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Vacation rentals in Chicago

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Chicago, United States
2 May — 3 May2
...and more

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Travel insights for vacation rentals in Chicago

Use these up-to-date, data-driven insights about booking a vacation rental in Chicago including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is February (C$ 284). Conversely, the most expensive month to stay in Chicago is September (C$ 1,210).

What is the cheapest day to stay in a vacation rental in Chicago?

The cheapest day to stay in Chicago is Thursday (C$ 334). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 589.

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 C$ 208 per night.
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Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 3,549 hotels in Chicago and price data was last updated on 25 April 2025. The average price for a hotel in Chicago is C$ 484/night.
Show all 3,549 stays
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
C$ 73
Avg. per night
View Deal
Hamtramck Hostel
Hamtramck Hostel

Hamtramck Hostel

2699 Holmes Street, Detroit, MI, United States
7.0 km from city centre
Free Wi-Fi
Parking
Air Conditioning
C$ 143
Avg. per night
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Chicago Getaway Hostel
Chicago Getaway Hostel

Chicago Getaway Hostel

616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
C$ 72
Avg. per night
View Deal
Ohio House Motel
Ohio House Motel

Ohio House Motel

600 N La Salle Dr, Chicago, IL, United States
1.9 km from city centre
Free Wi-Fi
C$ 155
Avg. per night
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Home2 Suites by Hilton Chicago River North
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

110 West Huron Street, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
C$ 208
Avg. per night
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Hilton Chicago
Hilton Chicago

Hilton Chicago

720 South Michigan Avenue, Chicago, IL, United States
0.4 km from city centre
Pool
Free Wi-Fi
C$ 291
Avg. per night
View Deal

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 25 April 2025.
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 25 April 2025.

  • How much does a vacation rental in Chicago cost?

    Chicago vacation rentals are C$ 484/night on average. However, you may find that prices fluctuate depending on the time of year. For example, July is the most expensive month to book a vacation rental in Chicago, and May is often the cheapest month to book. Recently, our users found rentals for C$ 9/night - which is currently the cheapest price. Keep in mind that anything C$ 353/night or less is still considered a good deal.

  • What part of Chicago is best to stay in?

    Downtown is the best part of Chicago to stay in based on our user data. Out of all our users who looked at Chicago vacation rentals, 0% of them looked for stays in the Downtown neighbourhood in the last year. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown happens to be the most popular vacation rental in the Downtown neighbourhood of Chicago.

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