Condo vacation rentals in Chicago

Find and book unique condos on Airbnb

Top-rated condo rentals in Chicago

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Superhost

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 Avondale

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.

Superhost

Condo in Wicker Park

4.96 out of 5 average rating, 109 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Superhost

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 East Rogers Park

4.93 out of 5 average rating, 241 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

A spacious living area features high ceilings and large windows, allowing natural light to fill the space. A modern dining table sits center stage, surrounded by colorful chairs. A cozy seating area is visible, with a sectional sofa and contemporary decor enhancing the atmosphere.

Condo in West Loop

4.96 out of 5 average rating, 231 reviews

Updated Designer Duplex In Fulton Market W/parking

We completed our luxury renovation in kitchen, bathrooms, and patio with a fire pit! We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Superhost

An outdoor deck area is equipped with two black woven lounge chairs and a glass table, surrounded by wooden railing and greenery. The setting offers a relaxed space for guests to enjoy time outdoors, with exposed brick walls in the background.

Condo in Lincoln Park

4.76 out of 5 average rating, 308 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Stay in the heart of Chicago Old Town! This bright, cool and comfortable one bedroom, one bath is decked out in mid century modern furniture, exposed brick, new appliances and has a true city feeling! It comfortably sleeps two (3rd person can sleep on the couch), just 2 blocks to Lincoln Park, and 3 blocks to the famous Second City & stellar Old Town bars. Not to mention a quick 5 minute Uber ride to river north district (downtown Chicago)!

Superhost

The building exterior features a historic red brick façade, highlighted by large blue awnings over the entrance. The signage indicates '747 Lofts,' and the structure's three levels are visible. A sidewalk and nearby parked cars complement the urban setting.

Condo in West Town

4.81 out of 5 average rating, 155 reviews

Cabin 207 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!

Superhost

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 Wicker Park

4.95 out of 5 average rating, 107 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 Humboldt Park

4.84 out of 5 average rating, 198 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.

Superhost

Condo in Oak Park

4.94 out of 5 average rating, 242 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.

Superhost

The bedroom features a bed dressed in a vibrant patterned cover with orange, grey, and white tones. Two lamps on each side provide soft illumination. A floral artwork hangs above the bed, and a neutral grey wall creates a calm backdrop.

Condo in Lincoln Square

4.97 out of 5 average rating, 412 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. My partner and I 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!

Superhost

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 Lake View

4.99 out of 5 average rating, 637 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.

Superhost

A living room displays a large, vibrant artwork featuring a beach scene, complemented by a modern flat-screen TV mounted on the wall. Natural light filters through two windows with wooden blinds, casting soft shadows on the floor, which is adorned with a decorative area rug.

Condo in West Town

4.97 out of 5 average rating, 807 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.