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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.

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!”

Room with private bathroom
Private room · 1 guest · 1 bath
Room with private bathroom

The unit is near Blue Line Train station,young people after work pubs, Supermarkets. and restaurants.

What guests are saying:

“Rebecca is a very kind, sweet and thoughtful hostess. I was able to meet her in person because my daughter and I were 4 hours early upon checking in. She graciously welcomed us in. She also gave us tips on the local restaurants and the best way to get around Chicago. I would definitely stay here again!”

Chicago Modern Studio in High Rise building
Entire apartment · 2 guests · 1 bed · 1 bath
Chicago Modern Studio in High Rise building

Awesome studio in High rise building on the 10 floor, Secured building with pool and great view, safe area , laundry on same floor, My place is close to Johnnie's Beef, Massa Cafe Italiano, Felony Franks, and Russell's Barbecue. My place is good for couples, solo adventurers, business travelers, and small furry friends (pets).

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

Self check in self checkout near downtown Chicago
Private room
Self check in self checkout near downtown Chicago
Price:GYD6,698 / night
Your Fantastic Futon! 1st Floor TV room with locks
SUPERHOSTPrivate room
Your Fantastic Futon! 1st Floor TV room with locks
Price:GYD4,814 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:GYD6,280 / night
Studio space w/ private bathroom near midway
SUPERHOSTPrivate room
Studio space w/ private bathroom near midway
Price:GYD7,387 / night
warm comfortable home with lots to offer
SUPERHOSTPrivate room
warm comfortable home with lots to offer
Price:GYD6,070 / night
Catmandu
SUPERHOSTPrivate room
Catmandu
Price:GYD10,556 / night
Private Room with single bed in comfortabe Home
SUPERHOSTPrivate room
Private Room with single bed in comfortabe Home
Price:GYD6,070 / night
Garden Level King and 2 Twin Beds. OUTDOOR HOT TUB
SUPERHOSTPrivate room
Garden Level King and 2 Twin Beds. OUTDOOR HOT TUB
Price:GYD12,141 / night
Private bedroom A in a quiet Chicago suburb.
SUPERHOSTPrivate room
Private bedroom A in a quiet Chicago suburb.
Price:GYD6,908 / night
Aquarius house,safe Blue Line, upscale
SUPERHOSTPrivate room
Aquarius house,safe Blue Line, upscale
Price:GYD15,699 / night
Super Cozy Bed/Bath in Awesome Andersonville Home!
SUPERHOSTPrivate room
Super Cozy Bed/Bath in Awesome Andersonville Home!
Price:GYD9,419 / night
Cozy room in a Charming Coach House
SUPERHOSTPrivate room
Cozy room in a Charming Coach House
Price:GYD7,835 / night
Show all

Pet-friendly apartments

Chicago Modern Studio in High Rise building
Entire apartment
Chicago Modern Studio in High Rise building
Price:GYD10,466 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:GYD30,500 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:GYD18,360 / night
Heart of Wicker Park Bright 1st Story Walk-Up!
SUPERHOSTPrivate room
Heart of Wicker Park Bright 1st Story Walk-Up!
Price:GYD6,399 / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:GYD20,394 / night
Ukrainian Village Garden Retreat
Entire apartment
Ukrainian Village Garden Retreat
Price:GYD18,240 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:GYD37,768 / night
PANORAMIC SKYLINE VIEWS At Your Luxury Studio Loft
SUPERHOSTEntire apartment
PANORAMIC SKYLINE VIEWS At Your Luxury Studio Loft
Price:GYD19,615 / night
Palos Hills Apartment with a View
SUPERHOSTEntire apartment
Palos Hills Apartment with a View
Price:GYD18,749 / night
Spacious Bedroom w/ private Bathroom (Loyola area)
SUPERHOSTPrivate room
Spacious Bedroom w/ private Bathroom (Loyola area)
Price:GYD8,373 / night
The Hobbit Hole
SUPERHOSTEntire apartment
The Hobbit Hole
Price:GYD10,765 / night
Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Price:GYD20,243 / night
Show all

Apartments with WiFi

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:GYD3,021 / night
Room with private bathroom
Private room
Room with private bathroom
Price:GYD4,605 / night
Chicago Modern Studio in High Rise building
Entire apartment
Chicago Modern Studio in High Rise building
Price:GYD10,466 / night
Small Sleeper sofa in eclectic living room.
SUPERHOSTShared room
Small Sleeper sofa in eclectic living room.
Price:GYD5,652 / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:GYD10,018 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:GYD10,466 / night
Explore Chicago from an Urban Sanctuary with Free Parking
PLUSEntire apartment
Explore Chicago from an Urban Sanctuary with Free Parking
Price:GYD14,353 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:GYD30,500 / night
Cozy and Stylish Studio with Free Parking in Irving Park
PLUSEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:GYD11,661 / night
Metropolitan En Suite with Exceptional Loop Access
SUPERHOSTPrivate room
Metropolitan En Suite with Exceptional Loop Access
Price:GYD12,499 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PLUSEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:GYD11,661 / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:GYD4,186 / 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