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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:

    “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!”

  • 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:

    “It was nice, stylish, and clean! Unbeatable price! Parking spot was an added bonus! Neighbors can be a bit too loud if you’re trying to find some peace and quiet.”

  • Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
    SUPERHOSTEntire loft · 4 guests · 2 beds · 2 bathrooms
    Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots

    Luxury Wrigleyville loft in one of the best areas of Chicago. ONE block from public transportation that can take you to the downtown area. Very safe neighborhood that has families and fun. Experience Chicago like a local.

    What guests are saying:

    “Awesome spot! We stayed with 3 adults and it was very comfortable. The area is really safe and the parking spot in the back is super convenient! We were close to public transportation though we ended up not needing to use it since the parking spot allowed us to drive around the city easily. We were within walking distance to many restaurants. We cooked a few meals in the apartment and the kitchen had everything we needed for pots and utensils, etc. As noted in the description, it is a 3rd floor walk-up so keep that in mind if you have anyone traveling with you that may struggle with that (we didn't have any issue with climbing the stairs at all, so if you're in good health, it's not a problem). I think the price is really great for the area. I did a ton of research before booking our trip to Chicago and this place is definitely a great deal!! Communication was great and effortless! Highly recommended!”

Holiday rentals for every style

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  • Homes
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Popular amenities for Chicago holiday rentals

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

Other great holiday rentals in Chicago

Best in Chicago, private, amazing garden space
SUPERHOSTEntire flat
Best in Chicago, private, amazing garden space
Price:₹10,045 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire flat
Enjoy Chicago’s Nightlife from Studio Apartment
Price:₹3,720 / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire flat
Stunning Retro Apartment in Andersonville
Price:₹5,357 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire flat
Basement Studio w/Free St. Parking, Humboldt Park
Price:₹3,348 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:₹8,036 / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire flat
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:₹11,384 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:₹7,441 / night
Eclectic and Colorful Retro Apartment near Logan Square
SUPERHOSTEntire flat
Eclectic and Colorful Retro Apartment near Logan Square
Price:₹7,143 / 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:₹7,366 / night
Bright, Modern Apartment in a Vintage Greystone
SUPERHOSTEntire flat
Bright, Modern Apartment in a Vintage Greystone
Price:₹9,301 / night
Private Room in Bridgeport Home
SUPERHOSTPrivate room
Private Room in Bridgeport Home
Price:₹4,836 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire flat
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:₹3,423 / night
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