Waterfront holiday rentals near Millennium Park

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!

4.94 out of 5 average rating, 88 reviews

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.

Holiday home in Chicago

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

4.84 out of 5 average rating, 231 reviews

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

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.

4.92 out of 5 average rating, 274 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 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, 9 reviews

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

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.

4.81 out of 5 average rating, 240 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!

4.91 out of 5 average rating, 165 reviews

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

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 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.

4.98 out of 5 average rating, 112 reviews

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! ✨

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.

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.

4.89 out of 5 average rating, 110 reviews

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.

Popular amenities for waterfront rentals near Millennium Park

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

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.

4.8 out of 5 average rating, 30 reviews

The Wine Down

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.

4.98 out of 5 average rating, 64 reviews

Cozy Chicago Apartment next to the River

A well-lit living room features a leather couch adorned with bright throw pillows, alongside a cozy chair. A decorative area rug covers the hardwood floor, with large windows providing natural light. A spiral staircase leads to the upper level, complemented by tasteful curtains.

4.79 out of 5 average rating, 33 reviews

Modern Cozy Top Floor Duplex near Wrigley

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.

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

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, 201 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.

4.76 out of 5 average rating, 162 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER 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

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, 9 reviews

Tranquility Awaits You!

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, 51 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.

4.96 out of 5 average rating, 109 reviews

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 wooden deck extends toward a serene lake, offering scenic water views. A table with several chairs is shaded by a large umbrella, providing a comfortable outdoor seating area. The surrounding landscape features trees with autumn foliage, enhancing the tranquil setting.

Home in Westmont

4.75 out of 5 average rating, 40 reviews

Cozy 5-bedroom with lake views and spacious deck

A gas fireplace is framed by a mosaic stone wall, adding texture to the room. Cozy seating is arranged nearby, featuring two patterned chairs with vibrant cushions. A wooden table stands adjacent to the fireplace, creating a versatile space for relaxation or dining.

Private room in Park Ridge

4.55 out of 5 average rating, 22 reviews

Nice, large sunny garden studio

Waterfront condo accommodation

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 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

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.

5 out of 5 average rating, 61 reviews

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.

4.81 out of 5 average rating, 127 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.

4.85 out of 5 average rating, 46 reviews

Bronzeville Tribe Palace Loft

4.8 out of 5 average rating, 61 reviews

MAG MILE MEGA Entire Floor 4BD/4BA (+Roof/Gym)

Other waterfront holiday rentals

A king-size bed is positioned against a textured grey wall, adorned with luxurious Gucci bedding. Soft ambient lighting is provided by wall sconces, while sheer curtains gently filter natural light from the side window. A pair of matching ottomans sits at the foot of the bed.

5 out of 5 average rating, 3 reviews

Fabulous Near McCormick Place Luxury Unit

4.82 out of 5 average rating, 51 reviews

Townhouse in Westmont

Couples retreat Duplex- Side B. In law suite 1/1

A heated indoor pool is accentuated by bright blue water, surrounded by light-colored tiles. Lounge chairs with lime green cushions are positioned along one side, offering a space for relaxation. Soft lighting enhances the ambiance, while large windows provide a view of the outdoors.

Hotel room in Oakbrook Terrace

4.54 out of 5 average rating, 160 reviews

Easy Access to Downtown| Free parking. Indoor Pool

4.77 out of 5 average rating, 93 reviews

A bright living area features a light-colored sofa accompanied by a dark green armchair. A coffee table with decorative items sits in front of the couch. Framed artwork adorns the walls, and large windows allow natural light to fill the space.

Apartment in Evanston

Modern | Spacious | New Renovation | 1BR | Evanston

South Loop Condo

4.83 out of 5 average rating, 53 reviews

Gold Coast Getaway (Rooftop Deck • Fitness Center)

The living area features a spacious gray sofa and a dark armchair, complemented by a light area rug. A glass coffee table is positioned nearby, and a tall plant adds texture. Natural light is welcomed through the windows, enhancing the calming wall colors.

4.64 out of 5 average rating, 11 reviews

Cozy 1BR Retreat | Near Transit, Dining & Parking!