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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.

Mid-Century Modern Charm. Close to Chicago.
Entire rental unit · 4 guests · 3 beds · 1 bath

Mid-Century Modern Charm. Close to Chicago.Step back in time a bit with our charming 2nd floor walk-up in a quiet suburb. Newly remodeled but with a vintage, welcoming vibe. A short walk to the train or a 20-minute drive to downtown Chicago. We live downstairs and are happy to say hi, or happy to leave you in peace, whichever you prefer. Free Parking. Great wifi. 3-season back porch. Feel free to relax in our welcoming back yard. Record Player (Real Vinyl!)

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.

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.

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
R527 ZAR per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
R609 ZAR per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu
R748 ZAR per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
R1,600 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
At the crossroads of comfort and care
R731 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
R934 ZAR per night
SUPERHOST
  1. Entire residential home
  2. Chicago
Quiet & Cozy Garden Unit with Private Entrance
R883 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Entire floor urban retreat private guest suite
R883 ZAR per night
  1. Entire residential home
  2. Evanston
Stunning, Sunny Flat with Beautiful Backyard
R1,932 ZAR per night
  1. Private room
  2. Chicago
m6- Self Check in 8 min to downtown Chicago
R598 ZAR per night
PLUS
  1. Entire residential home
  2. Chicago
Feel at Home in Chicago, with Parking, Steps from Evanston
R1,979 ZAR per night
  1. Entire residential home
  2. Elmhurst
Elmhurst NEW - Super Clean Modern Farmhouse!
R3,768 ZAR per night

Pet-friendly apartments

SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
R1,562 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Casa de Sueño/Private Bathroom/Near Train/Loyola🌙😴
R681 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
R1,279 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
R2,582 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
R1,694 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
R1,349 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
CASA NEWPORT
R2,238 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ukrainian Village Garden Retreat
R2,082 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
♥Modern & Chic 3BR | Fireplace+Netflix+Parking♥
R2,149 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy Private Coach House
R1,212 ZAR per night
  1. Entire rental unit
  2. Chicago
Angie’s Nest
R1,897 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Garden Luxury condo in historic greystone.
R2,936 ZAR per night

Apartments with WiFi

PLUS
  1. Entire rental unit
  2. Chicago
Garden Retreat in a Tranquil Location in West Lakeview
R1,734 ZAR per night
  1. Entire rental unit
  2. Chicago
1 Bedroom Apartment by McCormick Place & Chinatown
R889 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Wicker★Park Blue Line Subway@Division East★Village
R1,154 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Logan Square/Avondale Chic Retreat W/Peloton Bike
R1,412 ZAR per night
PLUS
  1. Entire rental unit
  2. Chicago
Redesigned Lower Level Studio in Historic Building
R1,918 ZAR per night
PLUS
  1. Entire rental unit
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
R1,454 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
R710 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming apartment in Old Town
R1,696 ZAR per night
  1. Private room
  2. Chicago
Cozy guest room in sunny, expansive garden flat
R438 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Beautiful and spacious West Loop apartment.
R3,125 ZAR per night
  1. Entire rental unit
  2. Chicago
Calming Edgewater Glen Sanctuary
R1,507 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
CLEAN Cozy Vintage Chicago Apartment near Downtown
R1,245 ZAR per night

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