Waterfront vacation rentals in Chicago

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chicago

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in Lake View

4.91 out of 5 average rating, 201 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.

Superhost

Rental unit in Gold Coast

4.86 out of 5 average rating, 162 reviews

The Lakefront Lookout (2BR)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Guest favorite

Townhouse in Magnificent Mile

4.81 out of 5 average rating, 170 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!

Guest favorite

Condo in East Rogers Park

4.93 out of 5 average rating, 197 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Dogs only. Parking free on street or one spot for a fee.

Guest favorite

Vacation home in South Shore

4.96 out of 5 average rating, 52 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. Walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Superhost

Rental unit in East Rogers Park

4.87 out of 5 average rating, 107 reviews

Rock Star Beach Pad on Lake Michigan with parking

Live like a Rock Star! Stay in a celebrity 2br 2bath apartment with its own beach on Lake Michigan. The apartment is on the 2nd floor in a walk-up building consisting of 5 short-term rental apartments. 2 apartments on each floor. The apartment has direct water views with a shared porch with a -Free Onsite Parking with EV Charging Station -Steps away from parks and minutes to restaurants universities and shopping -Less than 20 min drive to Wrigley Field, Downtown Chicago, and museums.

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 222 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Superhost

Rental unit in The Loop

4.78 out of 5 average rating, 156 reviews

Spacious & Stylish 2BR-2BA Apt Steps from The Bean

Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Guest favorite

Rental unit in East Rogers Park

4.94 out of 5 average rating, 17 reviews

Sheridan Beach Apartment

Keep it central at this place! This basement apartment not only comes fully stocked with an in-unit washing machine, but a full kitchen with all new appliances. The unit is a PRIVATE apartment in a single-family home that is 10 steps away from the nearest CTA Bus stop, 2 blocks away from the redline, and ONLY 100 STEPS AWAY FROM THE BEACH on Lake Michigan 😄 Any and all drug use is a prohibited here. Any and all pets are prohibited here as this is a clean and newer construction.

Guest favorite

Condo in West Town

4.87 out of 5 average rating, 93 reviews

Upscale Penthouse Private Balconies Amazing Views

My place is conveniently located in East Village, situated between the cultural hubs of Wicker Park and West Town & not far from downtown. Even with some of Chicago's best restaurants nearby, you'll love my spacious and fully stocked kitchen. You can also enjoy the giant shower and bathtub and take in the beautiful Chicago skyline with 2 private, outdoor decks. Public transportation and many local shops are just a short walk away! There a 4 flights of stairs.

Superhost

Condo in Gold Coast

4.89 out of 5 average rating, 141 reviews

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

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Guest favorite

Townhouse in Westmont

4.87 out of 5 average rating, 128 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.