Waterfront vacation rentals in Chicago River

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chicago River

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

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Superhost

A rooftop terrace features various seating options, including lounge chairs and circular lounges. Colorful cushions are arranged on some seats, while green planters add a touch of nature. The skyline of Chicago is visible in the background under a clear blue sky.

Apartment in Chicago

4.82 out of 5 average rating, 191 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

The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.

Townhouse in Chicago

4.84 out of 5 average rating, 199 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

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Chicago

4.92 out of 5 average rating, 227 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.

Top guest favorite

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Condo in Chicago

4.95 out of 5 average rating, 116 reviews

Modern MAG Mile 2BD/2BA (+Parking/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 - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

Superhost

The living area features a light-colored sofa paired with two cozy armchairs. A round coffee table sits at the center on a colorful area rug. Natural light floods the space through two large windows, and decorative plants are placed on the windowsills.

Apartment in Chicago

4.81 out of 5 average rating, 196 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

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

Townhouse in Chicago

4.94 out of 5 average rating, 126 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

A modern living room features a light gray sofa paired with dark accent pillows. Natural light fills the space through large windows, complemented by dark curtains. A stylish armchair and a side table sit next to the sofa, while a flat-screen TV is mounted on the wall.

Apartment in Chicago

4.97 out of 5 average rating, 115 reviews

Free Parking| King Bed |Private Balcony |Sleeps 8

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

Top guest favorite

A spacious bedroom features a large bed with soft bedding and multiple pillows. Dark walls create a cozy ambiance, complemented by stylish artwork. A glass table and chairs are visible, along with a modern ceiling fan and a bright window providing natural light.

Apartment in Chicago

4.95 out of 5 average rating, 80 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This lovely 3 bedroom, 2 bath unit has a large front balcony and also a rear deck looking out to the lake. The unit has an updated kitchen & 2 baths, a dining area, in unit laundry & a spacious living room with a fireplace & lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is a short walk down Sheridan. Kayak/paddle board rental available (May 1-Oct 15th), weather permitting.

Guest favorite

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

Condo in Chicago

4.92 out of 5 average rating, 231 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy 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. Note: no full kitchen.

Guest favorite

Townhouse in Westmont

4.87 out of 5 average rating, 130 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.

Top guest favorite

A modern kitchen bar opens to a dining area, featuring a sleek countertop with four stools. A spacious living room is visible, complemented by natural light streaming through large windows. Decorative art pieces adorn the walls, enhancing the overall aesthetic.

Home in Chicago

5 out of 5 average rating, 71 reviews

NEW! Lake & Skyline View on Kenwood Culdesac!

Modern luxury awaits you in this Urban Oasis. New construction with all new finishes and stylish decor. Great natural light, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

Superhost

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!