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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 bath
    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 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:

    “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.”

  • LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
    SUPERHOSTEntire apartment · 3 guests · 2 beds · 1 bath
    LUX 1BR/1BA Top-Floor Unobstructed Downtown Views

    AIRBNB SUPERHOST W/ OVER 600 REVIEWS (PLEASE SEE OTHER LISTINGS) Better views than any hotel! Top-floor, high-rise Apt above the clouds in the heart of Downtown blocks from Michigan Ave (Magnificent Mile), Navy Pier, The Bean, & ALL of Downtown's Top Hotels, Bars, & Restaurants. RIVER NORTH/STREETERVILLE/GOLD COAST considered one of safest & most beautiful in Chicago Condo over 800 sq. ft feat. Luxury Jr. 1 bedroom, open space & unique character. 3rd guest has twin daybed in living area.

    What guests are saying:

    “Super easy access and the view was great! Stylish and chic decor. Margarita responded to my texts quickly as I had a few questions—very pleasant. I made a few recommendations on updates for future guests!”

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

Other great holiday rentals in Chicago

Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:$76 NZD / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:$70 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:$117 NZD / night
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
SUPERHOSTEntire apartment
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
Price:$87 NZD / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:$62 NZD / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:$31 NZD / night
Best in Chicago, private, excellent work space
SUPERHOSTEntire apartment
Best in Chicago, private, excellent work space
Price:$195 NZD / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$133 NZD / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:$22 NZD / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PlusEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$78 NZD / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:$156 NZD / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:$75 NZD / night
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