Waterfront holiday rentals in Chicago Loop

4.82 out of 5 average rating, 212 reviews

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.

Flat in Streeterville

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!

Townhouse in Magnificent Mile

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.

4.84 out of 5 average rating, 225 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!

4.92 out of 5 average rating, 271 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.

Flat 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.

4.95 out of 5 average rating, 142 reviews

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.

Apartment in Gold Coast

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

4.95 out of 5 average rating, 44 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

4.78 out of 5 average rating, 51 reviews

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.

Flat in East Rogers Park

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.

4.82 out of 5 average rating, 234 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.

Flat in Chicago 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, 162 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, 108 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.

Flat 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! ✨

Apartment 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, 272 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.

4.89 out of 5 average rating, 107 reviews

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.

Flat in Uptown

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

Spacious high-quality 2-bed/2-bath in the heart of Uptown Chicago. Minutes walk from Lakeshore drive, Lakefront/beach, Recreation parks, the Riviera, Aragon Ballroom, and the Green Mill Cocktail Lounge (Al Capone's fave). You can drive 10 minutes to Downtown-Chicago or jump on the Redline, a Chicago L-train classic, which is a short stop to Wrigleyville (go Cubs!), the Loop, and more. Guest have access to the entire condo as well as parking garage.

4.89 out of 5 average rating, 110 reviews

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.

Flat in Evanston

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

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!

Popular amenities for waterfront rentals in Chicago Loop

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Flat in Near North Side

8BR Retreat for Groups w/ Easy City Access

Flat in Chicago

New place to stay

Upscale High-Rise Apt · Rooftop Pool + Views

4.79 out of 5 average rating, 29 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.

Flat in Englewood

The Wine Down

4.98 out of 5 average rating, 63 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.

Flat 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.

Flat in South Loop

4.66 out of 5 average rating, 154 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.

Flat in Evanston

4.8 out of 5 average rating, 193 reviews

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

4.9 out of 5 average rating, 196 reviews

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.

Flat in East Rogers Park

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.

Flat in Albany Park

4.77 out of 5 average rating, 161 reviews

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

Waterfront house rentals

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.

Private room in Burr Ridge

An aerial view of the custom-designed home showcases expansive lawns and a winding driveway. Nearby, serene water is visible, surrounded by trees and other residences. The architectural details of the house, including a prominent roof and large windows, highlight its blend of traditional and contemporary styles.

5 out of 5 average rating, 8 reviews

Tranquility Awaits You!

Private room in East Rogers Park

The spacious bedroom features a queen bed dressed in white bedding against a deep blue wall. Large windows with sheer curtains allow natural light, complementing the traditional furnishings, including a wooden dresser, a desk with a lamp, and a television.

4.94 out of 5 average rating, 50 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

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

A spacious room is illuminated by ceiling lights, featuring a cozy gas fireplace against a textured stone wall. A comfortable bed is complemented by a reading nook with a chair, and a bookshelf filled with various items and books is present on one side.

Private room in Park Ridge

4.65 out of 5 average rating, 20 reviews

Nice, large sunny garden studio

Private room in South Shore

A spacious sleeping area features a large bed with a pink quilt and decorative pillows. Natural light filters through multiple windows, illuminating the room. A television is mounted on the wall opposite the bed, with a dark wooden dresser nearby, creating a functional and inviting space.

Large King Suite/Terrace in Lakefront Rooftop-home

Waterfront apartment rentals

4.76 out of 5 average rating, 181 reviews

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.

Apartment in Lake View

Modern Wrigley Oasis with Parking!

Apartment 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

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.

Apartment in Burbank

Iconic Style, Charming Lake View

4.86 out of 5 average rating, 204 reviews

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.

Apartment in Gold Coast

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

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.

Apartment 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.

Apartment in Oak Lawn

Best view and luxury style, Located in Downtown

4.84 out of 5 average rating, 45 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.

Apartment in Bronzeville

Bronzeville Tribe Palace Loft