Waterfront vacation rentals in North Side

Find and book unique waterfront rentals on Airbnb

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Popular amenities for North Side waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Chicago
5 out of 5 average rating, 10 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

ChristianRating, 5 stars1 week ago
Daniel’s place in Lincoln Park was spectacular. The location is prime. The accommodations were perfect for my large family. Easily walkable. He was a great host.
Guest favorite
Apartment in Chicago
4.94 out of 5 average rating, 33 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
4.67 out of 5 average rating, 9 reviews

The Wine Down

LeeshawnRating, 5 stars1 week 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 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
4.72 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, 71 reviews

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

SusanaRating, 5 stars2 weeks ago
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.
Guest favorite
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!
Apartment in Chicago
4.52 out of 5 average rating, 48 reviews

HUGE & BRAND NEW BEACH Apartment is Ready For You!

KrisRating, 5 stars7 months ago
Liz’s Airbnb was a perfect base of operations for me and my husband. The space was roomy and comfortable. We were gone lots for events around a family member’s birthday, but also enjoyed our time at and around the Airbnb. We especially enjoyed Loyola Beach, a short walk from Liz’s place. Lake Michigan water temps were lovely.

Waterfront house rentals

Guest favorite
Private room in Chicago
4.87 out of 5 average rating, 132 reviews

Renovated space in a historic row house.

MargaretRating, 5 stars2 weeks 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 Schaumburg
4.91 out of 5 average rating, 54 reviews

Sprawling private fenced home with pond view!

KadijahRating, 5 stars4 months ago
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.
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, 34 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

VincentRating, 5 stars1 week ago
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.
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 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
4.7 out of 5 average rating, 225 reviews

Studio flat in the heart of Chicago's Gold Coast

JeremyRating, 5 stars1 week ago
The Price was PERFECT for this beautiful location of GOLD COAST!!
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
4.78 out of 5 average rating, 23 reviews

Spacious Wicker Park Hideaway with Parking!

NicoleRating, 5 stars1 week ago
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.
Superhost
Condo in Chicago
4.86 out of 5 average rating, 95 reviews

River North Hideaway w/Amazing Views and Parking

AimeeRating, 5 stars2 weeks ago
We loved everything about this place, especially the location. Walkable to everything! The condo was lovely, perfect for our family to stay.
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
4.86 out of 5 average rating, 14 reviews

Breathtaking water view condo

SteveRating, 5 stars1 week 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!
Guest favorite
Condo in Chicago
4.95 out of 5 average rating, 100 reviews

Elegant Hideaway in the Heart of Andersonville

NatalieRating, 5 stars4 weeks ago
Our family had a great stay at William's place. The condo was super clean, inviting, quiet, and comfortable. We appreciated the high quality appliances and linens, as well as the thoughtful details, such as umbrellas to use. The location is excellent. It is very easy to walk to many restaurants and shops and the lake is close by. The area gets busy at night an on the weekends, but we had no trouble finding parking during our visit. For some reason the keypad did not work when we arrived. We messaged William and he responded immediately. He had a back up option for us and we were able to enter the condo within minutes. I highly recommend booking this condo if you are coming to Chicago and want to explore all Andersonville has to offer!

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