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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
    SUPERHOSTEntire 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:

    “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 bath
    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.”

  • Enjoy Chicago’s Nightlife from Studio Apartment
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Enjoy Chicago’s Nightlife from Studio Apartment

    Keep updated on work demands at a vintage-style wooden desk in the working corner of this gorgeous studio apartment. The combination of metals, velvet and wood in the interior make this a beautiful apartment and a contemporary dream. 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:

    “I love staying at Nala and Owen studio! It felt very homey I definitely love the little details like the plants and the paintings on the walls! I think the giraffe was my favorite! My whole stay was wonderful! I couldn’t have asked for a better experience! The day of my check out I had left my plant I got throughout my trip and Nala made everything possible so that I could get my plant back! Super grateful for that! Highly recommend the studio”

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

Other great vacation rentals in Chicago

Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:ﺩ.ﺇ150 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:ﺩ.ﺇ505 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:ﺩ.ﺇ269 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:ﺩ.ﺇ54 / night
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
SUPERHOSTEntire loft
Luxury Chicago Loft, 1 blk to train w/ 2 pkg spots
Price:ﺩ.ﺇ444 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:ﺩ.ﺇ556 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:ﺩ.ﺇ149 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:ﺩ.ﺇ312 / night
Chicago chinatown great location(B) (中文房东)
SUPERHOSTPrivate room
Chicago chinatown great location(B) (中文房东)
Price:ﺩ.ﺇ143 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:ﺩ.ﺇ177 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:ﺩ.ﺇ367 / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:ﺩ.ﺇ130 / night
Show all

Learn more about Chicago

What types of vacation rentals are available in Chicago?

Here in Chicago, there are plenty of options for places to stay. Here are a few examples:
  • Apartments (4,696 rentals)
  • Houses (1,150 rentals)
  • Guest suites (242 rentals)

Are there apartments with WiFi?

Who doesn’t want WiFi in their apartment? Here in Chicago, you’ll find 4,531 apartments that have WiFi.

What area should I stay in when traveling to Chicago?

Every area of Chicago is unique. So where should you stay? Let the locals help you decide. These are their top recommendations:
  • Lakeview (418 rentals)
  • Logan Square (340 rentals)
  • River North (325 rentals)
  • Loop (306 rentals)
  • Lincoln Park (258 rentals)

What are the top attractions in Chicago?

Locals agree that these attractions are worth a visit:
  • The Art Institute of Chicago (363 rentals)
  • Lincoln Park (138 rentals)
  • Wrigley Field (750 rentals)
  • Navy Pier (99 rentals)
  • Field Museum of Natural History (144 rentals)

What are some kid-friendly activities in Chicago?

Locals agree—these are all great places to take the kids:
  • Lincoln Park
  • Wrigley Field
  • Shedd Aquarium
  • Field Museum of Natural History
  • Museum of Science and Industry

What are the top places to eat in Chicago?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • Big Star
  • Longman & Eagle
  • Revolution Brewing
  • Parson's Chicken & Fish
  • Au Cheval