Waterfront vacation rentals in Chicago

Apartment in Streeterville

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.

4.81 out of 5 average rating, 216 reviews

The Lakefront Lookout (Rooftop Deck • Gym)

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!

Vacation home in Jackson Park Highlands

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.

4.94 out of 5 average rating, 87 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

4.92 out of 5 average rating, 274 reviews

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

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 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.

4.86 out of 5 average rating, 207 reviews

2BD/2BA MAG MILE MASTERPIECE (+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 - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

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.

4.95 out of 5 average rating, 147 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

5 out of 5 average rating, 8 reviews

Apartment in Chicago

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

4.91 out of 5 average rating, 47 reviews

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

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

Condo in Magnificent Mile

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.

4.71 out of 5 average rating, 247 reviews

Studio flat in the heart of Chicago's Gold Coast

Come stay in our one-bedroom studio apartment with a fully equipped kitchen and bathroom. Take in the perks of our central location with easy access to the Gold Coast beach and public transportation. Gibsons and the Original Pancake House are also a stone’s throw away. The property is the perfect refuge after a long day in the Windy City or sunbathing on the beach. After working hard and playing hard, a comfy bed with high-quality linens ensures you’ll be rested and ready for the next day.

4.81 out of 5 average rating, 240 reviews

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

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!

Townhouse in Near North Side

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.

4.91 out of 5 average rating, 165 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.

4.98 out of 5 average rating, 112 reviews

A modern living area features a gray sofa with accent chairs set beside large windows, allowing natural light. A patterned area rug covers the floor, complemented by a minimalist coffee table. Wall art adds subtle elegance, enhancing the overall inviting layout.

Apartment in West Town

Spacious&Modern Condo | Near Dwtn | Secure Parking

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! ✨

Condo in East Rogers Park

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.

4.93 out of 5 average rating, 275 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.

Popular amenities for Chicago waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in East Rogers Park

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.

4.88 out of 5 average rating, 51 reviews

Sheridan Beach Apartment

4.8 out of 5 average rating, 30 reviews

A sleek glass side table is adorned with travel books featuring cities like Paris and London, accompanied by a decorative globe. Behind, a spacious gray sofa, accented with throw pillows, complements the indoor plants and softly filtered natural light from large windows.

Apartment in Englewood

The Wine Down

4.98 out of 5 average rating, 64 reviews

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 Chicago

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 South Loop

4.64 out of 5 average rating, 159 reviews

Cozy 1BR in South Loop | Convenience in the City

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

4.8 out of 5 average rating, 195 reviews

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

Apartment in East Rogers Park

An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.

4.9 out of 5 average rating, 200 reviews

Executive Apartment on Lake Michigan with parking

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 Albany Park

4.76 out of 5 average rating, 162 reviews

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

Apartment in East Rogers Park

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.

4.96 out of 5 average rating, 94 reviews

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

Waterfront house rentals

4.95 out of 5 average rating, 38 reviews

A bright bedroom features a spacious white bed with two pillows, positioned beneath a window that allows natural light to fill the space. A wooden nightstand holds a lamp, contributing to a serene atmosphere. The walls are painted in a soft green hue.

Private room in Roselle

quiet comfortable private room near ElginOhare exp

Private room in Lake View

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.

4.89 out of 5 average rating, 150 reviews

Beautiful space in historic house near lakefront.

4.92 out of 5 average rating, 64 reviews

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

Bike & Kayak: Lakefront Prospect Heights Home

4.9 out of 5 average rating, 70 reviews

A modern living area features a curved sofa and two armchairs, arranged around a circular, striped rug. A flat-screen TV is mounted on the wall above a sleek fireplace. Natural light enters through large windows, complementing a dining area with a round table and multiple chairs.

Home in Chicago

CasaNova Modern City Living

4.93 out of 5 average rating, 57 reviews

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

Lakefront View Getaway Home! Hot tub! Kayak!

4.96 out of 5 average rating, 109 reviews

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

Comfortable private room near Lake and transit.

4.82 out of 5 average rating, 85 reviews

The living area is styled with a gray sectional sofa adorned with decorative pillows. A coffee table occupies the center, surrounded by two armchairs. Bright light filters through large windows, contributing to a relaxed atmosphere.

Home in Chicago

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

A comfortable living area features a dark sectional sofa and a sleek coffee table positioned on a patterned rug. A flat-screen television is mounted opposite the seating, while a floor lamp and window provide soft illumination.

Home in Des Plaines

4.56 out of 5 average rating, 55 reviews

House 1 minute from O'hare Airport

Waterfront condo rentals

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.

4.9 out of 5 average rating, 174 reviews

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

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

5 out of 5 average rating, 61 reviews

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 Edgewater

Where you want to BE! Stylish, Comfy, Luxe

The spacious bedroom features a king bed with soft bedding, complemented by an accent chair and a lamp. Large windows offer a panoramic view of Chicago’s skyline, allowing natural light to fill the room while city details are visible outside.

Condo in Oak Lawn

Best view and luxury style, Located in Downtown

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

4.81 out of 5 average rating, 127 reviews

River North Hideaway w/Amazing Views and Parking

4.85 out of 5 average rating, 46 reviews

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

Bronzeville Tribe Palace Loft