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 day to stay in a vacation rental in Chicago?
The cheapest day to stay in Chicago is Sunday (C$ 358). On the other hand, travellers can expect to pay the most on Thursday, when the average nightly price is C$ 486.
How far ahead should you book a vacation rental in Chicago?
Save money by booking a vacation rental at least 82 days before your trip to Chicago. The lowest price found when booking 82 days ahead was C$ 182 per night.
Cheapest vacation rentals in Chicago, Illinois
Discover affordable stays in Chicago that provide a quality experience without breaking the bank. Hotels in Chicago can be found for as low as C$ 80 per night. There is currently one property in Chicago that can be booked for this price. The Greenleaf House is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 9 October 2026
Currently, these are the lowest-priced vacation rentals in Chicago we've come across for the dates selected. Consider alternative dates if you're able to compare prices.
1320 West Greenleaf Avenue, Chicago, IL, United States
15.3 km from city centre
Free Wi-Fi
Air Conditioning
C$ 80
Avg. per night
Chicago, IL, United States
5.3 km from city centre
Air Conditioning
Airport shuttle
C$ 166
Avg. per night
613 North Wells Street, Chicago, IL, United States
2.0 km from city centre
Free Wi-Fi
C$ 179
Avg. per night
1140 North Wells Street, Chicago, IL, United States
3.1 km from city centre
Free Wi-Fi
C$ 364
Avg. per night
Other accommodations in Chicago
Find the perfect vacation rental for your stay in Chicago. There are 2,630 hotels in Chicago and price data was last updated on 9 October 2026. The average price for a hotel in Chicago is .
5990 North Ridge Avenue, Chicago, IL, United States
13.2 km from city centre
Free Wi-Fi
Parking
C$ 133
Avg. per night
30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
C$ 212
Avg. per night
225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
Free Wi-Fi
C$ 226
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
C$ 762
Avg. per night
310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air Conditioning
C$ 73
Avg. per night
24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
C$ 80
Avg. per night
Where to stay in Chicago
Explore different neighbourhoods and areas within Chicago to find the perfect location for your stay. Map data was last updated on 9 October 2026.
Scroll through the map to find vacation rentals close to the Chicago neighborhood(s) you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.
Facts about staying in Chicago
Find useful tips and insights about staying in Chicago to help you make the most of your experience. FAQs were last updated on 9 October 2026.
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