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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 January ($314). Conversely, the most expensive month to stay in Chicago is March ($1,473).

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

The cheapest day to stay in Chicago is Wednesday ($673). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $1,023.

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 $307 per night.
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Cheapest holiday 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 $120 per night. There is currently one property in Chicago that can be booked for this price. Econo Lodge is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 8 September 2025
Currently, these are the lowest-priced holiday rentals in Chicago we've come across for the dates selected. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Econo Lodge
Econo Lodge

Econo Lodge

Shorewood, IL, United States
1.4 km from city centre
Air conditioning
$120
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 4,109 hotels in Chicago and price data was last updated on 8 September 2025. The average price for a hotel in Chicago is $412/night.
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
$319
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
$98
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
$74
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
$307
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 8 September 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 8 September 2025.

  • How much does a holiday rental in Chicago cost?

    $412/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 October is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $42/night. In general, any Chicago rental for $281 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, 13% 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.

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.