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.

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.
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.
Enjoy Chicago’s Nightlife from Studio Apartment
PLUS
Entire rental unit · 2 guests · 1 bed · 1 bath
Enjoy Chicago’s Nightlife from Studio ApartmentKeep updated on work demands at a vintage-style wooden desk in the working corner of this gorgeous studio apartment. The combination of metals, velvet and wood in the interior make this a beautiful apartment and a contemporary dream. Please note that this unit is located above a late night bar, which may add to the charm of it for some but may also pose to be a noise nuisance for light sleepers. We encourage you to read the reviews of past guests to make an informed decision.

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. Entire residential home
  2. Worth
The Comfy King Ranch /King Bed/Fast WiFi/Free Pkg
$208 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$41 per night
SUPERHOST
  1. Private room
  2. Chicago
Entire floor urban retreat private guest suite
$68 per night
  1. Private room
  2. Chicago
Charming Basement with Private Bath- Sleeps 2
$20 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$112 per night
PLUS
  1. Entire residential home
  2. Chicago
Feel at Home in Chicago, with Parking, Steps from Evanston
$110 per night
SUPERHOST
  1. Private room
  2. Willow Springs
Garden Level King and 2 Twin Beds. OUTDOOR HOT TUB
$59 per night
SUPERHOST
  1. Private room
  2. Chicago
At the crossroads of comfort and care
$52 per night
SUPERHOST
  1. Private room
  2. Chicago
Super Cozy Bed/Bath in Awesome Andersonville Home!
$65 per night
SUPERHOST
  1. Entire residential home
  2. Chicago
Quiet & Cozy Garden Unit with Private Entrance
$58 per night
SUPERHOST
  1. Private room
  2. Bensenville
Cozy Bedroom near O`Hare Airport
$45 per night
SUPERHOST
  1. Private room
  2. Chicago
m5- Self check in near downtown Chicago
$40 per night

Pet-friendly apartments

  1. Entire rental unit
  2. Chicago
A Stylish, Clean & Homie 1-Bedroom 1-Bath Apart
$119 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Garden Luxury condo in historic greystone.
$199 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
$116 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
$107 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$93 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming Lincoln Square Apartment Location
$74 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$108 per night
  1. Entire rental unit
  2. Chicago
Short distance to the O'Hare or Downtown Chicago.
$120 per night
  1. Entire rental unit
  2. Chicago
Lovely Studio in Great Location Chicago
$91 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
✱ Bold & Swanky 2BR | Gourmet Kitchen + Netflix ✱
$97 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Perfect 1BR in Lincoln Park - Steps to DePaul!
$220 per night
  1. Entire rental unit
  2. Chicago
Lincoln Park / Old Town, Roomy Nook
$128 per night

Apartments with WiFi

  1. Entire rental unit
  2. Chicago
A Stylish, Clean & Homie 1-Bedroom 1-Bath Apart
$119 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Garden Luxury condo in historic greystone.
$199 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
★Bright & Bold 1BR in Roscoe Village + Fireplace★
$116 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
$107 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
$93 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming Lincoln Square Apartment Location
$74 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
✨Spacious Centrally Located West Loop Loft✨
$108 per night
  1. Entire rental unit
  2. Chicago
Short distance to the O'Hare or Downtown Chicago.
$120 per night
  1. Entire rental unit
  2. Chicago
Lovely Studio in Great Location Chicago
$91 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
✱ Bold & Swanky 2BR | Gourmet Kitchen + Netflix ✱
$97 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Perfect 1BR in Lincoln Park - Steps to DePaul!
$220 per night
  1. Entire rental unit
  2. Chicago
Lincoln Park / Old Town, Roomy Nook
$128 per night