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Vacation rentals in Chicago

Vacation rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

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

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bathroom
Stylish, Cozy Apartment for the Perfect Get Away

This amazing apartment is located in the Little Village community in Chicago. Little Village is the heart of the Mexican community because it's vivid representation of the Mexican culture. In addition, the apartment is close to two Chicago parks where you can enjoy a walk or a bike ride.

What guests are saying:

“Paul’s place was beautiful! My husband and I loved the neighborhood, and had a wonderful stay. Everything was exceptional. Can’t wait to stay again next time we return to Chicago! We miss our feline friend Abu already!”

Room with private bathroom
Private room · 1 guest · 1 bathroom
Room with private bathroom

The unit is near Blue Line Train station,young people after work pubs, Supermarkets. and restaurants.

What guests are saying:

“Rebecca is a very kind, sweet and thoughtful hostess. I was able to meet her in person because my daughter and I were 4 hours early upon checking in. She graciously welcomed us in. She also gave us tips on the local restaurants and the best way to get around Chicago. I would definitely stay here again!”

Your Fantastic Futon! 1st Floor TV room with locks
SUPERHOSTPrivate room · 1 guest · 1 bed · 2.5 shared bathrooms
Your Fantastic Futon! 1st Floor TV room with locks

The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gatherings of any kind. We're in the heart of the Rogers Park neighborhood, walking distance from many restaurants & 1 block from Loyola Beach Park. Breakfast is self-serve & included in the cost of the room. In the kitchen you will find bagels, cream cheese, eggs, yogurt, cereal & fresh fruit. The home is run by friendly local folks who are happy to help during your stay.

What guests are saying:

“Privacy of a hotel, amenities and personal touch of a bnb, and the international clientele and socialization of a hostel. Cozy, clean, and better equipped than one could ever anticipate, you'll need for nothing here. Everybody is extremely kind and helpful and full of interesting stories, to boot! I can't wait to come back”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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  • Unique stays

Popular amenities for Chicago holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chicago

Self check in self checkout near downtown Chicago
Private room
Self check in self checkout near downtown Chicago
Price:₹2,391 / night
Chicago Modern Studio in High Rise building
Entire flat
Chicago Modern Studio in High Rise building
Price:₹3,736 / night
Small Sleeper sofa in eclectic living room.
SUPERHOSTShared room
Small Sleeper sofa in eclectic living room.
Price:₹2,018 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat
Hip Chicago Apartment - FREE Parking Spot Included
Price:₹4,591 / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:₹2,637 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:₹3,042 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire flat
Cosmopolitan nest in Oak Parks North Side
Price:₹3,736 / night
Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:₹3,577 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:₹2,242 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire flat
Best in Chicago, private, amazing garden space
Price:₹10,889 / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:₹1,495 / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:₹4,462 / night
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