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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.

Modern Chicago Loft with a Complimentary Garage Spot
PLUSEntire flat · 2 guests · 1 bed · 1 bathroom
Modern Chicago Loft with a Complimentary Garage Spot

Dine by the natural wood breakfast bar or on the rooftop deck. This classy loft boasts open-plan living, exposed brickwork and stunning artwork. Check out our other available listings within the same building by clicking below on our host profile.

What guests are saying:

“The place was super clean. Literally the cleanest airbnb I’ve ever stayed at. Super easy to check in and out. The hosts were also easy to get in contact with and they made sure to check in to see if everything was fine after we arrived. Would definitely stay again!”

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!”

Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

What guests are saying:

“I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

Walk to Lake Michigan From a Contemporary Uptown Haven
PLUSEntire flat
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$ 68 SGD / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$ 194 SGD / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire flat
Best in Chicago, private, amazing garden space
Price:$ 205 SGD / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:$ 81 SGD / night
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
SUPERHOSTEntire loft
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
Price:$ 184 SGD / night
Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOSTEntire loft
Lakeview Loft-Vintage Chicago, Modern Amenities
Price:$ 116 SGD / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:$ 57 SGD / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:$ 116 SGD / night
Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:$ 71 SGD / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:$ 48 SGD / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:$ 128 SGD / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:$ 129 SGD / night
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