Beachfront vacation rentals in Oak Street Beach

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Oak Street Beach

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Guest favorite

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.

Oct 25 – Nov 1

€ 586 per night

Guest favorite

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 1 – 8

€ 334 per night

Apartment in Chicago

Gorgeous N. Kenwood/Hyde Park

The whole group will enjoy easy access to everything from this centrally located place. The unit is 3bdrm 2bths, 1800sq ft located on the second floor, located in North Kenwood/Hyde Park area. Accessible to major CTA bus/train, the metra, and with a 20 minute commute via public transportation or 12 minute car ride to the loop. Directly across from Lake Michigan bike/walking path and beach area. Located within 1.5 miles of 5 grocery stores and restaurants in both Hyde Park and Bronzeville area.

Mar 7 – 14

€ 568 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

€ 387 per night

Guest favorite

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!

Oct 18 – 25

€ 1,266 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!

Nov 23 – 30

€ 392 per night

Apartment in Chicago

4.81 out of 5 average rating, 36 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!

Aug 6 – 13

€ 226 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 15 – 22

€ 1,010 per night

Guest favorite

Apartment in Chicago

5.0 out of 5 average rating, 5 reviews

Gold Coast Pristine Paradise 3BR/2BA. Free Parking

FREE GARAGE PARKING!! Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone's throw away from Oak Beach.

Jan 15 – 22

€ 724 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

€ 208 per night

Guest favorite

Apartment in Chicago

4.88 out of 5 average rating, 86 reviews

Cannabis Condo 4BR

Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for summer time Chicago!

Sep 11 – 18

€ 341 per night

Cottage in Gary

4.11 out of 5 average rating, 28 reviews

Lake Street Home-A short reach to the beach!

Lake Street Beach Home is "The Place" for Jet Skiing, Boating, Sailing. This beautiful beach home is located 200 ft(0.1 mi) from Lake Michigan which gives you a great time in any season. You will enjoy the Sunsets over Chicago!!! Boutiques, SeaDogs’ food truck, galleries, D&K Salads, Tequila & Tacos, Vibrations' healthy delicious smoothies-in which majority of the specialty shops are South bound on Lake Street. Sorry no pets!

Oct 1 – 8

€ 321 per night