Skip to content

Vacation rentals in Downtown Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Downtown Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guesthouse · 3 guests · 1 bed · 1 bath
Private Studio in Bridgeport, ChicagoA bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
Restoring Chicago speakeasy of the 1920s room 3A
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
Restoring Chicago speakeasy of the 1920s room 3AIf you are having trouble booking a night call me. Michael: 3124515213 My son Todd and I are currently restoring a gem from Chicago's history. we have made great progress in the last year and now our down to simple painting touch-ups Come be part of it. M&T
Polk Street Coach House Apartment, Little Italy/Medical Dist
PLUS
Entire guesthouse · 6 guests · 2 beds · 1 bath
Polk Street Coach House Apartment, Little Italy/Medical DistCook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Downtown Chicago

SUPERHOST
  1. Private room
  2. Chicago
SHARED Artist Loft . Very Unique
$96 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
$88 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Urban Comfort in the Heart of Chicago
$78 per night
SUPERHOST
  1. Private room
  2. Chicago
🌟 Cozy Bedroom by Downtown & Train; Rooftop Deck!🌟
$41 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
Lincoln Park North Pond 2 Bedroom Pied-à-Terre
$110 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cabin #301 at 747 Lofts
$72 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Grand Avenue APT 2/West Loop & newly renovated!
$146 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Beautiful and spacious West Loop apartment.
$170 per night
  1. Entire rental unit
  2. Chicago
Spacious Studio - Everything & More in Gold Coast!
$90 per night
SUPERHOST
  1. Entire residential home
  2. Chicago
LUXURIOUS LINCOLN PARK Home w/ Rooftop (+parking)
$104 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great Location Studio III
$57 per night
  1. Entire rental unit
  2. Chicago
The Executive's Escape (2BR)
$225 per night