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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 November ($401). Conversely, the most expensive month to stay in Chicago is September ($1,669).

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

The cheapest day to stay in Chicago is Monday ($494). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $964.

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 $243 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,512 hotels in Chicago and price data was last updated on 9 junio 2025. The average price for a hotel in Chicago is $542/night.
Show all 3,512 stays
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
$89
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
$78
Avg. per night
View Deal
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
$320
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
$276
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 9 junio 2025.
Utilise the map to find properties close to the Chicago area(s) or attractions you plan on visiting. Users can click on a holiday 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 junio 2025.

  • How much does a holiday rental in Chicago cost?

    $543/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that August is the most expensive month to book, and January is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $33/night. In general, any Chicago rental for $372 or less is a good deal.

  • What part of Chicago is best to stay in?

    Downtown is the most popular area of Chicago to stay in. In the past year, 25% of HotelsCombined users looking for Chicago holiday rentals searched within Downtown. Based on user data, the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown is one of the most popular holiday rentals in Downtown.

  • Are there any Motel holiday rentals in Chicago?

    At the moment, there are 34 properties listed as a Motel holiday rental in Chicago. A popular Motel in Chicago amongst our users is Motel 6-Schiller Park, Il - Chicago O'hare.

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