Vacation Apartment Rentals in Chicago, IL

Compare 3,518 available, short term vacation home properties, starts from $27

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Vacation Apartment Rentals in Chicago, IL Area: Top Deals

Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
Forrestville Ave Apartment
4.4 (30 reviews)
Forrestville Ave Apartment
Apartment
$89 /night
View deal
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
4.9 (31 reviews)
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
Apartment · 8 Guests · 3 Bedrooms
$195 /night*
View deal
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
4.8 (10 reviews)
Private Apartment With A Private Entrance To Our Cozy Newly Renovated Apartment
Apartment · 4 Guests · 2 Bedrooms
$83 /night*
View deal
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
Downtown Chicago McCormick Place beautiful apartment - 203
4.7 (5 reviews)
Downtown Chicago McCormick Place beautiful apartment - 203
Apartment
$195 /night
View deal
Search all

Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Chicago, IL Area?
Vacation Apartment & House Rental Price Information in Chicago, IL
+
The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
+
17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
What Are The Must-Visit Places in Chicago, IL?
Top Things to do in Chicago, IL
+
Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL
+

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers