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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 Studio Apt in the Heart of Wicker Park!
Entire rental unit · 2 guests · 1 bed · 1 bath
Private Studio Apt in the Heart of Wicker Park!*No Hidden Cleaning Fees or Deposits* Enjoy Wicker Park with your own private renovated studio apartment! This large renovated studio is on the corner of Wood St & Le Moyne St. The apartment comes complete with a large living space, pull out couch bed, kitchenette with fridge & microwave, air conditioning, wifi, TV, new bathroom, laundry facilities, and a communal rooftop deck with skyline views. Close to EL train, highway, shopping, restaurants, nightlife, cafes, 606 bike trail and more!
Lovely two bedroom near Chicago, IL.
Entire rental unit · 7 guests · 2 beds · 1 bath
Lovely two bedroom near Chicago, IL.A quiet, clean, peaceful two bedroom apartment near Chicago gives you the experience of the city with the safety of a suburb - just 20 minutes from all the attractions downtown. This lovely garden unit is located just ten minutes from midway airport, minutes away from parks, public transportation, shopping centers and many great restaurants as well.
City View near Downtown Chicago Sox & Chinatown
SUPERHOST
Private room · 1 guest · 1 bed · 1 shared bath
City View near Downtown Chicago Sox & ChinatownClean, cozy and private. Recently renovated, enjoy the comfort of staying on a brand new place. Features include central AC and heating with air humidifier, high speed internet, all amenities listed and essentials. Centralized location close to downtown Chicago, Chinatown, White Sox, Pilsen, South Loop & McCormick Convention Center.

Vacation rentals for every style

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Houses in Chicago

  1. Private room
  2. Near West Side
B4 - Chicago Next to Downtown - Private Room
SUPERHOST
  1. Private room
  2. McKinley Park
P03 New Queen Bed near Downtown Chicago
SUPERHOST
  1. Private room
  2. McKinley Park
p09 Downtown Chicago 8 minutes away SELF CHECK IN
  1. Private room
  2. Woodlawn
Perfect Oasis 4mins walk to University & hospital
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
  1. Private room
  2. Bridgeport
R2 Prime New House Perfect for your stay
  1. Private room
  2. Rogers Park
Your Fantastic Futon! 1st Floor TV room with locks
  1. Private room
  2. Bridgeport
L2 Private bedroom in Bridgeport near Downtown
  1. Shared room
  2. Calumet Heights
B. MANSION SHARED COED ROOM (NOT PRIVATE) TOP BUNK
  1. Private room
  2. Little Italy/UIC
Private room in apartment in FANTASTIC location
SUPERHOST
  1. Private room
  2. Austin
Little Farm in the City Back Bedroom
  1. Private room
  2. Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital

Pet-friendly apartments

  1. Entire rental unit
  2. Irving Park
Cozy Studio Apartment
SUPERHOST
  1. Entire rental unit
  2. West Town/Noble Square
Great location. Free parking.
  1. Entire rental unit
  2. Logan Square
Perfect Cozy Logan Spot (Free Parking & Fast WiFi)
  1. Entire rental unit
  2. South Loop/Printers Row
*Luxury High Rise, Clean Design/Balcony/Amenities!
  1. Entire rental unit
  2. Austin
Suburb feel with city convenience
  1. Entire rental unit
  2. Logan Square
The Secret Stache
SUPERHOST
  1. Entire rental unit
  2. Bridgeport
Stylish and Cozy newly renovated Bridgeport Apt
  1. Private room
  2. Humboldt Park
Convenient location!
  1. Entire rental unit
  2. Lincoln Square
The Hobbit Hole
  1. Entire rental unit
  2. West Town/Noble Square
New Spot in West Town
  1. Entire rental unit
  2. West Town/Noble Square
New Spot in West Town pt.2!
SUPERHOST
  1. Entire rental unit
  2. West Town/Noble Square
Fully Furnished Apartment Wicker Park Free Parking

Apartments with WiFi

SUPERHOST
  1. Private room
  2. Armour Square
New Queen bed near Downtown Chicago Chinatown
  1. Entire rental unit
  2. Lakeview
Spacious Studio, Amazing Location!
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Bright Private Room in Wicker Park
  1. Private room
  2. McKinley Park
Cozy Private Bedroom w/ Queen Bed & 5min to Metro
SUPERHOST
  1. Entire rental unit
  2. Lakeview
Stylish, posh, and very private flat (1)
SUPERHOST
  1. Private room
  2. Near North Side
★ DOWNTOWN CHICAGO ★ Interactive Art Room
SUPERHOST
  1. Private room
  2. Albany Park
Cozy guest room in sunny, expansive garden flat
  1. Entire rental unit
  2. Bridgeport
1 Bedroom Apartment by McCormick Place & Chinatown
  1. Entire rental unit
  2. River West
Cute Designer Touch Minimal Loft,Blue Line
  1. Entire rental unit
  2. Woodlawn
Deluxe Modern 2BR Apt 4min walk to UofC & Hospital
  1. Private room
  2. McKinley Park
Single Bedroom w/ Twin Bed & 5min to Metro
SUPERHOST
  1. Private room
  2. Wicker Park
Spacious & Attractive Private Room in Wicker Park