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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.

  • Industrial Style Chicago Loft with FREE parking
    SUPERHOSTEntire loft · 2 guests · 1 bed · 1 bathroom
    Industrial Style Chicago Loft with FREE parking

    Enjoy Chicago in this beautifully renovated one bedroom loft with a chic, industrial vibe. Drink your morning coffee on the private outdoor deck or sleep in late on the California king sized bed. The loft’s lovely art deco ceiling, exposed brick walls and free Netflix are just some of the great features you’ll love. Free parking is included and you’ll be just a 10 minute drive from catching a game at Wrigley Field as well as a 15-20 minute drive to the airport and main downtown attractions.

    What guests are saying:

    “The place was fine, it was easy to find, the parking was nice, and it was within walking distance to a few stores and markets still open during this time. The pictures are pretty accurate, and the back porch was by-far the best part. The whole place could have benefitted from some personal touches such as a blanket for the couch, or a kitchen towel, or some hooks on the back of the bathroom door to hang towels. Overall, it was a fine stay.”

  • 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:

    “Apartment was clean and comfortable. Free parking spot in the back was a plus. I mainly chose this place since it was less expensive than most Chicago Airbnb’s, however I didn’t realize how far it would actually be from downtown. 20 minute walk to Logan Square train station then a 15-20 minute ride to downtown. I would recommend this place if you don’t necessarily care about being super close to downtown. Overall, I was pleased with my stay but wasn’t prepared for the commute.”

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

Holiday rentals for every style

Get the amount of space that is right for you.

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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

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:£60 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:£78 / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire flat
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:£118 / night
Best in Chicago, private, excellent work space
SUPERHOSTEntire flat
Best in Chicago, private, excellent work space
Price:£99 / night
Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:£36 / night
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
SUPERHOSTEntire flat
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
Price:£45 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:£79 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PlusEntire flat
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:£40 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:£32 / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:£68 / night
Stunning Retro Apartment in Andersonville
PlusEntire flat
Stunning Retro Apartment in Andersonville
Price:£50 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire flat
Basement Studio w/Free St. Parking, Humboldt Park
Price:£36 / night
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