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
$42 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
$50 per night
SUPERHOST
  1. Private room
  2. Chicago
Logan Square Vintage Deluxe Private Suite & Bath
$70 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
$55 per night
SUPERHOST
  1. Entire house
  2. Chicago
MODERN! 2 BD/2 BA RETREAT IN MT. GREENWOOD/BEVERLY
$114 per night
SUPERHOST
  1. Private room
  2. Chicago
Private, Cozy Bedroom Near O’hare in Norwood Park
$32 per night
  1. Entire house
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
$100 per night
SUPERHOST
  1. Private room
  2. Chicago
Self check in near Downtown Chicago
$36 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$41 per night
SUPERHOST
  1. Private room
  2. Oak Park
Antique Filled Home
$65 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
$29 per night
SUPERHOST
  1. Private room
  2. Evanston
A place for scholars & solo adventurers w/parking
$35 per night

Pet-friendly apartments

SUPERHOST
  1. Entire apartment
  2. Chicago
Susie's Sanctuary- Pet friendly +parking
$119 per night
  1. Entire apartment
  2. Chicago
LUXURY 1BR APARTMENT | Wi-Fi | FREE PARKING |
$113 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$78 per night
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$89 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$86 per night
PLUS
  1. Entire apartment
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
$117 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Discover Chicago from a Modern Apartment
$138 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
$85 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
❤️ Cozy and Comfy 1BR Condo in Logan Square!
$97 per night
  1. Entire apartment
  2. Chicago
New Spot in West Town
$71 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ukrainian Village Garden Retreat
$94 per night
  1. Entire apartment
  2. Chicago
Logan Square Historic Getaway
$89 per night

Apartments with WiFi

SUPERHOST
  1. Entire apartment
  2. Chicago
A laid-back studio few minutes from Wrigley Field
$86 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious, light-drenched studio-private entrance!
$81 per night
  1. Private room
  2. Chicago
Hattie’s House
$36 per night
  1. Private room
  2. Chicago
Stylish, Shared Apartment for the Perfect Get Away
$30 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Apartment close to Midway and Downtown! 1bdr, 1bth
$55 per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
$20 per night
PLUS
  1. Entire apartment
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
$99 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Chicago Sanctuary: Perfect 1BD in West Town!
$53 per night
SUPERHOST
  1. Entire apartment
  2. Evanston
Charming studio apartment
$90 per night
SUPERHOST
  1. Entire apartment
  2. Oak Park
Cosmopolitan nest in Oak Parks North Side
$52 per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary
$81 per night
  1. Entire apartment
  2. Chicago
Cool and Comfy First Floor in hoppin' Logan Square
$85 per night

Nearby destinations