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Holiday rentals in Chicago

Search and compare Chicago, IL holiday rentals from hundreds of travel sites on HotelsCombined and save.

Chicago, United States
30 Apr — 1 May2
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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 ($411). Conversely, the most expensive month to stay in Chicago is September ($1,753).

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

The cheapest day to stay in Chicago is Thursday ($484). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $853.

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 $250 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,556 hotels in Chicago and price data was last updated on 23 April 2025. The average price for a hotel in Chicago is $582/night.
Show all 3,556 stays
Warwick Allerton Chicago
Warwick Allerton Chicago

Warwick Allerton Chicago

701 North Michigan Avenue, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
$182
Avg. per night
View Deal
Ambassador Chicago
Ambassador Chicago

Ambassador Chicago

1301 North State Parkway, Chicago, IL, United States
3.4 km from city centre
Free Wi-Fi
$110
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
2.3 km from city centre
Pool
Free Wi-Fi
$807
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
$324
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
$88
Avg. per night
View Deal
Hamtramck Hostel
Hamtramck Hostel

Hamtramck Hostel

2699 Holmes Street, Detroit, MI, United States
7.0 km from city centre
Free Wi-Fi
Parking
Air conditioning
$172
Avg. per night
View Deal
Chicago Getaway Hostel
Chicago Getaway Hostel

Chicago Getaway Hostel

616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
$89
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 April 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 April 2025.

  • How much does a holiday rental in Chicago cost?

    $583/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that July is the most expensive month to book, and May 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 $425 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, 27% 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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