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Holiday rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Chicago.

What is the cheapest month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is January (£53). Conversely, the most expensive month to stay in Chicago is March (£273).

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

The cheapest day to stay in Chicago is Thursday (£108). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is £196.

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 £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 £51 per night. There is currently one property in Chicago that can be booked for this price. Econo Lodge is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 19 August 2025
These Chicago properties charge the lowest price per night of those we've come across. Prices will typically fluctuate depending on the dates selected, star rating of holiday rental, and holiday rental location.
Econo Lodge
Econo Lodge

Econo Lodge

Shorewood, IL, United States
0.9 mi from city centre
Air conditioning
£51
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 4,313 hotels in Chicago and price data was last updated on 19 August 2025. The average price for a hotel in Chicago is £171/night.
Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
1.0 mi from city centre
Free Wi-Fi
Air conditioning
£43
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
£35
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
1.0 mi from city centre
Pool
Free Wi-Fi
£161
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
0.8 mi from city centre
Free Wi-Fi
£143
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 19 August 2025.
Scroll to and zoom in on the areas in Chicago you plan on visiting to find nearby properties. 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 19 August 2025.

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £172/night on average. However, you may find that prices fluctuate depending on the time of year. For example, August is the most expensive month to book a holiday rental in Chicago, and May is often the cheapest month to book. Recently, our users found rentals for £12/night - which is currently the cheapest price. Keep in mind that anything £114/night or less is still considered a good deal.

  • What part of Chicago is best to stay in?

    Consider staying in Downtown when looking for Chicago holiday rentals. Downtown is the most popular neighbourhood in the city according to our users. In fact, out of all users who looked for holiday rentals in Chicago in the past year, 1% of them searched for rentals in Downtown. If it’s available, we recommend staying at the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown, a HotelsCombined favourite when it comes to holiday rentals in Chicago’s Downtown neighbourhood.

  • Are there any Aparthotel holiday rentals in Chicago?

    If you’re looking to book a Aparthotel holiday rental in Chicago, then you have 50 to choose from. We recommend looking at Sentral Michigan Avenue as it’s currently the most popular Aparthotel rental among our users.

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 £37 and Hotels Under £74. Discover hotel discounts now and make your hotel reservation today.