
Waterfront vacation rentals in North Side
Find and book unique waterfront accommodations on Airbnb
Top-rated waterfront accommodations in North Side
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Popular amenities for North Side 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

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
The place was great! Looked just like the photos, great space and close to transit. Everything was clean. Washer and dryer in unit was also great!

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

COZY unit near Michigan Lake 2nd floor/no elevator
Loved my stay! There was a little bit of confusion when it came to checking in and they responded to me almost immediately—which I was so grateful for after a long day of traveling. The amenities were great (me and that Keurig got along like a house on fire) and the apartment was, as described, cozy. It was perfect for me as someone who was traveling solo. After I checked out, they saw that I’d accidentally left my glasses behind and reached out to me to make sure I could grab them. Just a stellar experience from start to finish. Will definitely try to stay here again if the opportunity arises!
Waterfront house rentals

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.

Lakehouse Getaway
I love the place. it was great ti find coffee! I like sugar so I bought some and left it for the next guess. The place is super quite, clean, loved it. sure would be even more beautiful during summer. the fure place it's beautiful 😍 I enjoyed watching the deer, birds and swans and ducks. love it. ❤️

The Oak @ The Oaks On The Fox
Heidi’s place is absolutely beautiful! 🤩 It was the perfect place to relax while we were in town for appointments. The view of the river is peaceful and tranquil. The place is new, clean and thoughtfully equipped to make your stay as comfortable and enjoyable as possible. Heidi was a great host. She was quick to respond, flexible and good with communication. Thanks for a great stay!

Lakefront,Gazebo,P.Boat:40%AirB&B Fee Reimb
A very comfortable lake house! Fantastic view and access to the lake. Fully furnished kitchen makes cooking any meal as easy as at home. Plenty of space for guests to spread out. Host is responsive and accommodating.

White Turtle on Fox River welcomes you!
This was a beautiful home! Everything was super clean and felt like home. The kitchen is fully stocked and they have clean linens and blankets in case you need them. They were so kind and even included a champagne bottle as a gift! Great place to stay, highly recommend! Vladyslav was extremely helpful, responsive, accommodating and kind.

ON RIVER Barrington Home + Deck & Views
Beautiful home, has everything you need and very comfortable. There are great views of the river off of the deck. The home was well equipped with everything we needed. My husband and son especially enjoyed the Golden Tee machine in the office. While my kids aren’t young, the house comes with many amenities for young children. I would definitely recommend, we had a great stay!
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
William, Adam and I really enjoyed our stay. Your home is beautiful, charming and comfortable. The location is fabulous. Andersonville as always never disappoints. We had a great a great meal at Tala House, which was a new restaurant for us. Highly recommend your home! Thanks, The Evans
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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
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Museum of Science and Industry
- Wicker Park
- Willis Tower
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Promontory Point
- Things to do North Side
- Art and culture North Side
- Food and drink North Side
- Wellness North Side
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