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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.

Cozy and Stylish Studio with Free Parking in Irving Park
PLUS
Entire rental unit · 2 guests · 1 bed · 1 bath
Cozy and Stylish Studio with Free Parking in Irving ParkWhip up tasty home-cooked meals in this chic, modern condo. Though cozy in size, the open-plan layout maximizes on space. You’ll have everything you need for the duration of your stay including a patio and great local attractions.
Stunning Retro Apartment in Andersonville
PLUS
Entire rental unit · 4 guests · 2 beds · 1 bath
Stunning Retro Apartment in AndersonvilleEscape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full of natural light, the apartment features modern decor and an arty ambiance, making it playful and fun to stay. Free street parking.
Lovely 2-bedroom rental unit
Entire rental unit · 3 guests · 2 beds · 1 bath
Lovely 2-bedroom rental unitKeep it simple at this peaceful and centrally-located place. Just walking distance from beautiful Humboldt park. Just a short 15min drive from downtown Chicago!

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. Willow Springs
Catmandu 2
$40 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$89 per night
SUPERHOST
  1. Private room
  2. Chicago
At the crossroads of comfort and care
$59 per night
  1. Entire residential home
  2. Chicago
CITY HOUSE/FREE PARKING & 3 MIN WALK TO TRAIN
$70 per night
  1. Entire residential home
  2. Franklin Park
Welcoming 1 Bedroom in quiet area, Free parking
$82 per night
SUPERHOST
  1. Entire residential home
  2. Worth
The Comfy King Ranch /King Bed/Fast WiFi/Free Pkg
$215 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
$50 per night
  1. Entire residential home
  2. Elmhurst
Newly Remodeled Furnished Entire House in Elmhurst
$400 per night
  1. Private room
  2. Chicago
Charming Basement with Private Bath- Sleeps 2
$20 per night
SUPERHOST
  1. Private room
  2. Chicago
m5 Self check in near downtown Chicago
$38 per night
SUPERHOST
  1. Private room
  2. Chicago
m6 Self Check in 8 min to downtown Chicago
$42 per night
SUPERHOST
  1. Entire residential home
  2. Chicago
Lincoln Park Cozy 3br Home near Zoo | Lake | Shops
$316 per night

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
$105 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
$89 per night
  1. Entire rental unit
  2. Chicago
Inspiration-themed hideout steps from 606 Trail
$71 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
♥Modern & Chic 3BR | Fireplace+Netflix+Parking♥
$137 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Designer 3BR with Balcony & Elevator on Clark!
$264 per night
  1. Entire rental unit
  2. Berwyn
Lovely 1-bedroom condominium with free designated parking on premises
$69 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
$101 per night
  1. Entire rental unit
  2. Chicago
Lincoln Park / Old Town, Roomy Nook
$146 per night
  1. Entire rental unit
  2. Chicago
Cozy Studio Apartment
$56 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Angie’s Nest
$116 per night
PLUS
  1. Entire rental unit
  2. Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
$109 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Truly Comfy, Elegant Home w/ Garage by Wrigley/CTA
$99 per night

Apartments with WiFi

SUPERHOST
  1. Entire rental unit
  2. Chicago
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
$110 per night
PLUS
  1. Entire rental unit
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
$91 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Vibrant studio close to Andersonville and train
$79 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Royal Coach House Cottage
$105 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
$37 per night
SUPERHOST
  1. Private room
  2. Chicago
★ DOWNTOWN CHICAGO ★
$62 per night
  1. Private room
  2. Chicago
Stylish & Charming 1PBR STAYCATION SPACE For You
$41 per night
PLUS
  1. Entire rental unit
  2. Chicago
Bright, Modern Apartment in a Vintage Greystone
$142 per night
PLUS
  1. Entire rental unit
  2. Chicago
Whole Flat in Private Club. Walk to L, Dining & Shows
$91 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Stylish, posh, and very private flat (1)
$103 per night
PLUS
  1. Entire rental unit
  2. Chicago
King Bed, Huge Spa and Steam Shower, Dining Destination
$120 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Corner heaven 2b/2b w optional parking/sleeps 6
$161 per night