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Holiday rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use these up-to-date, data-driven insights about booking a holiday 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 April (€110). Conversely, the most expensive month to stay in Chicago is September (€504).

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

The cheapest day to stay in Chicago is Wednesday (€158). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is €247.

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 €135 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,460 hotels in Chicago and price data was last updated on 13 May 2025. The average price for a hotel in Chicago is €277/night.
Show all 3,460 stays
Courtyard by Marriott Chicago Downtown/River North
Courtyard by Marriott Chicago Downtown/River North

Courtyard by Marriott Chicago Downtown/River North

30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
€173
Avg. per night
View Deal
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
€149
Avg. per night
View Deal
Chicago Lake Shore Hotel
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 South Lake Shore Drive, Chicago, IL, United States
8.5 km from city centre
Pool
Free Wi-Fi
Parking
Airport shuttle
€149
Avg. per night
View Deal
Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air conditioning
€48
Avg. per night
View Deal
Wrigley Hostel
Wrigley Hostel

Wrigley Hostel

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
€42
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 13 May 2025.
Use the map to find holiday rentals in Chicago that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

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 13 May 2025.

  • How much does a holiday rental in Chicago cost?

    The average cost for a holiday rental in Chicago is €277/night. A good holiday rental deal in Chicago would be for €197/night or less. The cheapest rental deal found recently by our users was €22/night. If you’re flexible with your travel dates, then try to avoid booking September, the most expensive month of the year. Booking July is the cheapest month to book a holiday rental in Chicago.

  • What part of Chicago is best to stay in?

    The best neighbourhood to stay in Chicago is Downtown, according to our user data. 5% of our users who looked for holiday rentals in Chicago searched for properties in the Downtown area. If you’re also interested in booking a holiday rental in Downtown, consider the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown - the neighbourhood’s most popular rental property.

  • Are there any Motel holiday rentals in Chicago?

    There are 34 holiday rentals in Chicago that fall under the Motel category, the most popular is Motel 6 Elk Grove Village - O'Hare.

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