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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Superhost

Rental unit in Gold Coast

4.84 out of 5 average rating, 172 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

Rental unit in Lake View

4.92 out of 5 average rating, 212 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, 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 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.

Guest favorite

Condo in East Rogers Park

4.93 out of 5 average rating, 215 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

Guest suite in Carol Stream

4.94 out of 5 average rating, 288 reviews

Cozy Lakefront Retreat: Hot Tub & Bar/Pool Table

Very large guest suite with 3 separate areas. Just like your own apartment. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement apartment but you have complete privacy down there. Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! (Full kitchen & laundry room are shared space)

Guest favorite

Vacation home in South Shore

4.97 out of 5 average rating, 60 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

Guest favorite

Rental unit in East Rogers Park

4.88 out of 5 average rating, 114 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 Naperville

4.95 out of 5 average rating, 366 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Superhost

Rental unit in Gold Coast

4.84 out of 5 average rating, 43 reviews

MAG MILE/Gold Coast Getaway (+Rooftop/Gym)

Welcome! 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. We look forward to hosting you!

Superhost

Rental unit in The Loop

4.79 out of 5 average rating, 172 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

Townhouse in Old Town

4.94 out of 5 average rating, 105 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Guest favorite

Rental unit in Evanston

4.89 out of 5 average rating, 44 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!

Superhost

Condo in Gold Coast

4.88 out of 5 average rating, 147 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.