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, 118 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

Condo in Evanston

4.97 out of 5 average rating, 117 reviews

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Harmony of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

Superhost

A spacious rooftop deck features artificial grass, offering a comfortable area for relaxation. A dining table with chairs is present, alongside two folding chairs for additional seating. The skyline is visible in the distance, enhancing the outdoor setting.

Condo in Chicago

4.89 out of 5 average rating, 128 reviews

Luxury Wicker Park Penthouse w/ Private Rooftop

Welcome to my Wicker Park condo! The current photos don’t do it justice. This spacious 2 BR/2 Bath has high ceilings, a newly built huge private rooftop deck, indoor garage space, master bath w jacuzzi, fireplace, washer/dryer, dishwasher, & central air. Come stay in a peaceful, quiet place while still being just a 3 min walk from great food, bars, coffee shops, shopping & green space. 6 min walk to the Damen EL. (Blue line, same as O'Hare airport, and 5 stops from the loop).

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, 244 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 spacious living area features high ceilings and large windows, allowing natural light to fill the room. A wooden dining table is accompanied by several chairs, while a sleek kitchen is visible in the background, highlighted by modern appliances and cabinetry.

Condo in Chicago

4.78 out of 5 average rating, 226 reviews

Modern Luxury In Old Town - Sleeps 4

Stay in one of the best neighborhoods in Chicago - Old Town! Recently renovated spacious top floor condo with all modern amenities, in a classic 19th century Chicago home in one of the best parts of the city with access to dining, bars, entertainment and more. Ideal for traveling families and friends, and plenty of Chicago culture nearby, from nearly every era. A neighborhood bar with Frank Sinatra's favorite ribs! Michelin-starred restaurants!

Superhost

The four-story brick building is shown from an angled view, highlighting large arched windows and a blue awning. A blue sign reading '747 LOFTS' is prominent, and the surrounding area features pedestrian-friendly sidewalks and greenery.

Condo in Chicago

4.86 out of 5 average rating, 119 reviews

Cabin 308 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.

Guest favorite

Condo in Oak Park

4.94 out of 5 average rating, 246 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, 641 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 workspace area is showcased with a stylish glass desk and a woven chair. A lamp stands on the desk, providing light, while a round mirror hangs on the wall behind it. Textured stone and wooden floors add warmth to the space.

Condo in Chicago

4.87 out of 5 average rating, 241 reviews

A Stones Throw from U Chicago South Campus!

This 2 bedroom garden unit located in vintage World's Columbian Exposition era building, it's been renovated and updated. You can't get much closer to the University of Chicago campus. This quiet garden unit is within walking distance of lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.

Guest favorite

The brick building features a modern facade with large windows allowing for ample natural light. A well-maintained garden area is enclosed by a black iron fence. The entrance is marked by a stylish door with contemporary lighting fixtures on either side.

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.

Guest favorite

A brick two-story apartment building is situated among well-maintained greenery. Large windows are visible on the front facade, allowing natural light to enter. The residential neighborhood features a mix of similarly styled homes, highlighting the inviting character of the area.

Condo in Berwyn

4.9 out of 5 average rating, 127 reviews

Picturesque Apartment in Berwyn

This stylish place to stay is perfect for group trips. 2 bedrooms with queen beds, spacious living room with a sofa bed and well equipped kitchen. The apartment is located in North Berwyn, 15 minutes drive from Downtown Chicago, walking distance to Roosevelt Road's bars and restaurants, 0.8 miles to CTA Blue Line rail line station.