
Waterfront vacation rentals in Near North Side, Chicago
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Top-rated waterfront accommodations in Near North Side, Chicago
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Popular amenities for Near North Side, Chicago waterfront rentals
Waterfront apartment rentals

Sheridan Beach Apartment
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! 🤍

The Wine Down
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

3BR Luxury Modern Apartment
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.

Cozy Chicago Apartment next to the River
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!

Cozy 1BR in South Loop | Convenience in the City
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.

Elegant 2-bed/2-bath in the heart of Uptown
We chose Seun's place over others because of the off the street garage. However, the whole stay was enjoyable and comfortable. The place doesn't have the extra amenities we have gotten used to, like for example bottled water, first breakfast goodies (cereal bars, coffee) or snacks, other than whatever was left by prior guests. that was the only thing we missed.

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

3 Bed 3 Bath Lakefront Oasis, Parking Included
I would stay again
Waterfront house rentals

Lakefront Prospect Heights Home: Ice Fish On-Site
The place was perfect for our needs in Chicago. It’s well kept, up to date, and fits the description.

Sprawling private fenced home with pond view!
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.

CasaNova Modern City Living
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!!

Lakefront View Getaway Home! Hot tub! Kayak!
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.

Spacious house patio/free parking
Accurate photos of the place, everything felt very new. Responsive host.

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!
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 🍾 😀 😄 ❤️

Cozy 5-bedroom with lake views and spacious deck
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.

NEW! Lake & Skyline View on Kenwood Culdesac!
Awesome 4 level home. All five of our travel group had a comfortable bed. The Master bedroom/bath AND outside seating area was beautiful, spacious and well decorated. We all enjoyed taking turns in the walk in shower with the spa jets and wished we had more time to enjoy the large tub with a TV mounted over it! The view of the water and outdoor seating options were wonderful for us to gather and talk. Would highly recommend and I would definitely return!
Waterfront condo rentals

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Gorgeous, spacious, updated condo in the perfect location. Incredible lake views from the kitchen window. Hosts were very responsive and friendly. Highly recommend!

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

Where you want to BE! Stylish, Comfy, Luxe
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!

Spacious Wicker Park Hideaway with Parking!
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.

River North Hideaway w/Amazing Views and Parking
We loved everything about this place, especially the location. Walkable to everything! The condo was lovely, perfect for our family to stay.

Bronzeville Tribe Palace Loft
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!

Breathtaking water view condo
Great balcony space to bring in a lot of sunlight and to check out the sunset. Lots of counter space to work with to cook meals. Primary and second bedrooms with their OWN balconies to take in the views as well. Only thing is you definitely need a car to do anything nearby, but that's not Elleni's issue. Everything that she could control was excellent!

Elegant Hideaway in the Heart of Andersonville
We enjoyed our long weekend at William's place in Andersonville. It is beautifully decorated, very comfortable and super clean. It was nice having so many great restaurants and shops right down the block. The kitchen is well stocked if you want to cook. Would definitely stay here again!
Quick stats about waterfront rentals in Near North Side, Chicago
Total rentals
30 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Pet-friendly rentals Near North Side
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Wicker Park
- Lincoln Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Brookfield Zoo
- Flossmoor Golf Club
- Illinois Beach State Park
- Garfield Park Conservatory
- Skokie Country Club
- Chicago Cultural Center