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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 flat · 4 guests · 2 beds · 1 bathroom
    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:

    “I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

  • 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:

    “This place was perfect for my boyfriend and I on our 2 night stop in Chicago! It’s super stylish and cozy, and the bed is super comfortable. We visited the main sights in Chicago by bike - it was the perfect location!”

  • Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bathroom
    Enjoy city & lake views from this suite w/ shared pool, gym, sauna, & basketball

    The health and safety of our guests, homeowners, and employees is our number one priority. Many of our vacation rentals minimize person-to-person contact with private amenities and entry via smart locks or lockboxes. Plus, each reservation is backed by 24/7 customer support and expert cleaning in line with current CDC guidelines.

    What guests are saying:

    “I can't say enough about this place. Check in with the doorman was nice and easy, which is something that can start your trip off on a positive or negative note. My goodness, the view from this apartment is incredible! It's really something being able to see the Willis Tower right outside your windows (both the living room and bedroom). As far as location goes, it is perfect. You are able to walk to most major attractions in downtown Chicago, as well as a variety of restaurants and bars. The location is extremely convenient, and I didn't even uber once while I was there! Another thing I loved were the amenities. It was really nice having a washer/dryer to use, as well as a 24 hr gym so that I could work off that delicious Chicago Deep Dish pizza! I highly recommend this place and would definitely stay here again!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:£35 / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:£28 / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:£79 / night
Eclectic and Colorful Retro Apartment near Logan Square
SUPERHOSTEntire flat
Eclectic and Colorful Retro Apartment near Logan Square
Price:£77 / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:£69 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire flat
Basement Studio w/Free St. Parking, Humboldt Park
Price:£36 / night
Attic cozy guests suite near South Loop in Chicago
SUPERHOSTEntire guest suite
Attic cozy guests suite near South Loop in Chicago
Price:£67 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:£133 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire flat
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:£37 / night
Unwind in the Bath at a Hip, Historic Coach House
SUPERHOSTEntire guest house
Unwind in the Bath at a Hip, Historic Coach House
Price:£80 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire flat
Enjoy Chicago’s Nightlife from Studio Apartment
Price:£48 / night
Happy home to share
Private room
Happy home to share
Price:£48 / night
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