Skip to content
Sign up
Log in
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!”

  • 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.”

  • Queen Room in River North Boutique Hotel
    SUPERHOSTHotel room · 2 guests · 1 bed · 1 bathroom
    Queen Room in River North Boutique Hotel

    My place is close to Magnificent Mile, Water Tower Place, Museum of Contemporary Art, Signature Lounge, Signature Room At the 95th.. You’ll love my place because of the ambiance. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

    What guests are saying:

    “You can expect a clean room and well-maintained building. The building was quiet during my stay, which was helpful in getting a quality night’s sleep. Despite being located near elevated train tracks, I barely recognized the sound of trains speeding by. FieldHouse Jones is in an ideal location. It is near the Mag Mile, Gold Coast, Old Town, and a quick drive to Lincoln Park. Overall, I enjoyed my stay. I recommend anyone visiting Chicago who loves sports or trendy, modern spaces to consider booking a stay at FieldHouse Jones!”

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

Other great holiday rentals in Chicago

Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:₹2,625 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:₹1,050 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat
Hip Chicago Apartment - FREE Parking Spot Included
Price:₹5,250 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire flat
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:₹11,099 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:₹6,000 / night
Logan Square Lookout
SUPERHOSTEntire flat
Logan Square Lookout
Price:₹3,375 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire flat
Enjoy Chicago’s Nightlife from Studio Apartment
Price:₹3,750 / night
Sonder | Essex on the Park | Ideal 1BR + Pool
Entire flat
Sonder | Essex on the Park | Ideal 1BR + Pool
Price:₹12,074 / night
Great location.
SUPERHOSTEntire flat
Great location.
Price:₹6,374 / night
Lakeview Loft-Vintage Chicago, Modern Amenities
SUPERHOSTEntire loft
Lakeview Loft-Vintage Chicago, Modern Amenities
Price:₹5,175 / night
Hattie’s House
Private room
Hattie’s House
Price:₹2,625 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire flat
Cosmopolitan nest in Oak Parks North Side
Price:₹3,450 / night
Show all