Beachfront vacation rentals in North Side

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in North Side

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 182 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room off the kitchen has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Nov. 2 – 9

$720 CAD per night

Guest favourite

Guesthouse in Evanston

4.94 out of 5 average rating, 96 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house . Extra

Sep. 12 – 19

$540 CAD per night

Guest favourite

Home in Highland Park

4.92 out of 5 average rating, 39 reviews

Witness Sunrise Over Lake Michigan

Mesmerizing views of Lake Michigan from nearly every corner of this recently renovated Mid-Century Modern home. The house is walking distance from Ravinia Festival, downtown Ravinia Restaurants, and glorious Rosewood Beach; a healthy walk or short drive from Metra Train Stn. to Chicago and from the Chicago Botanical Gardens. Of course, guests can always choose instead to relax fireside, on the roof deck, or at the home’s private beach. Perfect for 4 guests, it accommodates 6. 2K, 2Q, 2.5 baths.

Oct. 1 – 8

$1,689 CAD per night

Superhost

Townhouse in Chicago

4.8 out of 5 average rating, 154 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

Nov. 15 – 22

$1,069 CAD per night

Superhost

Condo in Chicago

4.9 out of 5 average rating, 167 reviews

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

May 7 – 14

$562 CAD per night

Guest favourite

Townhouse in Chicago

5.0 out of 5 average rating, 209 reviews

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Apr. 7 – 14

$1,764 CAD per night

Guest favourite

Home in Cary

4.9 out of 5 average rating, 50 reviews

White Turtle on Fox River welcomes you!

1-bed, 1-bath house on Fox river. King-size bed in bedroom and sleeper sofa in living room. Cathedral ceiling studio living room, kitchen with appliances and basic kitchen stuff are there for your convenience. Fire pit, gas grill, deck and river view concrete patio will help you enjoy outdoor fun for you and your kids. Several forest preserves located around. 10 minutes walk distance to Cary Metra station which connects you to Chicago downtown. Close to shopping plazas and restaurants.

Oct. 12 – 19

$298 CAD per night

Guest favourite

Apartment in Chicago

4.86 out of 5 average rating, 50 reviews

Lakeview/Boystown/Wrigleyville Paradise Haven

In the heart of historic trendy Boystown and Wrigleyville, this fully furnished quiet 1 BR/1 BA apartment with an equipped kitchen is in a vibrant culturally diverse neighborhood. 6 Minutes drive to Downtown. It is steps from the beach, lakefront parks, and Belmont Harbor, and is within walking distance to many restaurants, boutique shops, amazing nightlife, many local theaters, and home of the World Series Champs, the CUBS. Enjoy a 65inches Samsung QLED Tv Netflix, Hulu, Apple Music.

Feb. 25 – Mar. 4

$284 CAD per night

Condo in Chicago

4.67 out of 5 average rating, 15 reviews

Modern Duplex Condo With Advanced 4K LED TV’s/PS5

Welcome to our urban oasis at the Contemporary Duplex Condo! Conveniently located, our Airbnb showcases Chicago-style brick accents in the living space. Enjoy modern conveniences, stylish decor, and plenty of natural light, crafting a warm and inviting atmosphere. With 1800 sqft of space, accommodating up to ten guests, it's perfect for solo travelers, couples, groups, and families. Secure your spot now for an authentic urban adventure, complete with a PS5!

Feb. 10 – 17

$558 CAD per night

Apartment in Chicago

4.8 out of 5 average rating, 35 reviews

Woodlawn Oasis

Welcome to Woodlawn Oasis! Come and enjoy the charm and warmth of this fully remodeled and furnished apartment with original artwork! Just 5 minutes from our beautiful Chicago lakefront, the prestiges University of Chicago, and soon to be Tiger Woods golf course and President Obama library. Also, 10 minutes from Chicago museums, Soldier Field (Chicago Bears), Guaranteed Rate Field (Chicago White Sox) and the fabulous night life of Downtown Chicago!

Jul. 22 – 29

$313 CAD per night

Home in Chicago

4.86 out of 5 average rating, 28 reviews

Only Urban Beach House in Chicago

Why stay in a hotel or dorm when you can have your own house! The Urban Beach House of Rogers Park, Chicago’s only urban beach house, has 4 bedrooms, 3 full baths, and is loaded with features that make it the perfect place for vacationers, students, faculty, family and gatherings of all kinds. Steps from the sandy beaches of Lake Michigan, walking distance from dozens of restaurants and shops, and minutes from 3 train stations and a Divvy bike station.

Feb. 13 – 20

$1,466 CAD per night

Superhost

Apartment in Evanston

4.86 out of 5 average rating, 28 reviews

Modern|Spacious|New Renovation|1BR|Evanston

Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen-sized bed, and a clean bathroom. Explore the nearby beaches, stroll along the lakefront path, and discover the vibrant downtown area with its shops and restaurants. Easy access to public transportation allows you to explore downtown Chicago. Book your stay now for a memorable Evanston getaway!

Jun. 18 – 25

$301 CAD per night