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.

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.

From $97 / night
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.

From $84 / night
Great location. Free parking.
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath

Great location. Free parking.Great 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.

From $85 / night

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

  1. Private room
  2. Chicago
m5- Self check in near downtown Chicago
$35 per night
SUPERHOST
  1. Private room
  2. Chicago
Spacious & serene in hip spot. Sleeps 4.
$49 per night
SUPERHOST
  1. Private room
  2. Chicago
p05- SELF CHECK IN Downtown Chicago 8 minutes away
$35 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$41 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
$50 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$111 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
$63 per night
SUPERHOST
  1. Entire residential home
  2. Chicago
Quiet & Cozy Garden Unit with Private Entrance
$60 per night
SUPERHOST
  1. Private room
  2. Chicago
Entire floor urban retreat private guest suite
$59 per night
  1. Private room
  2. Chicago
m6- Self Check in 8 min to downtown Chicago
$41 per night
PLUS
  1. Entire residential home
  2. Chicago
Feel at Home in Chicago, with Parking, Steps from Evanston
$107 per night
  1. Entire residential home
  2. Elmhurst
Elmhurst NEW - Super Clean Modern Farmhouse!
$300 per night
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Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
$103 per night
SUPERHOST
  1. Private room
  2. Chicago
Casa de Sueño/Private Bathroom/Near Train/Loyola🌙😴
$37 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$87 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
$175 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
$115 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Perfect 1BR in Lincoln Park - Steps to DePaul!
$220 per night
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$92 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
CASA NEWPORT
$152 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ukrainian Village Garden Retreat
$131 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
♥Modern & Chic 3BR | Fireplace+Netflix+Parking♥
$145 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy Private Coach House
$79 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Garden Luxury condo in historic greystone.
$199 per night
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Apartments with WiFi

SUPERHOST
  1. Private room
  2. Chicago
Stylish & Ample 1PBR STAYCATION SPACE For You
$24 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Wicker★Park Blue Line Subway@Division East★Village
$79 per night
  1. Entire rental unit
  2. Forest Park
Mid-Century Modern Charm. Close to Chicago.
$87 per night
PLUS
  1. Entire rental unit
  2. Chicago
Redesigned Lower Level Studio in Historic Building
$130 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming apartment in Old Town
$115 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
$41 per night
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat
$34 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy loft in Chicago's Uptown near CTA/Red Line
$110 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Tiny Studio Apartment 94 Walk Score
$65 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
The Buck Stop
$109 per night
  1. Entire rental unit
  2. Chicago
Calming Edgewater Glen Sanctuary
$100 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
$58 per night
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Nearby destinations

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