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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
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    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:

    “This place was perfect for my boyfriend and I on our 2 night stop in Chicago! It’s super stylish and cozy, and the bed is super comfortable. We visited the main sights in Chicago by bike - it was the perfect location!”

  • Metropolitan En Suite with Exceptional Loop Access
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Metropolitan En Suite with Exceptional Loop Access

    Located in the heart of everything, in a location guests rave about. Enjoy your own private bed/bath en suite in this shared apartment. Easy access to tourist- and conference-friendly destinations including McCormick Place (many within walking distance or a short cab ride), restaurants, all train stops and many buses, both airports, salon/spas, coffee shops, convenience store, independent bookstore, night life, Millenium Park, Navy Pier, gas station, pay parking lot close by, and so much more.

    What guests are saying:

    “The apartment was super well located, right in downtown Chicago. We were at a walking distance to all tourist points of interest. The bedroom was very comfortable, as was the bathroom. All the apartment was very clean. I never saw Anne, but her instructions were very clear for check in and check out, as well as for entering and leaving the apartment. I would definitely stay there again on some other trip to Chicago.”

  • Hip Chicago Apartment - FREE Parking Spot Included
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    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:

    “It was nice, stylish, and clean! Unbeatable price! Parking spot was an added bonus! Neighbors can be a bit too loud if you’re trying to find some peace and quiet.”

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
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chicago

LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$149 NZD / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:$69 NZD / night
Walk to Lake Michigan From a Contemporary Uptown Haven
SUPERHOSTEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$76 NZD / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:$131 NZD / 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:$151 NZD / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$129 NZD / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:$69 NZD / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:$21 NZD / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:$61 NZD / night
Contemporary Oak Park Loft
SUPERHOSTEntire loft
Contemporary Oak Park Loft
Price:$83 NZD / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:$152 NZD / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire apartment
Stunning Retro Apartment in Andersonville
Price:$110 NZD / night
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