Waterfront vacation rentals in Near North Side, Chicago

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Near North Side, Chicago

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

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Guest favorite

Home in Gold Coast

5 out of 5 average rating, 6 reviews

Gold Coast Pristine 4BR/4.5BA Home | Free Parking.

Luxurious Gold Coast Getaway – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for work or leisure, this property offers modern amenities and unforgettable comfort in the heart of downtown.

Superhost

Rental unit in Gold Coast

4.84 out of 5 average rating, 174 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

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. 1 min 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 Lake View

4.92 out of 5 average rating, 213 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, 216 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.

Superhost

Rental unit in East Rogers Park

5 out of 5 average rating, 3 reviews

Lux apartment near Michigan lake

Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming apartment offers a delightful blend of modern comfort and vibrant city living. Kitchen provides everything you need to prepare meals and we add baby cribs now for families. Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, and it is near by Evanston that provides many dinning options.

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, 175 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, 109 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

Condo in West Town

4.87 out of 5 average rating, 94 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, 148 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.