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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.

Spacious, light-drenched studio-private entrance!
SUPERHOST
Entire apartment · 2 guests · 1 bed · 1.5 baths

Spacious, light-drenched studio-private entrance!Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

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. Willow Springs
Catmandu
R695 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Luxury in Logan Square - The Pasadena Room
R1,368 ZAR per night
  1. Entire house
  2. Blue Island
Blue Island Living
R1,778 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Huge Victorian near Loyola, Lake #2
R953 ZAR per night
  1. Private room
  2. Chicago
R7 Suite with Private full Bathroom in Bridgeport
R673 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Room for solo traveler near midway airport suite B
R343 ZAR per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
R590 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Downtown Chicago only 8 minutes away New Queen Bed
R570 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Beautiful bedroom with private bath
R979 ZAR per night
  1. Entire house
  2. Berwyn
PrivateTudor in-law suite
R1,312 ZAR per night
  1. Private room
  2. Alsip
Safe clean charming close transportation Viva!
R701 ZAR per night
SUPERHOST
  1. Private room
  2. Oak Park
warm comfortable home with lots to offer
R416 ZAR per night

Pet-friendly apartments

SUPERHOST
  1. Entire apartment
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
R1,348 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
1 bedroom Wrigleyville
R1,829 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
R1,160 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Unwind in a Charming Apartment with Skylights
R1,784 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
R1,243 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
❤️ Cozy and Comfy 1BR Condo in Logan Square!
R1,916 ZAR per night
  1. Entire apartment
  2. Chicago
COOL PLACE - 10 MIN WALK FROM WRIGLEY FIELD
R1,283 ZAR per night
  1. Entire apartment
  2. Chicago
Spacious & bright 2BR Boho-Chic vibe w parking
R1,413 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Modern, warm and welcoming apartment in A'Ville
R2,418 ZAR per night
  1. Entire apartment
  2. Chicago
Garden apartment in cute Avondale Area
R1,662 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Strictly Commercial Storefront: Humboldt, Bucktown
R1,585 ZAR per night
  1. Entire apartment
  2. Chicago
Safe/ EZ Traveling Apt. 2BED/1BATH
R1,085 ZAR per night

Apartments with WiFi

PLUS
  1. Entire apartment
  2. Chicago
Stunning Retro Apartment in Andersonville
R1,253 ZAR per night
SUPERHOST
  1. Private room
  2. Chicago
Cozy guest room 1 block from U of C
R553 ZAR per night
PLUS
  1. Entire apartment
  2. Chicago
Cozy and Stylish Studio with Free Parking in Irving Park
R1,362 ZAR per night
  1. Entire apartment
  2. Chicago
2-bed/1 bath urban garden retreat
R1,376 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Chicago Sanctuary: Perfect 1BD in West Town!
R732 ZAR per night
PLUS
  1. Entire apartment
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
R1,263 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Entire apartment 1br close to Downtown Chicago.
R829 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Basement Studio w/Free St. Parking, Humboldt Park
R799 ZAR per night
  1. Private room
  2. Chicago
Private rm: Home away from home.
R594 ZAR per night
  1. Entire apartment
  2. Chicago
Cozy Garden Studio in Woodlawn Neighborhood
R760 ZAR per night
  1. Entire apartment
  2. Chicago
Calming Edgewater Glen Sanctuary
R1,153 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Chicago
Wrigley Field 2nd floor Gem!
R1,368 ZAR per night

Nearby destinations