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 February ($154). Conversely, the most expensive month to stay in Chicago is November ($1,864).
What is the cheapest day to stay in a vacation rental in Chicago?
The cheapest day to stay in Chicago is Monday ($245). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $339.
How far ahead should you book a vacation rental in Chicago?
Save money by booking a vacation rental at least 55 days before your trip to Chicago. The lowest price found when booking 55 days ahead was $146 per night.
Other accommodations in Chicago
Find the perfect vacation rental for your stay in Chicago. There are 3,551 hotels in Chicago and price data was last updated on juillet 3, 2025. The average price for a hotel in Chicago is $441/night.
30 East Hubbard Street, Chicago, IL, United States
1.0 mi from city centre
Pool
Free Wi-Fi
$197
Avg. per night
4900 South Lake Shore Drive, Chicago, IL, United States
5.3 mi from city centre
Pool
Free Wi-Fi
Parking
Airport shuttle
$166
Avg. per night
225 North Wabash Avenue, Chicago, IL, United States
0.8 mi from city centre
Free Wi-Fi
$219
Avg. per night
310 South Halsted Street, Chicago, IL, United States
1.0 mi from city centre
Free Wi-Fi
Air Conditioning
$61
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
$48
Avg. per night