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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.

  • 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.”

  • 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.”

  • Walk to Lake Michigan From a Contemporary Uptown Haven
    PlusEntire apartment · 2 guests · 1 bed · 1 bath
    Walk to Lake Michigan From a Contemporary Uptown Haven

    Awaken in a comfy queen size bed, ready to explore nearby attractions. Everything needed is readily at hand in this cozy space. Start the day with a quick breakfast in a compact kitchen, then refresh under a rain shower in a gleaming white bathroom. Please note that this unit is located above a late night bar, which may add to the charm of it for some but may also pose to be a noise nuisance for light sleepers. We encourage you to read the reviews of past guests to make an informed decision.

    What guests are saying:

    “Me and my best friend came for a short stay during this pandemic and it was an amazing getaway. We felt right at home. The apartment was warm and cozy. It had everything a girl could need to stay in all day and binge watch shows and of course drink lol. We loved that the host was so thoughtful with providing essential things like make up remover and clean towels. Definitely will be coming back for another perfect getaway ☺️🥰”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
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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:€45 / night
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Private room
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Price:€32 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:€13 / night
J2.Next to Downtown!By bus to go straight Downtown
Private room
J2.Next to Downtown!By bus to go straight Downtown
Price:€18 / night
Charming Small Minimalist Designer Loft,Blue Line
Entire apartment
Charming Small Minimalist Designer Loft,Blue Line
Price:€36 / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:€23 / night
Abby's 2720 2F
Private room
Abby's 2720 2F
Price:€20 / night
Sunny Logan Square Bedroom
Private room
Sunny Logan Square Bedroom
Price:€23 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PlusEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:€36 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:€63 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:€88 / night
CLEAN STYLISH LOFT +$0 PARKING IN DOWNTOWN CHICAGO
Private room
CLEAN STYLISH LOFT +$0 PARKING IN DOWNTOWN CHICAGO
Price:€32 / night
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