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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.

  • Modern Chicago Loft with a Complimentary Garage Spot
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    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.”

  • Adorable Studio by McKinley Park. Newly Remodeled!
    Entire flat · 2 guests · 1 bed · 1 bathroom
    Adorable Studio by McKinley Park. Newly Remodeled!

    My place is close to Target, La Palapa Sea Food, CTA trains, CTA buses, McKinley Park. You’ll love my place because of the coziness and decor. New remodel!. My place is good for couples, solo adventurers, and business travelers. We do have a pup that lives on the property but he is usually in the front yard and has never been in the rental apartment!

    What guests are saying:

    “We enjoyed our stay, would definitely come back. Had everything we needed including coffee pot and microwave. Good WiFi. Easy access to buses and the orange line. 24 hour diner at the corner. Slept well - comfortable bed, no sounds from upstairs, only a bit of road noise but easy to cancel out with a white noise app on my phone. Everything was very clean and well kept. We had a fun weekend, CAC river cruise, Second City, and a taping of Wait Wait Don't Tell Me, recommend it all.”

  • 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.

  • Homes
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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

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:€12 / night
Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:€40 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:€114 / night
Unwind in a Charming Apartment with Skylights
SUPERHOSTEntire flat
Unwind in a Charming Apartment with Skylights
Price:€62 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire flat
Enjoy Chicago’s Nightlife from Studio Apartment
Price:€62 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:€36 / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:€77 / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:€76 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire flat
Cosmopolitan nest in Oak Parks North Side
Price:€41 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire flat
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:€41 / night
Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOSTEntire loft
Lakeview Loft-Vintage Chicago, Modern Amenities
Price:€61 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat
Hip Chicago Apartment - FREE Parking Spot Included
Price:€80 / night
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