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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.

Cozy guest room 1 block from U of C
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bath

Cozy guest room 1 block from U of CCozy guest room with office desk and futon. Kitchen and living room are available for guest(s) to use. 1 block from University of Chicago, 15 minutes from downtown, 2 blocks from Metra, 4 blocks from Lake Shore Drive and CTA Green Line train. Nearby historic Hyde Park area. Grocery store Jewel-Osco is within walking distance. Parking is street parking 1/2 block away from the apartment. Host lives at listing.

From $20 / night
Great location.
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Great location.Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

From $85 / night
Chicago chinatown great location（B） (中文房东）
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bath

Chicago chinatown great location（B） (中文房东）

From $39 / night

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:$29 / night
Little Farm in the City of Chicago, the Green Room
SUPERHOSTPrivate room
Little Farm in the City of Chicago, the Green Room
Price:$60 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:$30 / night
The Maywood Manor: Shared Room 5, Bed 2 (Queen)
SUPERHOSTShared room
The Maywood Manor: Shared Room 5, Bed 2 (Queen)
Price:$25 / night
Cozy Room with Free Street Parking
SUPERHOSTPrivate room
Cozy Room with Free Street Parking
Price:$43 / night
Room for solo traveler near midway airport suite B
SUPERHOSTPrivate room
Room for solo traveler near midway airport suite B
Price:$27 / night
Catmandu 2
SUPERHOSTPrivate room
Catmandu 2
Price:$40 / night
Your Fantastic Futon! 1st Floor TV room with locks
Private room
Your Fantastic Futon! 1st Floor TV room with locks
Price:$23 / night
Hidden Gem w/private Bath. Walk to Univ/hospital
Private room
Hidden Gem w/private Bath. Walk to Univ/hospital
Price:$40 / night
10 min to downtown chicago, mccormick & chinatown
SUPERHOSTPrivate room
10 min to downtown chicago, mccormick & chinatown
Price:$32 / night
5min walk to UnivOfChgo. MODERN Luxe
Private room
5min walk to UnivOfChgo. MODERN Luxe
Price:$36 / night
Bridgeport Prime Location 5min from downtown R1
SUPERHOSTPrivate room
Bridgeport Prime Location 5min from downtown R1
Price:$28 / night
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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
Price:$104 / night
Simple&Suite 2 - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Simple&Suite 2 - Clean & Private Retreat, Pets OK
Price:$75 / night
Aunt Linda's Apartment with a View in Palos
SUPERHOSTEntire apartment
Aunt Linda's Apartment with a View in Palos
Price:$92 / night
Lovely Flat Close to Rush Hospital / United Centre
Private room
Lovely Flat Close to Rush Hospital / United Centre
Price:$25 / night
Elegant 3BR/1BA Apartment Suite
Entire apartment
Elegant 3BR/1BA Apartment Suite
Price:$64 / night
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
SUPERHOSTPrivate room
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
Price:$38 / night
The Hobbit Hole
Entire apartment
The Hobbit Hole
Price:$50 / night
Humboldt Hide Away
SUPERHOSTEntire apartment
Humboldt Hide Away
Price:$86 / night
The Mid Century - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
The Mid Century - Clean & Private Retreat, Pets OK
Price:$112 / night
Stylish & Urban - Clean & Private Retreat, Pets OK
SUPERHOSTEntire apartment
Stylish & Urban - Clean & Private Retreat, Pets OK
Price:$112 / night
Village Cottage - Clean & Private Retreat
SUPERHOSTEntire apartment
Village Cottage - Clean & Private Retreat
Price:$92 / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:$95 / night
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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
Price:$38 / night
Chicago Chinatown great location（A）（中文房东）
SUPERHOSTPrivate room
Chicago Chinatown great location（A）（中文房东）
Price:$49 / night
Hattie’s House
Private room
Hattie’s House
Price:$35 / night
Pilsen Paradise
Entire apartment
Pilsen Paradise
Price:$40 / night
Stylish, Shared Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Shared Apartment for the Perfect Get Away
Price:$16 / night
Cozy and Stylish Studio with Free Parking in Irving Park
PLUSEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:$59 / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:$34 / night
Enjoy Chicago’s Nightlife from Studio Apartment
PLUSEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$47 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:$54 / night
Private room, shared apartment, easy city access.
SUPERHOSTPrivate room
Private room, shared apartment, easy city access.
Price:$41 / night
Bridgeport Garden Apartment
SUPERHOSTEntire apartment
Bridgeport Garden Apartment
Price:$78 / night
Large vintage inspired room in the heart of Logan
SUPERHOSTPrivate room
Large vintage inspired room in the heart of Logan
Price:$45 / night
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Nearby destinations