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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, 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.

Cosmopolitan nest in Oak Parks North Side
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Cosmopolitan nest in Oak Parks North SideWhether visiting Oak Park's historic district or exploring the Windy City for the renowned museums and its nightlife, we welcome you into our home. You are guaranteed a peaceful stay in your own apartment with private entrance on the first floor in our single family home. We are a professional family who maintain a quiet residence. CTA public transportation just steps away.

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
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Cozy Home and Garden
SUPERHOSTEntire house
Cozy Home and Garden
Cozy Room with Free Street Parking
SUPERHOSTPrivate room
Cozy Room with Free Street Parking
Room for solo traveler near midway airport suite B
SUPERHOSTPrivate room
Room for solo traveler near midway airport suite B
The Maywood Manor: Room 4 (Twin Bed, 1 Guest)
SUPERHOSTPrivate room
The Maywood Manor: Room 4 (Twin Bed, 1 Guest)
Your Fantastic Futon! 1st Floor TV room with locks
Private room
Your Fantastic Futon! 1st Floor TV room with locks
Hidden Gem w/private Bath. Walk to Univ/hospital
Private room
Hidden Gem w/private Bath. Walk to Univ/hospital
10 min to downtown chicago, mccormick & chinatown
SUPERHOSTPrivate room
10 min to downtown chicago, mccormick & chinatown
Great Affordable Room in Chicago Lincoln Square
Private room
Great Affordable Room in Chicago Lincoln Square
5min walk to UnivOfChgo. MODERN Luxe
Private room
5min walk to UnivOfChgo. MODERN Luxe
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Pet-friendly apartments

Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Simple&Suite 2 - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Simple&Suite 2 - Clean & Private Retreat, Pets OK
Aunt Linda's Apartment with a View in Palos
SUPERHOSTEntire apartment
Aunt Linda's Apartment with a View in Palos
Hip & Spacious Garden Studio near Logan Square!
Entire apartment
Hip & Spacious Garden Studio near Logan Square!
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
SUPERHOSTPrivate room
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
The Hobbit Hole
Entire apartment
The Hobbit Hole
Humboldt Hide Away
SUPERHOSTEntire apartment
Humboldt Hide Away
Andersonville Living
SUPERHOSTEntire apartment
Andersonville Living
Great location.
SUPERHOSTEntire apartment
Great location.
Village Cottage - Clean & Private Retreat
SUPERHOSTEntire apartment
Village Cottage - Clean & Private Retreat
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
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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
Chicago luxury studio with splendid city view
Entire apartment
Chicago luxury studio with splendid city view
Hattie’s House
Private room
Hattie’s House
Cozy guest room 1 block from U of C
SUPERHOSTPrivate room
Cozy guest room 1 block from U of C
Cozy and Stylish Studio with Free Parking in Irving Park
PLUSEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Private room, shared apartment, easy city access.
SUPERHOSTPrivate room
Private room, shared apartment, easy city access.
Spacious & Charming Private Room in Wicker Park
SUPERHOSTPrivate room
Spacious & Charming Private Room in Wicker Park
Wicker Park: Newly-Furnished Nest Close To It All!
Private room
Wicker Park: Newly-Furnished Nest Close To It All!
Chicago chinatown great location(B) (中文房东)
SUPERHOSTPrivate room
Chicago chinatown great location(B) (中文房东)
Vintage 3BR Apartment in Logan Square
SUPERHOSTEntire apartment
Vintage 3BR Apartment in Logan Square
Large vintage inspired room in the heart of Logan
SUPERHOSTPrivate room
Large vintage inspired room in the heart of Logan
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Nearby destinations