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Vacation rental apartments in Chicago

Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated apartments in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Modern Chicago Loft with a Complimentary Garage Spot
PLUSEntire 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:

“The place was super clean. Literally the cleanest airbnb I’ve ever stayed at. Super easy to check in and out. The hosts were also easy to get in contact with and they made sure to check in to see if everything was fine after we arrived. Would definitely stay again!”

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.”

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bath
Stylish, Cozy Apartment for the Perfect Get Away

This amazing apartment is located in the Little Village community in Chicago. Little Village is the heart of the Mexican community because it's vivid representation of the Mexican culture. In addition, the apartment is close to two Chicago parks where you can enjoy a walk or a bike ride.

What guests are saying:

“Paul’s place was beautiful! My husband and I loved the neighborhood, and had a wonderful stay. Everything was exceptional. Can’t wait to stay again next time we return to Chicago! We miss our feline friend Abu already!”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular apartment amenities in Chicago

  • Wifi
  • Kitchen
  • Air conditioning
  • Free parking
  • Heating

Houses in Chicago

Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:GYD7,360 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:GYD6,257 / night
Self check in self checkout near downtown Chicago
Private room
Self check in self checkout near downtown Chicago
Price:GYD7,300 / night
#4 Historic Chicago Home - Private Single Bedroom
SUPERHOSTPrivate room
#4 Historic Chicago Home - Private Single Bedroom
Price:GYD7,538 / night
Cozy room in a Charming Coach House
SUPERHOSTPrivate room
Cozy room in a Charming Coach House
Price:GYD8,343 / night
warm comfortable home with lots to offer
SUPERHOSTPrivate room
warm comfortable home with lots to offer
Price:GYD6,109 / night
Happy home to share
Private room
Happy home to share
Price:GYD12,514 / night
ENTIRE CITY ROW HOUSE  WITH 2 CAR PARKING & YARD
SUPERHOSTEntire house
ENTIRE CITY ROW HOUSE WITH 2 CAR PARKING & YARD
Price:GYD16,775 / night
5min walk to UnivOfChgo. MODERN Luxe
Private room
5min walk to UnivOfChgo. MODERN Luxe
Price:GYD6,674 / night
Garden Level King and 2 Twin Beds. OUTDOOR HOT TUB
SUPERHOSTPrivate room
Garden Level King and 2 Twin Beds. OUTDOOR HOT TUB
Price:GYD12,097 / night
Cozy Home and Garden
SUPERHOSTEntire house
Cozy Home and Garden
Price:GYD12,514 / night
Super Cozy Bed/Bath in Awesome Andersonville Home!
SUPERHOSTPrivate room
Super Cozy Bed/Bath in Awesome Andersonville Home!
Price:GYD9,385 / night
Show all

Pet-friendly apartments

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:GYD31,285 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:GYD17,997 / night
Cozy Private Coach House
SUPERHOSTEntire apartment
Cozy Private Coach House
Price:GYD12,812 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:GYD38,228 / night
Chicago Modern Studio in High Rise building
Entire apartment
Chicago Modern Studio in High Rise building
Price:GYD10,428 / night
Checkerboard Studio with Private Outdoor Hot Tub and Yard
PLUSEntire apartment
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Price:GYD30,361 / night
Palos Hills Apartment with a View
SUPERHOSTEntire apartment
Palos Hills Apartment with a View
Price:GYD18,652 / night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire apartment
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:GYD39,210 / night
Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Price:GYD20,051 / night
Ukrainian Village Garden Retreat
Entire apartment
Ukrainian Village Garden Retreat
Price:GYD17,882 / night
Great Place Garfield Park 3 Bedroom
SUPERHOSTEntire apartment
Great Place Garfield Park 3 Bedroom
Price:GYD9,237 / night
The Hobbit Hole
SUPERHOSTEntire apartment
The Hobbit Hole
Price:GYD10,428 / night
Show all

Apartments with WiFi

Modern Chicago Loft with a Complimentary Garage Spot
PLUSEntire apartment
Modern Chicago Loft with a Complimentary Garage Spot
Price:GYD15,790 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:GYD12,812 / night
Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:GYD3,068 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PLUSEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:GYD11,025 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:GYD31,285 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:GYD26,100 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:GYD10,428 / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:GYD12,395 / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:GYD10,785 / night
Cozy Private Coach House
SUPERHOSTEntire apartment
Cozy Private Coach House
Price:GYD12,812 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:GYD17,997 / night
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
SUPERHOSTEntire apartment
Cozy, New Luxury 2 Bedroom 15 Mins to O'Hare
Price:GYD10,249 / 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