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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.

  • Modern Chicago Loft with a Complimentary Garage Spot
    PlusEntire apartment · 2 guests · 1 bed · 1 bath
    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.”

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

  • LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
    SUPERHOSTEntire apartment · 3 guests · 2 beds · 1 bath
    LUX 1BR/1BA Top-Floor Unobstructed Downtown Views

    AIRBNB SUPERHOST W/ OVER 600 REVIEWS (PLEASE SEE OTHER LISTINGS) Better views than any hotel! Top-floor, high-rise Apt above the clouds in the heart of Downtown blocks from Michigan Ave (Magnificent Mile), Navy Pier, The Bean, & ALL of Downtown's Top Hotels, Bars, & Restaurants. RIVER NORTH/STREETERVILLE/GOLD COAST considered one of safest & most beautiful in Chicago Condo over 800 sq. ft feat. Luxury Jr. 1 bedroom, open space & unique character. 3rd guest has twin daybed in living area.

    What guests are saying:

    “Super easy access and the view was great! Stylish and chic decor. Margarita responded to my texts quickly as I had a few questions—very pleasant. I made a few recommendations on updates for future guests!”

Vacation 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 vacation rentals

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

Other great vacation rentals in Chicago

LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Private room
LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Price:$67 CAD/night
Modern Chicago Loft with a Complimentary Garage Spot
PlusEntire apartment
Modern Chicago Loft with a Complimentary Garage Spot
Price:$69 CAD/night
Charming Small Minimalist Designer Loft,Blue Line
Entire apartment
Charming Small Minimalist Designer Loft,Blue Line
Price:$55 CAD/night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$135 CAD/night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:$34 CAD/night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:$19 CAD/night
Sunny Logan Square Bedroom
Private room
Sunny Logan Square Bedroom
Price:$36 CAD/night
J2.Next to Downtown!By bus to go straight Downtown
Private room
J2.Next to Downtown!By bus to go straight Downtown
Price:$28 CAD/night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$96 CAD/night
Elegant south loop 2 bedroom apt, parking, WiFi
Entire apartment
Elegant south loop 2 bedroom apt, parking, WiFi
Price:$51 CAD/night
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Entire apartment
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Price:$43 CAD/night
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Private room
SAFE CENTRAL LOCATION CLEAN APARTMENT FREE PARKING
Price:$61 CAD/night
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