozy Chicago Apartment next to the River

ElizabethRating, 5 stars1 month ago
Albert and Monica were great hosts!! The Airbnb location is perfect for people visiting Chicago. It’s close to a lot of activities we did and the uber ride is affordable too. Overall, we enjoyed our stay!
Guest favourite
Apartment in Chicago
5 out of 5 average rating, 19 reviews

3BR Luxury Modern Apartment

TimothyRating, 5 stars1 month ago
We had a great stay over NYE. Very cool area of Chicago and well secured especially with phone capability. Do wish we had TV’s in the rooms but due to short stay and it being NYE, no issue. Also, the oldest bar in Chicago is only blocks away so make sure you check that out . Overall, great stay
Superhost
Apartment in Chicago
4.77 out of 5 average rating, 22 reviews

2b2b by Water Tower and the Lake

CarlosRating, 5 stars1 month ago
The apartment is spacious, has everything you need and the location is unbeatable. An excellent option in Chicago
Superhost
Apartment in Chicago
4.86 out of 5 average rating, 65 reviews

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

LauraRating, 5 stars1 month ago
Seun’s place had everything we needed for a couple nights. It was clean and comfortable. The kitchen had everything we needed to use, even a blender! It is on the basement level of the condos but still had decent light come through and there was enough lights to lite his place during the night time. The parking garage attached to the condos was a great advantage of this place and was very convenient. The only thing I would recommend is going through the front entrance and going into the condo to retrieve the garage opener and gate key. Then getting back in the car and going to the back entrance where u can get in through the garage now that you have opener. The gates by garage are locked so you need a key to get through the gates and that’s inside the condo as well. Overall, it’s just what we needed for a couple nights! Thanks Seun for sharing your lovely place.
Guest favourite
Apartment in Evanston
4.93 out of 5 average rating, 80 reviews

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

AdwoaRating, 5 stars1 week ago
The place is great and Alex’s got as shown. They really went out their way to get us some space heaters during our stay cause we were too cold in the unit. Thank you!

Waterfront house rentals

Guest favourite
Private room in Chicago
4.87 out of 5 average rating, 129 reviews

Renovated space in a historic row house.

MargaretRating, 5 stars1 month ago
Our daughter and son-in-law live VERY nearby, and having innumerable times walked past the historic row of houses in which this apartment is located, we jumped at the chance to stay here. This was not only a perfect location for us, but was just the right size. Having an entire library of very interesting books added a lot to our enjoyment. The shower was terrific. The bed was very comfy, too. This was a great place to stay during Christmas week!
Home in Prospect Heights
4.91 out of 5 average rating, 53 reviews

Lakefront Prospect Heights Home: Ice Fish On-Site

AllenRating, 5 stars2 weeks 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
4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

KatieRating, 5 stars4 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 Chicago
4.84 out of 5 average rating, 75 reviews

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

HeejooRating, 5 stars2 months ago
It has huge spaces for big family. We enjoyed three nights in Chicago. Rooms on second floor were good for sleeping with good heating but rooms on lower levels were not.
Home in Des Plaines
4.69 out of 5 average rating, 35 reviews

House 1 minute from O'hare Airport

GabrielRating, 5 stars1 month 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
4.81 out of 5 average rating, 31 reviews

Cozy 5-bedroom with lake views and spacious deck

AmandaRating, 5 stars2 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.
Home in Des Plaines
4.79 out of 5 average rating, 186 reviews

Exotic House - Few minutes from O'Hare and Chicago

YvetteRating, 5 stars2 months ago
We had a wonderful time and we were so comfortable in the house. We felt like we were at home. Just a few minor cosmetic issues with the home like broken mini blinds and broken window screens but this did not impact our wonderful experience. The neighborhood was perfect - very close to highway, activities in Des Plaines and Rosemont are very close by. We would highly recommend this beautiful home.
Home in Chicago
4.61 out of 5 average rating, 36 reviews

Beautiful 3 Bedroom TownHome in Rogers Park

FlorenciaRating, 5 stars5 months ago
The place was perfect for our group of six. The host was always very communicative and responsive. 15 min walk to the train station and there is plenty of restaurants and around the area.

Waterfront condo accommodation

Superhost
Condo in Chicago
4.89 out of 5 average rating, 153 reviews

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

PaulRating, 5 stars3 weeks ago
The place was last as described and as the pictures showed. Wendy and Matt were easy to communicate with and accommodating
Superhost
Condo in Chicago
4.8 out of 5 average rating, 25 reviews

Lovely condo studio

EileenRating, 5 stars6 months ago
Great studio apartment with very friendly neighbors in a great neighborhood with amazing restaurants. Walking distance to Andersonville, a neighborhood with antique book stores, oddity shops, enough to keep you busy all day. Perfect location. I will stay there again.
Guest favourite
Condo in Chicago
4.87 out of 5 average rating, 15 reviews

HUGE Modern, w/ Home Office, Chef's Kitchen, Patio

SaraRating, 5 stars4 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 stars4 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
4.79 out of 5 average rating, 19 reviews

Spacious Wicker Park Hideaway with Parking!

AnnieRating, 5 stars6 months ago
This was so roomy. We had our grandkids with us and we felt very comfortable. So many food choices nearby. We had a wonderful visit in Chicago!
Superhost
Condo in Chicago
4.85 out of 5 average rating, 89 reviews

River North Hideaway w/Amazing Views and Parking

LindseyRating, 5 stars1 month ago
My friends and I had a great time at William's place. Check-in directions were easy, and William was very responsive to any questions I had upon arrival. The place was beautiful and very clean. It had great city views from the living area, a fully equipped kitchen, lots of closet space, and spacious bedrooms. The location is also great, about a 2 minute walk to Michigan Ave. I would recommend William's place to everyone!
Guest favourite
Condo in Chicago
4.83 out of 5 average rating, 36 reviews

Bronzeville Tribe Palace Loft

KeairaRating, 5 stars5 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 Chicago
4.84 out of 5 average rating, 45 reviews

MAG MILE MEGA Entire Floor 4BD/4BA (+Roof/Gym)

RachelRating, 5 stars1 month ago
My family and I had the best time staying here. The location was perfect with stunning views of Lake Michigan and walkable to so many restaurants, coffee shops and spots for shopping. Thank you Wendy and Matt for hosting us and being so helpful leading up to and throughout our stay!

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