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Holiday hires in Chicago

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

Chicago, United States
1 May — 2 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 ($363). Conversely, the most expensive month to stay in Chicago is September ($1,545).

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

The cheapest day to stay in Chicago is Thursday ($426). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $751.

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 $235 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,549 hotels in Chicago and price data was last updated on 24 April 2025. The average price for a hotel in Chicago is $547/night.
Show all 3,549 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
$170
Avg. per night
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Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District

22 W. Monroe, Chicago, IL, United States
0.6 km from city centre
$272
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
$758
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
$83
Avg. per night
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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
$161
Avg. per night
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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
$68
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 April 2025.
Scroll to and zoom in on the areas in Chicago you plan on visiting to find nearby properties. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

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 April 2025.

  • How much does a holiday rental in Chicago cost?

    $547 per night is how much a holiday rental in Chicago costs, on average. $11 per night was the cheapest price recently found by our users, though anything for $399 per night or less is a good deal. Keep in mind that Chicago holiday rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is May.

  • What part of Chicago is best to stay in?

    Downtown is the best part of the city to stay in if you’re looking for a holiday rental in Chicago. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Chicago, 5% of HotelsCombined users searched for rentals in Downtown in the past 12 months, making it a popular choice.

  • Are there any Motel holiday rentals in Chicago?

    If you’re looking to book a Motel holiday rental in Chicago, then you have 34 to choose from. We recommend looking at Motel 6 Elk Grove Village - O'Hare as it’s currently the most popular Motel rental among our users.

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