Vacation rentals in Chicago
Search and compare Chicago, IL vacation rentals from hundreds of travel sites on HotelsCombined and save.
Chicago, United States
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Travel insights for vacation rentals in Chicago
Use our HotelsCombined data-powered tips to help you find your next vacation rental in Chicago.
What is the cheapest month to book a vacation rental in Chicago?
The cheapest month to book a vacation rental in Chicago is February ($154). Conversely, the most expensive month to stay in Chicago is September ($651).
What is the cheapest day to stay in a vacation rental in Chicago?
The cheapest day to stay in Chicago is Sunday ($155). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $392.
How far ahead should you book a vacation rental in Chicago?
Save money by booking a vacation rental at least 66 days before your trip to Chicago. The lowest price found when booking 66 days ahead was $150 per night.
Other accommodations in Chicago
Find the perfect vacation rental for your stay in Chicago. There are 3,452 hotels in Chicago and price data was last updated on marzo 26, 2025. The average price for a hotel in Chicago is $274/night.
Show all 3,452 stays
701 North Michigan Avenue, Chicago, IL, United States
1.3 mi from city centre
Free Wi-Fi
$112
Avg. per night
720 South Michigan Avenue, Chicago, IL, United States
0.3 mi from city centre
Pool
Free Wi-Fi
$197
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
1.5 mi from city centre
Pool
Free Wi-Fi
$444
Avg. per night
24 East Ida B. Wells Drive, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$64
Avg. per night
2699 Holmes Street, Detroit, MI, United States
4.3 mi from city centre
Free Wi-Fi
Parking
Air Conditioning
$99
Avg. per night
616 West Arlington Place, Chicago, IL, United States
3.6 mi from city centre
Free Wi-Fi
$55
Avg. per night