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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.

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
SUPERHOST
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.

Pilsen Remodeled Studio Rental
Entire apartment · 2 guests · 1 bed · 1 bath

Pilsen Remodeled Studio RentalHello! Studio with full kitchen, updated appliances, tall ceilings, central air and heating, garbage disposal, double door fridge, and newly replaced front door. Entire apartment recently refurbished, pet friendly. On 18th Street, near Thalia Hall, walking distance of restaurants etc., bus stop is in front of building, walking distance from pink line, close to downtown.

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:R470 ZAR / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:R457 ZAR / night
The Maywood Manor: Shared Room 5, Bed 2 (Queen)
SUPERHOSTShared room
The Maywood Manor: Shared Room 5, Bed 2 (Queen)
Price:R381 ZAR / night
Cozy Home and Garden
SUPERHOSTEntire house
Cozy Home and Garden
Price:R914 ZAR / night
Cozy Room with Free Street Parking
SUPERHOSTPrivate room
Cozy Room with Free Street Parking
Price:R655 ZAR / night
Room for solo traveler near midway airport suite B
SUPERHOSTPrivate room
Room for solo traveler near midway airport suite B
Price:R365 ZAR / night
Your Fantastic Futon! 1st Floor TV room with locks
Private room
Your Fantastic Futon! 1st Floor TV room with locks
Price:R350 ZAR / night
Hidden Gem w/private Bath. Walk to Univ/hospital
Private room
Hidden Gem w/private Bath. Walk to Univ/hospital
Price:R609 ZAR / night
10 min to downtown chicago, mccormick & chinatown
SUPERHOSTPrivate room
10 min to downtown chicago, mccormick & chinatown
Price:R485 ZAR / night
Amazing, spacious, bright Garden Suite
Entire house
Amazing, spacious, bright Garden Suite
Price:R1,066 ZAR / night
Great Affordable Room in Chicago Lincoln Square
Private room
Great Affordable Room in Chicago Lincoln Square
Price:R472 ZAR / night
5min walk to UnivOfChgo. MODERN Luxe
Private room
5min walk to UnivOfChgo. MODERN Luxe
Price:R548 ZAR / 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:R1,431 ZAR / night
Simple&Suite 2 - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Simple&Suite 2 - Clean & Private Retreat, Pets OK
Price:R1,142 ZAR / night
Aunt Linda's Apartment with a View in Palos
SUPERHOSTEntire apartment
Aunt Linda's Apartment with a View in Palos
Price:R1,355 ZAR / night
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
SUPERHOSTPrivate room
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
Price:R685 ZAR / night
The Hobbit Hole
Entire apartment
The Hobbit Hole
Price:R761 ZAR / night
Humboldt Hide Away
SUPERHOSTEntire apartment
Humboldt Hide Away
Price:R1,294 ZAR / night
Stylish & Urban - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Stylish & Urban - Clean & Private Retreat, Pets OK
Price:R1,703 ZAR / night
The Mid Century - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
The Mid Century - Clean & Private Retreat, Pets OK
Price:R1,703 ZAR / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:R1,294 ZAR / night
Village Cottage - Clean & Private Retreat
SUPERHOSTEntire apartment
Village Cottage - Clean & Private Retreat
Price:R1,381 ZAR / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:R1,457 ZAR / night
Cozy modern artsy top floor apartment
Entire apartment
Cozy modern artsy top floor apartment
Price:R777 ZAR / night

Apartments with WiFi

Stylish & Ample 1PBR STAYCATION SPACE For You
SUPERHOSTPrivate room
Stylish & Ample 1PBR STAYCATION SPACE For You
Price:R529 ZAR / night
Cozy Downtown Apartment with perfect location 5
SUPERHOSTEntire apartment
Cozy Downtown Apartment with perfect location 5
Price:R1,501 ZAR / night
MODERN LOFT Downtown by McCormick w/KING BED WiFi
SUPERHOSTEntire apartment
MODERN LOFT Downtown by McCormick w/KING BED WiFi
Price:R305 ZAR / night
A cozy room for solo travelers | Mins to the Loop
SUPERHOSTPrivate room
A cozy room for solo travelers | Mins to the Loop
Price:R579 ZAR / night
Hattie’s House
Private room
Hattie’s House
Price:R533 ZAR / night
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Price:R305 ZAR / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:R455 ZAR / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:R827 ZAR / night
Private room, shared apartment, easy city access.
SUPERHOSTPrivate room
Private room, shared apartment, easy city access.
Price:R624 ZAR / night
Luxury City Center Loft on a Traffic-free Street
Private room
Luxury City Center Loft on a Traffic-free Street
Price:R389 ZAR / night
Wicker Park: Newly-Furnished Nest Close To It All!
Private room
Wicker Park: Newly-Furnished Nest Close To It All!
Price:R563 ZAR / night
Calming Edgewater Glen Sanctuary
Entire apartment
Calming Edgewater Glen Sanctuary
Price:R1,238 ZAR / night

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