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Condo vacation rentals in Cook County

Find and book unique condos on Airbnb

Top-rated condo rentals in Cook County

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

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Superhost
A spacious living area features an exposed brick wall complemented by large windows allowing natural light in. A sectional sofa is arranged around a round coffee table atop a patterned rug, and a modern light fixture hangs from the ceiling. A television is positioned on a clean-lined media console.
Condo in Lake View
4.87 out of 5 average rating, 150 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy
4.93 out of 5 average rating, 280 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favorite
Condo in Uptown
4.91 out of 5 average rating, 208 reviews

Sunny Top-Floor Uptown Condo Near Lake & Red Line

Bright top-floor Chicago condo with fast WiFi, dedicated workspace, and easy access to Montrose Beach and the CTA. Perfect for remote workers, couples, and travelers looking to experience Chicago like a local. Enjoy a sunny living room, fully equipped kitchen and dining room, spacious primary bedroom, and serene sunroom with a full-size bed. Just steps from the lakefront and a 6-minute walk to the 24/7 Wilson Red Line. Over 1,000 sq. ft. of comfortable living space in historic Uptown.

Top guest favorite
A modern dining area features a wooden table surrounded by six chairs. Natural light enters through large windows, highlighting the grey walls and stylish cabinetry. A chandelier hangs above the table, while a wall-mounted art piece adds a decorative touch to the space.
Condo in Wrigleyville
4.91 out of 5 average rating, 180 reviews

Foosball, Steps from Wrigley, Private Parking

Our apartment is ideally located near Wrigley Field and just steps from the Red Line, making it extremely convenient for exploring Chicago. Because of this prime location, occasional train and street noise can be heard. To help you sleep comfortably, we provide ear plugs. Many of our guests still enjoy the vibrant city atmosphere while finding the apartment cozy and restful. Perfect For: Guests who love being in the heart of Chicago and don’t mind a bit of city life sounds.

Guest favorite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in North Side
4.95 out of 5 average rating, 170 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Guest favorite
Condo in Wicker Park
4.96 out of 5 average rating, 118 reviews

Two Bedroom w Porch in Wicker Park

Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

Top guest favorite
A bright living room features large windows allowing natural light to fill the space. Comfortable seating includes a spacious couch and decorative poufs. A smart TV is mounted on the wall, and plants bring a touch of greenery, enhancing the relaxing environment.
Condo in North Side
4.99 out of 5 average rating, 159 reviews

Designer Avondale 2BR w/Easy Parking

Experience the Avondale Retreat, a sun-filled, stylish Chicago apartment perfect for couples or friends. This impeccably clean, first-floor space offers a comfortable layout, abundant natural light, and free street parking. Enjoy a full kitchen, two tranquil bedrooms with Parachute linens, a dedicated workspace, and fast Wi-Fi. Ideal for 2-4 guests seeking a relaxing base to explore the city.

Top guest favorite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Condo in Evanston
4.96 out of 5 average rating, 139 reviews

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

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

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, 352 reviews

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.

Top guest favorite
Condo in Downtown Chicago
4.91 out of 5 average rating, 344 reviews

Old Town Condo: Private Terrace & Garage Parking

Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.

Top guest favorite
A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.
Condo in Ravenswood
4.97 out of 5 average rating, 502 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. We live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Top guest favorite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Condo in Lake View
4.99 out of 5 average rating, 715 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

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