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 February (€107). Conversely, the most expensive month to stay in Chicago is November (€1,032).

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

The cheapest day to stay in Chicago is Thursday (€159). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is €388.

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 €154 per night.

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 24 July 2025. The average price for a hotel in Chicago is €374/night.
30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
€199
Avg. per night
110 West Huron Street, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
€173
Avg. per night
225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
Free Wi-Fi
€209
Avg. per night
310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air conditioning
€52
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
€42
Avg. per night

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 24 July 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 24 July 2025.
  • How much does a holiday rental in Chicago cost?

    The average cost for a holiday rental in Chicago is €375/night. A good holiday rental deal in Chicago would be for €254/night or less. The cheapest rental deal found recently by our users was €6/night. If you’re flexible with your travel dates, then try to avoid booking November, the most expensive month of the year. Booking August is the cheapest month to book a holiday rental in Chicago.

  • What part of Chicago is best to stay in?

    The best neighbourhood to stay in Chicago is Downtown, according to our user data. 5% 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 Motel 6 Elk Grove Village - O'Hare.

Find better results for your stay in Chicago

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