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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 April (£78). Conversely, the most expensive month to stay in Chicago is September (£358).

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

The cheapest day to stay in Chicago is Wednesday (£112). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is £176.

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 £114 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,460 hotels in Chicago and price data was last updated on 13 May 2025. The average price for a hotel in Chicago is £233/night.
Show all 3,460 stays
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
£40
Avg. per night
View Deal
Wrigley Hostel
Wrigley Hostel

Wrigley Hostel

3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
£36
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
£146
Avg. per night
View Deal
Chicago Lake Shore Hotel
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 South Lake Shore Drive, Chicago, IL, United States
5.3 mi from city centre
Pool
Free Wi-Fi
Parking
Airport shuttle
£126
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
£175
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 13 May 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 13 May 2025.

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £234/night on average. However, you may find that prices fluctuate depending on the time of year. For example, September is the most expensive month to book a holiday rental in Chicago, and July is often the cheapest month to book. Recently, our users found rentals for £19/night - which is currently the cheapest price. Keep in mind that anything £166/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.

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