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Waterfront vacation rentals in Chicago Loop

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chicago Loop

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

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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 Gold Coast

4.82 out of 5 average rating, 202 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!

The living room features a comfortable gray sofa and a wooden coffee table set on a soft area rug. A Smart HDTV is positioned against a wall, while natural light enters through a large window adorned with light curtains. Decorative lighting fixtures enhance the space.

Vacation home in South Shore

4.94 out of 5 average rating, 79 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

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 Magnificent Mile

4.83 out of 5 average rating, 214 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

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 Lake View

4.92 out of 5 average rating, 250 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.

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 Gold Coast

4.95 out of 5 average rating, 127 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

Top guest favorite

A spacious living area is illuminated by natural light, featuring large windows that frame views of greenery outside. A modern sofa and armchair sit around a round coffee table, while a sleek fireplace adds warmth to the elegant decor.

Home in Gold Coast

5 out of 5 average rating, 38 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – 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 leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

The bright living area is enhanced by large windows allowing natural light to fill the space. A blue sectional sofa and two armchairs provide comfortable seating. A ceiling fan is visible above, and a TV is mounted on the wall. The dining area is seen in the background.

Apartment in East Rogers Park

4.79 out of 5 average rating, 39 reviews

Spacious & Elegant N Side Apt Near Beach & Transit

This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

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 The Loop

4.82 out of 5 average rating, 217 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!

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 Old Town

4.91 out of 5 average rating, 144 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.

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 Near West Side

4.98 out of 5 average rating, 125 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! ✨

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 East Rogers Park

4.93 out of 5 average rating, 254 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.

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Condo in Gold Coast

4.89 out of 5 average rating, 163 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.

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Popular amenities for Chicago Loop waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A stylish bedroom features a four-poster bed centered on a spacious wooden floor. Soft lighting from string lights creates a warm ambiance. A closet is visible in the corner, providing additional storage space, while natural light enters through a nearby window.

Apartment in East Rogers Park

4.93 out of 5 average rating, 43 reviews

Sheridan Beach Apartment

The living area features large windows allowing natural light to fill the space, showcasing city views. A comfortable double sofa bed, two accent chairs, and a minimalist coffee table are arranged on a light area rug. A flat-screen TV is mounted on the wall.

Apartment in The Loop

New place to stay

Top-Notch 2BR: The Bean View, Loop, Balcony

A spacious living area features large windows showcasing city views. A modern sofa with accent pillows faces a flat-screen TV, while stylish teal chairs complement the minimalist design. The open layout connects to a fully equipped kitchen visible in the background.

Apartment in River North

4.76 out of 5 average rating, 33 reviews

3BR Luxury Modern Apartment

A cozy living area features a soft sectional sofa facing a low coffee table on a colorful area rug. Natural light filters through large windows, illuminating the modern kitchen area in the background, defined by sleek cabinetry and stainless-steel appliances.

Apartment in Bridgeport

4.98 out of 5 average rating, 54 reviews

Cozy Chicago Apartment next to the River

A living area features a brown leather sofa with decorative cushions, complemented by a light-colored armchair. A wooden coffee table rests on a green area rug. A television is positioned nearby, with natural light entering through expansive windows.

Apartment in The Loop

4.7 out of 5 average rating, 137 reviews

Cozy 1BR in South Loop | Convenience in the City

A spacious living room features a cozy seating area with two leather sofas facing a modern TV stand. A light-colored coffee table is positioned between the sofas, and a decorative painting hangs above the fireplace. Large windows with blinds allow natural light to fill the space.

Apartment in Uptown

4.88 out of 5 average rating, 88 reviews

Elegant 2-bed/2-bath in the heart of Uptown

A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.

Apartment in Evanston

4.91 out of 5 average rating, 96 reviews

New renovation|1BR|Stylish|Modern|Next to the Lake

A bright living area features large windows allowing natural light to fill the space. A turquoise sofa and a gray couch are complemented by colorful cushions. A wooden coffee table rests on a patterned rug, surrounded by decorative plants and modern lighting.

Apartment in Irving Park

4.79 out of 5 average rating, 148 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Waterfront house rentals

A spacious room is highlighted by a large couch facing a television stand, surrounded by bookshelves filled with books. A bed with neutral bedding is positioned in the corner, and a desk with a lamp is set nearby. Soft lighting creates a bright atmosphere.

