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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Guest favorite

The exterior of a red brick building showcases a classic architectural design with white-framed windows. The front steps lead to a dark door, surrounded by well-maintained shrubs and small plants. Clear blue skies create a bright backdrop to the inviting facade.

Condo in Chicago

4.96 out of 5 average rating, 117 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 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. Free parking on Lawndale Ave.

Guest favorite

A modern kitchen displays sleek dark cabinetry and stainless steel appliances. An island countertop is accompanied by transparent bar stools, while a dining area features a black table with tall stools. A light pastel wall is adorned with a playful accent, creating an inviting space.

Condo in Chicago

4.88 out of 5 average rating, 393 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Guest favorite

An outdoor space features a wooden deck leading to a staircase, surrounded by exposed brick walls. A circular fire pit is centered among four chairs, with a hot tub and seating area visible in the background. Green shrubs accent the concrete patio.

Condo in Chicago

4.94 out of 5 average rating, 208 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

A stainless steel spice rack is displayed on a textured granite countertop. The rack holds various spice jars in a circular arrangement, labeled with names such as 'Italian Seasoning' and 'Oregano.' A sleek electric wine opener rests nearby, featuring a modern design.

Condo in Chicago

4.87 out of 5 average rating, 127 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Guest favorite

A modern three-story condominium is showcased, featuring a combination of dark and light brick with large windows. Soft lighting highlights the front entrance and landscaped gravel area, providing a contemporary appeal. Neighboring buildings are visible in the background, contributing to the urban atmosphere.

Condo in Chicago

4.92 out of 5 average rating, 166 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

The space has been intentionally designed to offer a modern, yet comfortable feel for individual guests or families. Conveniently located just 6 miles south of Magnificent Mile, 5.6 miles from Navy Pier, 1 mile to Lake Shore Drive, 1.5 miles from the University of Chicago, 2 miles from Museum of Science and Industry, 1.2 miles from the many restaurants on 53rd Street in Hyde Park and close to many Chicago favorites! On-street parking available directly in front of the building.

Guest favorite

A sandy beach scene is captured with gentle waves lapping at the shore and people enjoying the water. In the foreground, a couple stands together, gazing out at the sea. Large, fluffy clouds drift above, adding to the serene atmosphere.

Condo in Chicago

4.93 out of 5 average rating, 243 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.

Superhost

The exterior of the building features a modern brick facade, showcased against a twilight sky with hues of purple and pink. Large windows reflect the surrounding cityscape, while a blue awning with the property name adds a distinctive touch to the entrance.

Condo in Chicago

4.75 out of 5 average rating, 120 reviews

Cabin 101 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Guest favorite

A modern kitchen showcases streamlined cabinetry in contrasting black and white. A large wooden dining table is paired with black seats. Decorative plants and soft lighting enhance the inviting ambience. Exposed wooden beams add warmth to the contemporary design.

Condo in Chicago

4.95 out of 5 average rating, 109 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Superhost

A two-story brick building is featured, showcasing a warm facade with detailed architectural accents. A set of wooden stairs leads to the entrance, surrounded by a landscaped yard and a pathway. Neighboring buildings share a similar design, contributing to a harmonious streetscape.

Condo in Chicago

4.84 out of 5 average rating, 199 reviews

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Guest favorite

Condo in Oak Park

4.94 out of 5 average rating, 243 reviews

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Instagram-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

A charming three-story brick building is surrounded by greenery, featuring ivy climbing its walls. Large windows are visible on each floor, allowing natural light to permeate the space. The walkway leads to a welcoming entrance, framed by shrubs and seasonal flowers.

Condo in Chicago

4.99 out of 5 average rating, 639 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 a newly remodeled 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.

Guest favorite

A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.

Condo in Chicago

4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

This freshly remodeled condo with European flair is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.