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Vacation rentals in Chicago

Vacation rentals in Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • 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.”

  • 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:

    “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.”

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Chicago vacation rentals

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

Other great vacation rentals in Chicago

Industrial Style Chicago Loft with FREE parking
SUPERHOSTEntire loft
Industrial Style Chicago Loft with FREE parking
Price:$55 CAD/night
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Private room
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Price:$48 CAD/night
J2.Next to Downtown!By bus to go straight Downtown
Private room
J2.Next to Downtown!By bus to go straight Downtown
Price:$28 CAD/night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:$19 CAD/night
Sunny Logan Square Bedroom
Private room
Sunny Logan Square Bedroom
Price:$36 CAD/night
Charming Small Minimalist Designer Loft,Blue Line
Entire apartment
Charming Small Minimalist Designer Loft,Blue Line
Price:$55 CAD/night
Enjoy Chicago’s Nightlife from Studio Apartment
PlusEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$69 CAD/night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$135 CAD/night
Abby's 2720 2F
Private room
Abby's 2720 2F
Price:$31 CAD/night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:$67 CAD/night
Elegant south loop 2 bedroom apt, parking, WiFi
Entire apartment
Elegant south loop 2 bedroom apt, parking, WiFi
Price:$51 CAD/night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$96 CAD/night
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