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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 February ($404). Conversely, the most expensive month to stay in Chicago is November ($3,896).

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

The cheapest day to stay in Chicago is Thursday ($598). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $1,465.

How far ahead should you book a vacation rental in Chicago?

Save money by booking a vacation rental at least 64 days before your trip to Chicago. The lowest price found when booking 64 days ahead was $299 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 4,275 hotels in Chicago and price data was last updated on 24 July 2025. The average price for a hotel in Chicago is $727/night.
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
$101
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
$82
Avg. per night
View Deal
Just Minutes from Downtown Chicago
Just Minutes from Downtown Chicago

Just Minutes from Downtown Chicago

Chicago, IL, United States
7.0 km from city centre
Air conditioning
$341
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
$387
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 24 July 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 24 July 2025.

  • How much does a holiday rental in Chicago cost?

    $728/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that November is the most expensive month to book, and August is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $11/night. In general, any Chicago rental for $493 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 Bed & Breakfast holiday rentals in Chicago?

    At the moment, there are 22 properties listed as a Bed & Breakfast holiday rental in Chicago. A popular Bed & Breakfast in Chicago amongst our users is The Villa Toscana.

Find better results for your stay in Chicago

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.