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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
    PlusEntire 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.”

  • 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:

    “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.”

  • Spacious Serene En Suite, Incredible Loop Location
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Spacious Serene En Suite, Incredible Loop Location

    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 many tourist and conference destinations including McCormick Place (many are 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:

    “Anne was extremely helpful and hospitable. Any question or clarification we had was quickly responded to. This was one of the best equipped Airbnb’s I’ve been at, she had everything a guest could need. The apartment is kept very clean. The area is nice—walking distance from grocery stores, restaurants, and not even 15 minutes away from downtown. It was a great stay!”

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

Holiday rentals under £114

The average cost for a stay in Chicago is £142/night.

Modern Chicago Loft with a Complimentary Garage Spot
PlusEntire flat
Modern Chicago Loft with a Complimentary Garage Spot
Price:£41 / night
Sonder | Coeval | Lovely 1BR + Balcony
Entire flat
Sonder | Coeval | Lovely 1BR + Balcony
Price:£51 / night
Enjoy Chicago’s Nightlife from Studio Apartment
PlusEntire flat
Enjoy Chicago’s Nightlife from Studio Apartment
Price:£33 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat
Hip Chicago Apartment - FREE Parking Spot Included
Price:£41 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:£72 / night
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
SUPERHOSTEntire flat
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
Price:£24 / night
Charming Small Minimalist Designer Loft,Blue Line
Entire flat
Charming Small Minimalist Designer Loft,Blue Line
Price:£24 / night
LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Private room
LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Price:£40 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:£11 / night
Sunny Logan Square Bedroom
Private room
Sunny Logan Square Bedroom
Price:£21 / night
Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOSTEntire loft
Lakeview Loft-Vintage Chicago, Modern Amenities
Price:£56 / night
Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:£40 / night
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