
Condo vacation rentals in Cook County
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Top-rated condo rentals in Cook County
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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.
4.98 out of 5 average rating, 167 reviews
Apartment in Clarendon Hills.
Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.
5.0 out of 5 average rating, 136 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.
4.93 out of 5 average rating, 281 reviews
Charming Condo near U.C./Loop/McCormick Place
Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.
4.81 out of 5 average rating, 219 reviews
Can't Beat This 2min Walk to Wrigley!
My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!
4.81 out of 5 average rating, 287 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.
4.95 out of 5 average rating, 171 reviews
Spacious 4 Bedroom Condo
Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.
4.95 out of 5 average rating, 217 reviews
Modern Chicago Movie Themed Apt
Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!
4.88 out of 5 average rating, 229 reviews
Chicago River West 4 Bedroom / 3 Bathroom
Two-level River West home great for travelers who want to see the best of Chicago (its neighborhoods!). The living room is a converted store front, so you benefit from airy ceilings and tons of natural light, which carries into the kitchen - between that and the new appliances, cooking here is a blast. The 4 bedrooms and 3 bathrooms are spread out over both floors, so it's ideal for families and groups of friends - book today!
4.82 out of 5 average rating, 258 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.
4.96 out of 5 average rating, 119 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.
4.93 out of 5 average rating, 354 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.
4.91 out of 5 average rating, 346 reviewsPopular amenities for Cook County condo rentals
Weekly condo rentals

Stunning Wicker-Park Flat with Parking!
5.0 out of 5 average rating, 182 reviews
Welcoming 2BR in Chicago's Best Neighborhood!
4.85 out of 5 average rating, 362 reviews
Wrigleyville Inn. Historic Greystone, Free Parking
4.99 out of 5 average rating, 125 reviews
Renovated 3br Duplex In Logan Square W/parking
4.81 out of 5 average rating, 324 reviews
CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
4.93 out of 5 average rating, 225 reviews
East Lakeview Designer Condo with 2 Bd, 2 Bath
4.96 out of 5 average rating, 161 reviews
Susie's Space. 2BR easy parking & pet friendly
4.92 out of 5 average rating, 393 reviews
💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
4.99 out of 5 average rating, 147 reviewsPet-friendly condo rentals

Ukrainian Village 3BR/3BA • Private Patio, Parking
4.98 out of 5 average rating, 125 reviews
Spacious 5-BR Apt next to transit Free Parking
4.88 out of 5 average rating, 118 reviews
Luxuriously bright 6-bedroom duplex: The Treehouse
4.93 out of 5 average rating, 164 reviews
Large Remodeled Home in Lincoln Park, Sleeps 12!
4.97 out of 5 average rating, 148 reviews
Convenient & Spacious 3BR Condo w/Free Parking
4.9 out of 5 average rating, 160 reviews
Spacious 3BR Near McCormick Place + Transit
4.95 out of 5 average rating, 171 reviews
Spacious Evanston Unit - Walk to Northwestern U
4.78 out of 5 average rating, 721 reviews
1,800ft² Parking Workspace W/D Full Kitch
4.99 out of 5 average rating, 221 reviewsCondo rentals with a pool

Just remodeled apartment close to airport and mall
4.92 out of 5 average rating, 124 reviews
Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
4.96 out of 5 average rating, 146 reviews
2 bed/2 bath with skyline views
5.0 out of 5 average rating, 9 reviews
Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
4.82 out of 5 average rating, 71 reviews
Red Door
5.0 out of 5 average rating, 9 reviews
Best view and luxury style, Located in Downtown

Lovely 2 Bed 2 Bathroom!

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
4.96 out of 5 average rating, 139 reviewsDestinations to explore
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