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Vacation rentals in Cook County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cook County

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

Superhost
Apartment in Chicago
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.
$119 per night
Superhost
Guest suite in Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.
$87 per night
Superhost
Home in Chicago
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
$99 per night

Other great vacation rentals in Cook County

Superhost
Apartment in Chicago
Explore Chicago from an Urban Sanctuary with Free Parking
$59 per night
Superhost
Apartment in Oak Park
Cosmopolitan Nest in Oak Park North Side
$70 per night
Superhost
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
$129 per night
Superhost
Apartment in Chicago
Private Studio Apt in the Heart of Wicker Park!
$76 per night
Superhost
Apartment in Chicago
Studio, Steps from Wrigley Field
$85 per night
Superhost
Apartment in Chicago
Hip Chicago Apartment - FREE Parking Spot Included
$64 per night
Superhost
Apartment in Chicago
Lovely Andersonville Apt with Ideal Location
$93 per night
Superhost
Apartment in Chicago
Stunning Retro Apartment in Andersonville
$120 per night
Superhost
Apartment in Chicago
☀️Amazing Gold Coast Apt w/ Rooftop Pool & Gym☀️
$116 per night
Superhost
Guesthouse in Chicago
Entire private coach house near transit, nightlife
$108 per night
Superhost
Apartment in Oak Park
Chic Retreat in Historic Victorian House-Free PKG
$116 per night
Superhost
Cottage in Merrillville
The Hideaway
$80 per night

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