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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 ($187). Conversely, the most expensive month to stay in Chicago is June ($652).

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

The cheapest day to stay in Chicago is Sunday ($254). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,113.

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 $213 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 $230 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 22 January 2026
For those on a budget, these are the cheapest holiday rentals available in Chicago for the selected dates. If you have the flexibility, change the dates selected to compare prices.
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
$230
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
$299
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,443 hotels in Chicago and price data was last updated on 22 January 2026. The average price for a hotel in Chicago is $390/night.
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
$157
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
$67
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
$59
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
$154
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 22 January 2026.
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 22 January 2026.

  • How much does a holiday rental in Chicago cost?

    $390 per night is how much a holiday rental in Chicago costs, on average. $18 per night was the cheapest price recently found by our users, though anything for $269 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 October, and the cheapest time to book is October.

  • What is the best Chicago holiday rental?

    The best holiday rental in Chicago is Hotel 55 Chicago Downtown, according to our user data. 1,112 users from HotelsCombined gave the Hotel 55 Chicago Downtown a 8.3/10 rating.

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

    If you’re looking to stay close to Chicago O'Hare Intl Airport for your trip to Chicago, then consider booking a The Greenleaf House holiday rental. This holiday apartment is just 20.2 km away from the Chicago airport.

  • What’s the most popular holiday rental in Chicago near Art Institute of Chicago?

    Hotel 55 Chicago Downtown is the most popular Chicago holiday rental near Art Institute of Chicago (the city’s most popular landmark). It’s a 1.5 km trip from Hotel 55 Chicago Downtown to Art Institute of Chicago. While there may be other holiday rentals near Art Institute of Chicago, Hotel 55 Chicago Downtown received high marks (8.3/10) from 1,112 users.

  • Are there any Bed & Breakfast holiday rentals in Chicago?

    If you’re looking to book a Bed & Breakfast holiday rental in Chicago, then you have 22 to choose from. We recommend looking at The Villa Toscana as it’s currently the most popular Bed & Breakfast rental among our users.

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Find better results for your stay in Chicago

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