Private room in Lake View

4.88 out of 5 average rating, 141 reviews

Beautiful space in historic house near lakefront.

A historic Chicago home is showcased with a striking turquoise bay window and decorative accents. The structure features a combination of red brick and stone details. Large windows allow for light visibility through the interior, while the entrance displays a solid green door.

Home in Kenwood

5 out of 5 average rating, 9 reviews

Gem Near Hyde Park/McCormick Place/Beach

The exterior of a two-story brick home is viewed from a well-maintained lawn. A wooden deck extends from the house, with surrounding greenery complementing the serene lake in the background under a clear blue sky.

Home in Prospect Heights

4.91 out of 5 average rating, 56 reviews

Bike & Kayak: Lakefront Prospect Heights Home

A light-filled entryway displays a striking staircase with dark wooden steps and a crisp white wall. Marble flooring complements the modern aesthetic, while a glass door leads to the outside. Decorative wall sconces provide warm lighting along the staircase.

Home in Chicago

4.88 out of 5 average rating, 58 reviews

CasaNova Modern City Living

Private room in East Rogers Park

4.94 out of 5 average rating, 47 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

A cozy bedroom features a spacious bed adorned with a floral-patterned coverlet. Flanking the bed, two bedside lamps provide soft lighting. A large bookshelf filled with books lines the wall, and a window allows natural light to brighten the room.

Private room in Uptown

4.96 out of 5 average rating, 106 reviews

Comfortable private room near Lake and transit.

A spacious bedroom features a tufted beige headboard with a crisp white bedspread, complemented by warm wooden bedside tables. Natural light filters through large windows, accentuated by soft curtains. A decorative piece with a nature theme adorns the wall, and a small bench sits at the foot of the bed.

Home in West Town

5 out of 5 average rating, 7 reviews

Spacious house patio/free parking

The exterior of a red brick building is displayed, featuring large arched windows and a central entrance with steps leading up to it. Flanking structures are visible, showcasing a blend of architectural styles, while a sparse lawn with minimal landscaping is present in the foreground.

Home in Chicago

4.82 out of 5 average rating, 82 reviews

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

Waterfront condo rentals

A well-lit living space features large windows allowing natural light. A green sofa and two white chairs are arranged around a circular coffee table. A round dining table with wooden chairs is positioned nearby, and a soft area rug adds warmth to the hardwood floor.

Condo in Lake View

4.79 out of 5 average rating, 171 reviews

Modern Wrigley Oasis with Parking!

The studio apartment features a spacious open layout with a comfortable bed, muted bedding, and a nightstand. A TV is positioned on a modern media unit, and a mini fridge adds convenience. Natural light filters in through a window, illuminating the neutral decor.

Condo in Magnificent Mile

4.7 out of 5 average rating, 236 reviews

Studio flat in the heart of Chicago's Gold Coast

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Condo in Gold Coast

4.87 out of 5 average rating, 197 reviews

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

Top guest favorite

A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.

Condo in East Rogers Park

5 out of 5 average rating, 60 reviews

Where you want to BE! Stylish, Comfy, Luxe

A spacious living area is presented, featuring a gray sectional sofa adorned with decorative pillows. A glass coffee table sits at the center, complemented by two black accent chairs. Natural light filters through the nearby windows, enhancing the room's openness.

Condo in Wicker Park

4.78 out of 5 average rating, 27 reviews

Spacious Wicker Park Hideaway with Parking!

A bright living area features a blue sectional sofa facing a television. Two armchairs are positioned across from the seating area, with a glass coffee table in the center. Natural light streams in through two large windows, and a green plant adds a touch of nature.

Condo in Near North Side

4.82 out of 5 average rating, 113 reviews

River North Hideaway w/Amazing Views and Parking

A modern living area is observed, featuring a neutral sectional couch facing a large wall-mounted TV. A dining table is set with dark plates and decorative elements. Natural light streams through multiple windows, highlighting the sleek black and white decor.

Condo in Bronzeville

4.83 out of 5 average rating, 42 reviews

Bronzeville Tribe Palace Loft

Quick stats about waterfront rentals in Chicago Loop

Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
520 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore