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Condo vacation rentals in Chicago

Find and book unique condos on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chicago condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Superhost
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in East Pilsen
4.83 out of 5 average rating, 138 reviews

816 PLZN Luxury Apartment| Rooftop| Garage Parking

Guest favorite
A comfortable living area features an orange sofa and a variety of artwork on the walls. A round coffee table sits in the center of a patterned area rug. Natural light filters through the window shades, enhancing the welcoming vibe of the space.
Condo in Logan Square
4.95 out of 5 average rating, 101 reviews

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Guest favorite
A spacious living room features floor-to-ceiling windows that allow ample natural light, showcasing views of the city. A large gray sectional sofa is complemented by a cozy yellow armchair. A wall-mounted television is situated above a built-in fireplace, with a private balcony visible through sliding doors.
Condo in West Town
4.95 out of 5 average rating, 124 reviews

Your perfect place looks like?

Guest favorite
A modern living space features a sleek kitchen island with a sink, surrounded by light wood flooring. Large windows invite natural light, illuminating a comfortable gray sofa and a dining table with black chairs. A vibrant wall art piece adds color to the room.
Condo in Old Town Triangle
4.94 out of 5 average rating, 106 reviews

NEW luxury Old Town 1-Bedroom condo

Guest favorite
A spacious bedroom is equipped with a large bed featuring decorative pillows. On either side of the bed, warm lamps provide soft lighting. Above the bed, two framed art pieces display botanical themes, adding a touch of nature to the decor. A neutral-colored bench is placed at the foot of the bed.
Condo in East Pilsen
4.94 out of 5 average rating, 140 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Guest favorite
The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island provides extra counter space with two black stools positioned nearby. The open layout allows a view of the adjoining living area through a doorway.
Condo in North Side
4.91 out of 5 average rating, 128 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Superhost
The living and dining area features a sectional sofa and a futon, complemented by a decorative area rug. A television is positioned on a media console, and a dining table with upholstered chairs is visible. Natural light enters through high windows, enhancing the spacious feel.
Condo in West Town
4.86 out of 5 average rating, 267 reviews

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Superhost
A spacious living area is highlighted by a large sectional sofa positioned around a light area rug. Natural light filters through the floor-to-ceiling windows, while a sleek TV is mounted on the wall. Decorative plants and modern furnishings add to the inviting atmosphere.
Condo in Chicago
4.83 out of 5 average rating, 158 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

Pet-friendly condo rentals

Guest favorite
A living area features two tufted gray sofas and a glass coffee table atop a patterned rug. The space is illuminated by natural light from large windows, with decorative accents including throw pillows and a cozy ottoman.
Condo in North Side
4.83 out of 5 average rating, 375 reviews

Chic and Charming Vintage Condominium in Lincoln Park

Guest favorite
A spacious living area is highlighted by large windows offering expansive views of the city skyline. A comfortable sofa and two accent chairs are positioned around a coffee table. A dining table with several chairs is visible beside a colorful wall art piece that adds a touch of personality.
Condo in Grant Park
4.82 out of 5 average rating, 141 reviews

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Superhost
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
4.71 out of 5 average rating, 241 reviews

Studio flat in the heart of Chicago's Gold Coast

Guest favorite
A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.
Condo in Bridgeport
4.91 out of 5 average rating, 128 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in Humboldt Park
4.93 out of 5 average rating, 134 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Guest favorite
A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.
Condo in Oak Park
4.93 out of 5 average rating, 267 reviews

Picture Perfect 3Bed Steps from Train and FLW

Superhost
A modern kitchen area features white cabinetry and a central island equipped with a sink and stools. Stainless steel appliances are visible alongside a decorative backsplash. Natural light fills the space through overhead lighting and a nearby entryway.
Condo in Lower West Side
4.84 out of 5 average rating, 130 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

Guest favorite
A spacious living area features a large flat-screen television and a circular glass coffee table, surrounded by comfortably upholstered seating. Natural light floods in through glass block windows, highlighting the open design that connects to a fully-equipped kitchen in the background.
Condo in Chicago
4.87 out of 5 average rating, 277 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

Condo rentals with a pool

Guest favorite
An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 114 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Superhost
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Condo in Lombard
4.83 out of 5 average rating, 64 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village
4.91 out of 5 average rating, 92 reviews

Just remodeled apartment close to airport and mall

Guest favorite
An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.
Condo in Evanston
4.92 out of 5 average rating, 130 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 107 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

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

Superhost
A light-filled living area features a comfortable beige sofa adorned with decorative pillows. A coffee table sits in front, holding a plant and tray. In the background, a kitchen with wooden cabinets and bar stools is visible, complementing the modern aesthetic.
Condo in Downers Grove
4.88 out of 5 average rating, 56 reviews

Upscale, Smoke and Pet Free, Washer Dryer, Balcony

Quick stats about condo rentals in Chicago

  • Total rentals

    1K properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    70K reviews

  • Family-friendly rentals

    630 properties are a good fit for families

  • Pet-friendly rentals

    300 properties allow pets

  • Rentals with a pool

    80 properties have a pool

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