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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 (€127). Conversely, the most expensive month to stay in Chicago is August (€342).

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

The cheapest day to stay in Chicago is Wednesday (€191). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is €324.

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 €134 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 €173 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
At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Chicago. Prices will typically fluctuate depending on the dates selected, star rating of holiday rental, and holiday rental location.
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
€173
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 €212/night.
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
€51
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
€43
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
€110
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
€134
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
€379
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.
Use the map to find holiday rentals in Chicago that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

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?

    The average cost for a holiday rental in Chicago is €212/night. A good holiday rental deal in Chicago would be for €153/night or less. The cheapest rental deal found recently by our users was €23/night. If you’re flexible with your travel dates, then try to avoid booking October, the most expensive month of the year. Booking October is the cheapest month to book a holiday rental in Chicago.

  • 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 part of Chicago is best to stay in?

    The best neighbourhood to stay in Chicago is Downtown, according to our user data. 3% of our users who looked for holiday rentals in Chicago searched for properties in the Downtown area. If you’re also interested in booking a holiday rental in Downtown, consider the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown - the neighbourhood’s most popular rental property.

  • Are there any Motel holiday rentals in Chicago?

    There are 34 holiday rentals in Chicago that fall under the Motel category, the most popular is Ohio House Motel.

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