Skip to content

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.

Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOST
Entire apartment · 2 guests · 2 beds · 1 bath

Basement Studio w/Free St. Parking, Humboldt ParkLocated in Humboldt Park, 6 miles from downtown, this basement studio is perfect for a stay in Chicago. We are located on a strip with approximately 11 houses and no houses across. There is a lot of Park area. At night it's a quiet neighborhood. We are located half a block away from the bus to Navy Pier, approx. 45 minutes to get to Navy Pier. There is free street parking available with NO parking permit required. There is a pool (only in summer) and park access half a block away.

Casa de Sueño/Private Bathroom/Near Train/Loyola
Private room · 2 guests · 2 beds · 1 private bath

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge flat screen TV with Apple TV with free Netflix, you can Stream movies/shows through your Apple device or use one of these converter apps to stream from android: https://letsview.com/mirror-android-to-apple-tv.html Also has an Amazon Firestick and HDMI hookup. Iron/board, closet w/ hangers, sharper image radio/speakers/cd player, basic office supplies. Printer in LR. Free parking with permits (ask).

Great location. Free parking.  One night available
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1 bath

Great location. Free parking. One night availableGreat 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.

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

  1. Private room
  2. Chicago
Bucktown - Private Room
ﺩ.ﺇ154 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
ﺩ.ﺇ184 per night
SUPERHOST
  1. Entire house
  2. Chicago
Private Andersonville Guest Suite
ﺩ.ﺇ442 per night
SUPERHOST
  1. Private room
  2. Chicago
Logan Square Vintage Deluxe Private Suite & Bath
ﺩ.ﺇ265 per night
SUPERHOST
  1. Private room
  2. Chicago
Private Bed and Bathroom in a Great Location
ﺩ.ﺇ246 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
ﺩ.ﺇ185 per night
  1. Entire house
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
ﺩ.ﺇ367 per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
ﺩ.ﺇ127 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
ﺩ.ﺇ147 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
ﺩ.ﺇ107 per night
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking
ﺩ.ﺇ129 per night
  1. Entire house
  2. Chicago
Newly Renovated 2br, 1 ba- Logan Square
ﺩ.ﺇ359 per night

Pet-friendly apartments

SUPERHOST
  1. Entire apartment
  2. Chicago
Susie's Sanctuary- Pet friendly +parking
ﺩ.ﺇ437 per night
  1. Entire apartment
  2. Chicago
Trendy Wicker Park with parking, sleeps up to 5
ﺩ.ﺇ475 per night
  1. Entire apartment
  2. Forest Park
Cute 1 bedroom near Blue line
ﺩ.ﺇ231 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
ﺩ.ﺇ250 per night
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
ﺩ.ﺇ331 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
ﺩ.ﺇ336 per night
PLUS
  1. Entire apartment
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
ﺩ.ﺇ455 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Discover Chicago from a Modern Apartment
ﺩ.ﺇ484 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
❤️ Cozy and Comfy 1BR Condo in Logan Square!
ﺩ.ﺇ341 per night
  1. Entire apartment
  2. Chicago
New Spot in West Town
ﺩ.ﺇ263 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Entire 1st Floor Apt near O'Hare/ORD & Blue Line
ﺩ.ﺇ349 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ukrainian Village Garden Retreat
ﺩ.ﺇ347 per night

Apartments with WiFi

SUPERHOST
  1. Entire apartment
  2. Chicago
A laid-back studio few minutes from Wrigley Field
ﺩ.ﺇ323 per night
  1. Private room
  2. Chicago
Hattie’s House
ﺩ.ﺇ129 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Apartment close to Midway and Downtown! 1bdr, 1bth
ﺩ.ﺇ202 per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
ﺩ.ﺇ81 per night
PLUS
  1. Entire apartment
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
ﺩ.ﺇ310 per night
SUPERHOST
  1. Private room
  2. Chicago
Private Bedroom Near O’hare in Norwood Park
ﺩ.ﺇ96 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Chicago Sanctuary: Perfect 1BD in West Town!
ﺩ.ﺇ195 per night
PLUS
  1. Entire apartment
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
ﺩ.ﺇ336 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Edgewater, private, charming coach house 1 ( of 2)
ﺩ.ﺇ434 per night
  1. Entire apartment
  2. Chicago
Discover North Side Chicago from Modern Studio APT
ﺩ.ﺇ272 per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary
ﺩ.ﺇ298 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious Apartment minutes from Downtown/McCormick
ﺩ.ﺇ192 per night

Nearby destinations