Best & Cheap Resorts in Chicago, IL

Compare 3,518 available, short term vacation home properties, starts from $37/night

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

Best & Cheap Resorts in Chicago, IL: Top Deals

The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
The Hotel at Midtown
4.5 (206 reviews)
The Hotel at Midtown
Resort
$271.15 /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 Rated Places to Visit 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