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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 ($256). Conversely, the most expensive month to stay in Chicago is August ($691).

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

The cheapest day to stay in Chicago is Wednesday ($385). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $654.

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

Save money by booking a vacation rental at least 79 days before your trip to Chicago. The lowest price found when booking 79 days ahead was $272 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 $352 per night. There is currently one property in Chicago that can be booked for this price. Level Chicago - Old Town is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 23 October 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.
Level Chicago - Old Town
Level Chicago - Old Town

Level Chicago - Old Town

1140 North Wells Street, Chicago, IL, United States
3.1 km from city centre
Free Wi-Fi
$352
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,628 hotels in Chicago and price data was last updated on 23 October 2025. The average price for a hotel in Chicago is $428/night.
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
$223
Avg. per night
View Deal
Kimpton Gray Hotel
Kimpton Gray Hotel

Kimpton Gray Hotel

122 West Monroe Street, Chicago, IL, United States
0.7 km from city centre
$316
Avg. per night
View Deal
L7 Chicago by LOTTE
L7 Chicago by LOTTE

L7 Chicago by LOTTE

225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
Free Wi-Fi
$275
Avg. per night
View Deal
Just Minutes from Downtown Chicago
Just Minutes from Downtown Chicago

Just Minutes from Downtown Chicago

Chicago, IL, United States
7.2 km from city centre
Air conditioning
$329
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
$106
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
$96
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 23 October 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 23 October 2025.

  • How much does a holiday rental in Chicago cost?

    $429/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that October 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 $47/night. In general, any Chicago rental for $308 or less is a good deal.

  • What’s the closest holiday rental to Chicago O'Hare Intl Airport?

    It’s only 20.2 km from Chicago O'Hare Intl Airport to The Greenleaf House (the nearest Chicago holiday rental to the airport).

  • What part of Chicago is best to stay in?

    Downtown is the most popular area of Chicago to stay in. In the past year, 20% 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 Aparthotel holiday rentals in Chicago?

    At the moment, there are 50 properties listed as a Aparthotel holiday rental in Chicago. A popular Aparthotel in Chicago amongst our users is Private Room in Stylish Humboldt Park Retreat.

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Find better results for your stay in Chicago

Consider other places to stay in Chicago

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Chicago Inns

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