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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.”

  • Metropolitan En Suite with Exceptional Loop Access
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Metropolitan En Suite with Exceptional Loop Access

    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 tourist- and conference-friendly destinations including McCormick Place (many 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:

    “The apartment was super well located, right in downtown Chicago. We were at a walking distance to all tourist points of interest. The bedroom was very comfortable, as was the bathroom. All the apartment was very clean. I never saw Anne, but her instructions were very clear for check in and check out, as well as for entering and leaving the apartment. I would definitely stay there again on some other trip to Chicago.”

  • Walk to Lake Michigan From a Contemporary Uptown Haven
    PlusEntire flat · 2 guests · 1 bed · 1 bathroom
    Walk to Lake Michigan From a Contemporary Uptown Haven

    Awaken in a comfy queen size bed, ready to explore nearby attractions. Everything needed is readily at hand in this cozy space. Start the day with a quick breakfast in a compact kitchen, then refresh under a rain shower in a gleaming white bathroom. Please note that this unit is located above a late night bar, which may add to the charm of it for some but may also pose to be a noise nuisance for light sleepers. We encourage you to read the reviews of past guests to make an informed decision.

    What guests are saying:

    “Me and my best friend came for a short stay during this pandemic and it was an amazing getaway. We felt right at home. The apartment was warm and cozy. It had everything a girl could need to stay in all day and binge watch shows and of course drink lol. We loved that the host was so thoughtful with providing essential things like make up remover and clean towels. Definitely will be coming back for another perfect getaway ☺️🥰”

Holiday 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 holiday rentals

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

Other great holiday rentals in Chicago

Modern Chicago Loft with a Complimentary Garage Spot
PlusEntire flat
Modern Chicago Loft with a Complimentary Garage Spot
Price:₹3,759 / night
Sunny Logan Square Bedroom
Private room
Sunny Logan Square Bedroom
Price:₹1,955 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:₹1,052 / night
LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Private room
LARGE MASTER SUITE, PRIVATE BATHROOM, FREE PARKING
Price:₹3,684 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PlusEntire flat
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:₹3,007 / night
J2.Next to Downtown!By bus to go straight Downtown
Private room
J2.Next to Downtown!By bus to go straight Downtown
Price:₹1,504 / night
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
SUPERHOSTEntire flat
GROCERY STORE DOWNSTAIRS | KING SIZE BED | BALCONY
Price:₹2,331 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat
Hip Chicago Apartment - FREE Parking Spot Included
Price:₹5,262 / night
Spacious Serene En Suite, Incredible Loop Location
SUPERHOSTPrivate room
Spacious Serene En Suite, Incredible Loop Location
Price:₹3,684 / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:₹1,879 / night
5min walk to UnivOfChicago. MODERN LUXE
Private room
5min walk to UnivOfChicago. MODERN LUXE
Price:₹2,255 / night
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Entire flat
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
Price:₹1,955 / night
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