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Holiday hires 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 ($339). Conversely, the most expensive month to stay in Chicago is November ($3,262).

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

The cheapest day to stay in Chicago is Thursday ($501). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $1,227.

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 $274 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 25 July 2025. The average price for a hotel in Chicago is $665/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
$354
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
$372
Avg. per night
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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
$817
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 25 July 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 25 July 2025.

  • How much does a holiday rental in Chicago cost?

    $666 per night is how much a holiday rental in Chicago costs, on average. $10 per night was the cheapest price recently found by our users, though anything for $451 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 November, and the cheapest time to book is August.

  • 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.

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 the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $151. Discover hotel discounts now and make your hotel reservation today.