Skip to content
Sign up
Log in
Vacation rental apartments in Chicago

Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more 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:

    “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.”

  • 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!”

  • Logan Square Lookout
    SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
    Logan Square Lookout

    Great top floor apartment along a tree lined street with free street parking. Has a cozy small bedroom with a spacious living room and kitchen. On Site Coin operated laundry. Great back yard with garden area. This is in the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So I'm always nearby.

    What guests are saying:

    “I stayed at Patrick’s place for about 2 weeks while I was in town for work and the apartment couldn’t have been better! I never had to park more than a block away for parking, there’s a cool bar right on the corner of the block, and it is located only a short drive to pretty much anywhere you would want to go in Chicago. Neighborhood is nice and quiet and neighbors are super friendly. Patrick is also extremely responsive with messages and would check in periodically to ensure that everything was still going smoothly or to see if I needed anything. I can’t recommend this place enough! You’d be hard pressed to find a better location for the value!”

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

Traveler's Dream - 1 bed in a shared bedroom
Hotel room
Traveler's Dream - 1 bed in a shared bedroom
Price:GYD7,702 / night
Queen Room in River North Boutique Hotel
SUPERHOSTHotel room
Queen Room in River North Boutique Hotel
Price:GYD19,285 / night
Shared Artist Loft Own Private Room
SUPERHOSTPrivate room
Shared Artist Loft Own Private Room
Price:GYD21,165 / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:GYD9,403 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:GYD8,477 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:GYD13,434 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:GYD18,209 / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:GYD7,314 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:GYD3,105 / night
Attic cozy guests suite near South Loop in Chicago
SUPERHOSTEntire guest suite
Attic cozy guests suite near South Loop in Chicago
Price:GYD17,761 / night
Eclectic and Colorful Retro Apartment near Logan Square
SUPERHOSTEntire apartment
Eclectic and Colorful Retro Apartment near Logan Square
Price:GYD19,285 / night
Private Room in a Sunny Plant Filled Chicago Condo
SUPERHOSTPrivate room
Private Room in a Sunny Plant Filled Chicago Condo
Price:GYD14,000 / 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