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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.

Ravenswood Manor, Sleeps 4! Close to El and Parks
SUPERHOST
Entire apartment · 4 guests · 2 beds · 1 bath

Ravenswood Manor, Sleeps 4! Close to El and ParksNewly remodeled one bedroom plus queen sleeper sofa in historic Ravenswood Manor. This unit is on the ground floor of an owner-occupied three-flat on a beautiful tree-lined street with plenty of parking. Close to Brown Line - Francisco Stop - and lots of neighborhood parks. Close to Rockwell and Lincoln Square shopping and restaurants, and next to Albany Park, one of Chicago's most diverse areas. New fixtures, furniture, appliances, free shared laundry, access to backyard upon request.

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

Casa de Sueño/Private Bathroom/Near Train/LoyolaGuests room includes: Queen sized bed, a spacious desk with office supplies, Mini fridge, portable AC IN BR, Blackout curtains, 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 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 on premises
  • Heating

Houses in Chicago

SUPERHOST
  1. Private room
  2. Chicago
m5- Self check in near downtown Chicago
$36 per night
  1. Private room
  2. Chicago
Bucktown - Private Room
$58 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
$51 per night
PLUS
  1. Entire house
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$118 per night
SUPERHOST
  1. Private room
  2. Chicago
Huge Victorian near Loyola, Lake #2
$69 per night
  1. Private room
  2. Chicago
R7 Suite with Private full Bathroom in Bridgeport
$48 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$43 per night
SUPERHOST
  1. Private room
  2. Chicago
p08- Downtown Chicago 8 minutes away New Queen Bed
$42 per night
  1. Private room
  2. Berwyn
Beautiful Bedroom in a nice & safe location.
$30 per night
  1. Private room
  2. Alsip
Safe clean charming close transportation Viva!
$51 per night
SUPERHOST
  1. Private room
  2. Chicago
m1- 9 min to downtown Chicago, 5min to Chinatown
$40 per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
$30 per night

Pet-friendly apartments

SUPERHOST
  1. Entire apartment
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
$98 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Large High-Class Apt Near Beach w/ Free Parking!
$173 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Unwind in a Charming Apartment with Skylights
$129 per night
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$90 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$105 per night
  1. Entire apartment
  2. Chicago
Spacious Vintage Charm North Side Retreat!
$220 per night
  1. Entire apartment
  2. Chicago
Truly Comfy, Elegant Home w/ Garage by Wrigley/CTA
$127 per night
  1. Entire apartment
  2. Chicago
Spacious & bright 2BR Boho-Chic vibe w parking
$104 per night
  1. Entire apartment
  2. Chicago
New Spot in West Town
$80 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ukrainian Village Garden Retreat
$129 per night
  1. Entire apartment
  2. Chicago
Garden apartment in cute Avondale Area
$120 per night
  1. Entire apartment
  2. Chicago
Safe/ EZ Traveling Apt. 2BED/1BATH
$70 per night

Apartments with WiFi

  1. Entire apartment
  2. Chicago
Private, 2BR apt, 6 miles south of Downtwn Chgo
$37 per night
PLUS
  1. Entire apartment
  2. Chicago
Stunning Retro Apartment in Andersonville
$94 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Cozy Bungalow Getaway
$77 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Spacious, light-drenched studio-private entrance!
$83 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Logan Square/Avondale Chic Retreat W/Peloton Bike
$89 per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
$32 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
Basement Studio w/Free St. Parking, Humboldt Park
$58 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Entire City Apartment One block to Train Park Free
$68 per night
  1. Entire apartment
  2. Bellwood
HOME TO U
$48 per night
  1. Entire apartment
  2. Chicago
Cozy Garden Studio in Woodlawn Neighborhood
$57 per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary
$84 per night

Nearby destinations