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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.

  • 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.”

  • Modern Chicago Loft with a Complimentary Garage Spot
    PlusEntire 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:

    “WOW. Look no further for an amazing place to stay. As soon as I pulled up to the building I was blown away at how beautiful the neighborhood was. The building itself is extremely secure and makes you feel safe even coming in and out since there are security cameras. There is a tattoo shop, and Mexican food restaurant attached to the building which makes it easy to not have to leave your room. The air bnb itself is GORGEOUS, and all of my friends who live in the city noted it was bigger than their studio apartments. The furniture is all high end designer, the bed was ridiculously comfortable, and it had plenty of extra furniture making it to where you could potentially have up to 5-6 guest comfortably over for dinner or a game. Thankfully the kitchen had everything I needed as well, including saving my dinner with some flour. I can't wait to book this place again, I actually cried leaving because I enjoyed my stay so much.”

  • Logan Square Lookout
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Logan Square Lookout

    Great top floor apartment along a tree lined street with free street parking. Has a cozy small bedroom with a spacious living room and kitchen. On Site Coin operated laundry. Great back yard with garden area. This is in the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So I'm always nearby.

    What guests are saying:

    “Patricks place felt like a home away from home! Super cozy and quiet. He was very responsive to messages. Parking was easy to find. Bathroom was stocked with shampoo, conditioner, body wash, toothpaste, q-tips, and more. Will definitely be staying again in the future!”

Holiday rentals for every style

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  • Homes
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Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:$71 AUD / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$142 AUD / night
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
SUPERHOSTEntire apartment
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
Price:$81 AUD / night
Cozy place close to downtown Chicago!
SUPERHOSTEntire apartment
Cozy place close to downtown Chicago!
Price:$22 AUD / 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:$109 AUD / night
Enjoy Chicago’s Nightlife from Studio Apartment
PlusEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$73 AUD / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$123 AUD / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:$58 AUD / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:$29 AUD / night
Best in Chicago, private, excellent work space
SUPERHOSTEntire apartment
Best in Chicago, private, excellent work space
Price:$181 AUD / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:$71 AUD / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:$145 AUD / night
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