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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!”

  • 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:

    “I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

  • Walk to Lake Michigan From a Contemporary Uptown Haven
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    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:

    “This was a nice little studio. It was clean and there were daily necessities like toilet paper, shampoo, etc., provided. I stayed with my partner for a week and we used everything the studio provided. The lights were a soft white color which gave it a cozy feeling and the air conditioner always kept the room cool. If you live a simple, quiet lifestyle this is a great place to stay and would highly recommend!”

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:R756 ZAR / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:R823 ZAR / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:R1,344 ZAR / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:R672 ZAR / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:R773 ZAR / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:R2,520 ZAR / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:R1,428 ZAR / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:R588 ZAR / 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:R2,100 ZAR / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:R235 ZAR / night
Contemporary Oak Park Loft
SUPERHOSTEntire loft
Contemporary Oak Park Loft
Price:R914 ZAR / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:R756 ZAR / 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