Waterfront vacation rentals in Downtown Chicago

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Popular amenities for Downtown Chicago waterfront rentals

Waterfront apartment rentals

Guest favorite
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 favorite
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 starstoday
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 favorite
Apartment 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 favorite
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!

Waterfront house rentals

Guest favorite
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 favorite
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 favorite
Home in Downers Grove
4.97 out of 5 average rating, 32 reviews

Lakefront Getaway Home! Amazing View! Hot tub! Ski

GraemeRating, 5 stars6 days ago
We had a wonderful stay. I couldn’t believe there was a little boat for the kids to use and even life jackets!! You couldn’t ask for a better location or more responsive host! We especially appreciated that there was a bedroom on the main level for an elderly guest.
Top guest favorite
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 stars4 weeks ago
Accurate photos of the place, everything felt very new. Responsive host.
Guest favorite
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 rentals

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 favorite
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 favorite
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, 94 reviews

River North Hideaway w/Amazing Views and Parking

ScottRating, 5 stars2 weeks ago
We had a fantastic experience staying at this apartment! The host was excellent, and the place was exactly as advertised—spacious, clean, and well-maintained. The location is perfect, with Michigan Avenue just a 5-minute walk away and the Riverwalk only 10 minutes on foot. Check-in was seamless, and the host was always prompt and clear in communication. The only potential consideration for those with mobility challenges is the stairs. The apartment is on the third floor, and the stairs are a bit steep and narrow. Overall, it was a great stay, and I can’t wait to return!
Guest favorite
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
4.82 out of 5 average rating, 11 reviews

Breathtaking water view condo

AshleyRating, 5 stars3 weeks ago
Great stay, Ellen was a great host that was very responsive and had everything ready. Very good location and place
Superhost
Condo in Chicago
4.85 out of 5 average rating, 47 reviews

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

ScottRating, 5 stars1 month ago
Can't say enough to describe how much I and my team enjoyed our stay. We were in town for a convention at McCormick and wanted a place that we could all stay together for "team building" opportunities. Plus...it sure beats sitting in a hotel room separately. The place was fantastic. Each member of my team had their own bedroom and bathroom. Beautiful kitchen, unbelievable view of Lake Michigan, plenty of space in the living area to hang out. The instructions for access - which can be tricky in Chicago with the necessary enhanced security requirements - were clearly laid out with description and pictures which made it easy on us. And in case you missed it...these are two separate units on the same floor. You're the ONLY people on the 10th floor. So it was extremely convenient for two of my team members to "visit" with us and then retreat to their own space whenever they chose. I would definitely stay here again.

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