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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.

Private room, shared apartment, easy city access
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bath

Private room, shared apartment, easy city accessThis 2 story home is too much space for us, so we chose to run the 2nd floor over to Airbnb. This is an affordable way for folks to visit Chicago and for us to meet interesting people. Edgewater is a beautiful, quiet, safe northside neighborhood with beaches, theaters, grocery, shopping, restaurants, lake access, bike paths, and Loyola University. Heading downtown? The CTA Red Line is just a 7 minute walk. Be downtown in 40 minutes. Have a car? Street parking is always available.

Chicago Chinatown great location(A)(中文房东)
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bath

Chicago Chinatown great location(A)(中文房东)My apartment is located in the center of Chinatown, surrounded by Starbucks, supermarkets, banks, and food from all over China. The traffic is very convenient and there is a subway (7 minutes from the red and blue lines)

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

Stylish, Shared Apartment for the Perfect Get AwayThis 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.

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
  • Guesthouses

Popular apartment amenities in Chicago

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

Houses in Chicago

Self check in self checkout near downtown Chicago
SUPERHOSTPrivate room
Self check in self checkout near downtown Chicago
Price:GYD7,304 / night
Perfect Oasis 4mins walk to University & hospital
Private room
Perfect Oasis 4mins walk to University & hospital
Price:GYD6,678 / night
Prime Brand New House Perfect for your stay R2
Private room
Prime Brand New House Perfect for your stay R2
Price:GYD6,261 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:GYD6,261 / night
Room for solo traveler near midway airport suite B
SUPERHOSTPrivate room
Room for solo traveler near midway airport suite B
Price:GYD5,009 / night
Your Fantastic Futon! 1st Floor TV room with locks
Private room
Your Fantastic Futon! 1st Floor TV room with locks
Price:GYD4,800 / night
The Blue Room
SUPERHOSTPrivate room
The Blue Room
Price:GYD7,096 / night
Elegant, Bright Flat
Entire house
Elegant, Bright Flat
Price:GYD14,609 / night
Cozy room in a Charming Coach House
SUPERHOSTPrivate room
Cozy room in a Charming Coach House
Price:GYD7,453 / night
Affordable Luxury 9 min to downtown chicago
SUPERHOSTPrivate room
Affordable Luxury 9 min to downtown chicago
Price:GYD6,440 / night
Great Affordable Room in Chicago Lincoln Square
Private room
Great Affordable Room in Chicago Lincoln Square
Price:GYD6,470 / night
Edgewater Arts & Crafts Retreat
Private room
Edgewater Arts & Crafts Retreat
Price:GYD6,887 / night

Pet-friendly apartments

Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Price:GYD19,618 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:GYD21,913 / night
Sophisticated, 2-BR Luxury Condo in Old Town
Entire apartment
Sophisticated, 2-BR Luxury Condo in Old Town
Price:GYD18,868 / night
Simple&Suite 2 - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Simple&Suite 2 - Clean & Private Retreat, Pets OK
Price:GYD15,652 / night
Cozy Studio Apartment
Entire apartment
Cozy Studio Apartment
Price:GYD9,690 / night
Aunt Linda's Apartment with a View in Palos
SUPERHOSTEntire apartment
Aunt Linda's Apartment with a View in Palos
Price:GYD18,574 / night
Casa de Sueño/Private Bathroom/Near Train/Loyola
SUPERHOSTPrivate room
Casa de Sueño/Private Bathroom/Near Train/Loyola
Price:GYD7,734 / night
Humboldt Hide Away
SUPERHOSTEntire apartment
Humboldt Hide Away
Price:GYD17,739 / night
The Hobbit Hole
SUPERHOSTEntire apartment
The Hobbit Hole
Price:GYD10,435 / night
The Mid Century - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
The Mid Century - Clean & Private Retreat, Pets OK
Price:GYD23,345 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:GYD17,739 / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:GYD19,887 / night

Apartments with WiFi

A cozy room for solo travelers | Mins to the Loop
SUPERHOSTPrivate room
A cozy room for solo travelers | Mins to the Loop
Price:GYD7,931 / night
Spacious, light-drenched studio-private entrance!
SUPERHOSTEntire apartment
Spacious, light-drenched studio-private entrance!
Price:GYD16,487 / night
Hattie’s House
Private room
Hattie’s House
Price:GYD7,304 / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:GYD4,174 / night
Private Studio
Entire apartment
Private Studio
Price:GYD7,812 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:GYD10,852 / night
Spacious & Charming Private Room in Wicker Park
SUPERHOSTPrivate room
Spacious & Charming Private Room in Wicker Park
Price:GYD6,351 / night
Luxury City Center Loft on a Traffic-free Street
Private room
Luxury City Center Loft on a Traffic-free Street
Price:GYD5,009 / night
Bridgeport Garden Apartment
SUPERHOSTEntire apartment
Bridgeport Garden Apartment
Price:GYD16,249 / night
Chicago chinatown great location(B) (中文房东)
SUPERHOSTPrivate room
Chicago chinatown great location(B) (中文房东)
Price:GYD8,139 / night
Do Chicago Right! 1B/1B in Luxe Amenities Building
SUPERHOSTEntire apartment
Do Chicago Right! 1B/1B in Luxe Amenities Building
Price:GYD16,487 / night
Large vintage inspired room in the heart of Logan
SUPERHOSTPrivate room
Large vintage inspired room in the heart of Logan
Price:GYD9,391 / night

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