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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.

  • Hip Chicago Apartment - FREE Parking Spot Included
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    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.”

  • 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.”

  • G1. Best location and most affordable! So much fun
    SUPERHOSTPrivate room · 1 guest · 1 bed · 1 shared bath
    G1. Best location and most affordable! So much fun

    Everybody is welcome! The location is just awesome! There is a bunch of restaurants and brunch places within 0.5miles all walkable. We are literally next to downtown, only 15-20minutes to the heart of Downtown by car or public trans. There’s a blue line train station 8min walk. Train works 24/7, goes straight to downtown and O’Hare airport too. One of the safest neighborhoods in Chicago also Wicker Park is one mile away. free parking on the street. We provide all the amenities you might need.

    What guests are saying:

    “A great place to crash for the night if you are on a budget. Parking was free nearby and the place was accessible to the local public transit. Josana was super friendly and helped us during check in. The room was also super clean.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chicago vacation rentals

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

Vacation rentals under $140

The average cost for a stay in Chicago is $175/night.

Modern Chicago Loft with a Complimentary Garage Spot
PlusEntire apartment
Modern Chicago Loft with a Complimentary Garage Spot
Price:$50 / night
Sonder | Coeval | Lovely 1BR + Balcony
Entire apartment
Sonder | Coeval | Lovely 1BR + Balcony
Price:$63 / night
PRIVATE COZY FLOOR 5MIN TO DOWNTOWN + FREE PARKING
Private room
PRIVATE COZY FLOOR 5MIN TO DOWNTOWN + FREE PARKING
Price:$35 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$88 / night
Enjoy Chicago’s Nightlife from Studio Apartment
PlusEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$40 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$50 / night
Charming Small Minimalist Designer Loft,Blue Line
Entire apartment
Charming Small Minimalist Designer Loft,Blue Line
Price:$30 / night
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Entire apartment
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Price:$27 / night
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
SUPERHOSTEntire apartment
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
Price:$30 / night
J2.Next to Downtown!By bus to go straight Downtown
Private room
J2.Next to Downtown!By bus to go straight Downtown
Price:$20 / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:$25 / night
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
SUPERHOSTEntire apartment
Sunny 1 BDR w/plants - Foodie Paradise - Logan Sq
Price:$72 / night
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