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Beachfront vacation rentals in North Side

Find and book unique beachfront homes on Airbnb

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Popular amenities for North Side beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.
Townhouse in Chicago
4.84 out of 5 average rating, 206 reviews

Historic lux Townhouse on Chicago's Gold Coast

RobynRating, 5 stars6 days ago
The house was beautiful and in a very nice, safe neighborhood. There was some construction going on next door, but other than that, the place was everything we hoped it would be. We stayed here while we got married at a nearby venue in River North and it was able to accommodate our bridal party during our getting ready session and provide a quiet place to rest once our wedding was over.
Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in Chicago
4.9 out of 5 average rating, 175 reviews

Executive Apartment on Lake Michigan with parking

JoshuaRating, 5 stars3 days ago
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!
Guest favorite
A spacious living area features a light-colored sectional sofa and a modern glass coffee table. Decorative elements include a white fireplace and a wall-mounted television. Natural light streams through sheer curtains, illuminating the polished wooden floors throughout the room.
Apartment in Chicago
4.9 out of 5 average rating, 101 reviews

Cannabis Condo 4BR

JenniferRating, 5 stars3 weeks ago
Shomari was a great host, very friendly and gave great recommendations. We had all the towels and he had toiletry items in the bathroom and cooking items (spices, extra drinks) in the kitchen. My girls and I didn’t feel unsafe in the area, although finding street parking on the block can be tough, depending on the time of day. His place is a 25-30 min drive to downtown, soldier field and McCormick place, it can be less or more depending on the traffic. It was a great stay and I would recommend.
Guest favorite
The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.
Apartment in Chicago
4.92 out of 5 average rating, 233 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

TeriRating, 5 stars3 weeks ago
This home has everything you need, especially if you have a large group. It’s beautiful and in a great location. Very quick walk to all the great restaurants etc., but you don’t have the noise from them. Will is a great host and I would definitely stay here again.

Private beachfront home rentals

The living area features a teal sofa adorned with decorative pillows and a cozy throw. Two white accent chairs flank a large round coffee table, which is complemented by a small potted plant. Light walls and a framed artwork provide a modern aesthetic.
Apartment in Evanston
4.66 out of 5 average rating, 163 reviews

✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨

PrajaktaRating, 5 stars2 weeks ago
Demitri is a very good host, he will respond to your queries quickly. Location was nice - 603, Sheridan Rd, we could go to the lake beach which was only 2 mins walk away. Please do not bring a lot of heavy luggage as there is no elevator in the apt and this airbnb is on the 3rd floor (which is clearly mentioned in the description.) Overall amazing place to stay and enjoy the beautiful Michigan lake beach nearby!
A living area is furnished with two brown chairs facing a circular wooden coffee table. A television is mounted on a white media console beneath a scenic image. A green plant is positioned in the corner, adding a touch of nature to the space.
Apartment in Evanston
4.72 out of 5 average rating, 121 reviews

Modern|Aesthetic|2BR|Evanston|Near Beach

MatthewRating, 5 stars1 week ago
Demitri is an extremely responsive and friendly host. All of my communications were responded to within 10 minutes. The apartment is as described and looks like the pictures. Other reviews mention street noise and they are correct - the apartment is right on a busy road. The street noise did not bother us but if you're sensitive to such things you should take that into consideration. You can also hear the upstairs neighbor walking (stomping lol?) around a lot. So another thing to consider if that might bother you. The area is very walkable: multiple restaurants on Main Street are within a 15 minute walk, and several Lake Michigan parks are literally around the corner. The L light rail station is also about a 15 minute walk away. We didn't have (or need) a car during our stay (Demitri let us drop our luggage off early). Strong and reliable WIFI internet. A nice apartment in a great location for the price.
Superhost
A historic manor house is seen adorned with lush greenery and beautiful landscaping. The structure features multiple balconies and large windows, highlighting the charm of its architectural design. A manicured lawn stretches in front, creating a serene setting.
Guest suite in Evanston
4.82 out of 5 average rating, 100 reviews

Historic Manor House Private Guest Suite Evanston

RebekahRating, 5 stars7 months ago
Charming and Historic. The house is on a quiet streat in a beautiful area. Janet's place is an easy drive to everything Chicago or a quick walk to the beach. Evanston has great restaurants and shops too.
Superhost
A bright living area features a light-colored sofa accompanied by a dark green armchair. A coffee table with decorative items sits in front of the couch. Framed artwork adorns the walls, and large windows allow natural light to fill the space.
Apartment in Evanston
4.85 out of 5 average rating, 65 reviews

Modern|Spacious|New Renovation|1BR|Evanston

Ana ClaudiaRating, 5 stars1 week ago
We loved staying in this apartment. Everything was super clean and organized, and the hosts helped us with everything we needed. The location is great, close to the lake, perfect for walks, runs, and enjoying the outdoors in Evanston. We would definitely come back!

Luxury beachfront home rentals

Superhost
A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.
Condo in Chicago
4.87 out of 5 average rating, 195 reviews

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

LeannRating, 5 stars2 months ago
WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!
Guest favorite
The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.
Townhouse in Chicago
4.84 out of 5 average rating, 206 reviews

Historic lux Townhouse on Chicago's Gold Coast

RobynRating, 5 stars6 days ago
The house was beautiful and in a very nice, safe neighborhood. There was some construction going on next door, but other than that, the place was everything we hoped it would be. We stayed here while we got married at a nearby venue in River North and it was able to accommodate our bridal party during our getting ready session and provide a quiet place to rest once our wedding was over.
A charming gray two-story home features a welcoming yellow front door. The porch is adorned with potted flowers, and large windows allow natural light to enter. The surrounding landscape includes well-maintained shrubs, creating an inviting approach to the entrance.
Home in Chicago
4.84 out of 5 average rating, 32 reviews

Only Urban Beach House in Chicago

TienRating, 5 stars10 months ago
This is a beautiful, old house right by the park and beach, plus a playground and adorable summer snack shack just a few minutes walk away. There's a lovely private back yard and deck for summer evenings. We especially appreciated the kitchen, which was well-stocked with all the dishes and equipment we needed to cook full meals for our large family. We stayed for an extended time, and whenever anything came up, our wonderful hosts were quick to respond and help. Thanks Keith for your hospitality!
Guest favorite
A private patio provides a cozy seating area featuring a 3-seater sofa and two accent chairs. A round coffee table sits in the center, with the urban street view visible beyond the wrought iron railing.
Apartment in Chicago
4.97 out of 5 average rating, 63 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Views

AmyRating, 5 stars2 days ago
Rasheed’s place is absolutely lovely. Very clean, lots of room for our family of 6 and we felt right at home. It’s in a great location, lots of restaurants and shopping and so close to Oak St beach. We found a market (potash) around the corner and the kitchen is well stocked and very nice and clean to cook in. There was coffee for both drip and keurig. Rasheed is a 5 star host. Quick to respond to questions and very helpful and accommodating. We definitely recommend this place and hope to be back soon.

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