Vacation rentals in Chicago
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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 April ($141). Conversely, the most expensive month to stay in Chicago is September ($737).
What is the cheapest day to stay in a vacation rental in Chicago?
The cheapest day to stay in Chicago is Wednesday ($196). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $348.
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 3,460 hotels in Chicago and price data was last updated on mayo 12, 2025. The average price for a hotel in Chicago is $323/night.
Show all 3,460 stays
310 South Halsted Street, Chicago, IL, United States
1.0 mi from city centre
Free Wi-Fi
Air Conditioning
$53
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
$47
Avg. per night
30 East Hubbard Street, Chicago, IL, United States
1.0 mi from city centre
Pool
Free Wi-Fi
$193
Avg. per night