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Vacation 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 November (₹ 1,075,527). Conversely, the most expensive month to stay in Chicago is March (₹ 3,781,874).

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

The cheapest day to stay in Chicago is Tuesday (₹ 1,649,238). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is ₹ 2,675,030.

How far ahead should you book a vacation rental in Chicago?

Save money by booking a vacation rental at least 55 days before your trip to Chicago. The lowest price found when booking 55 days ahead was ₹ 12,510 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,510 hotels in Chicago and price data was last updated on 15 June 2025. The average price for a hotel in Chicago is ₹ 25,425/night.
Show all 3,510 stays
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
₹ 4,567
Avg. per night
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Wrigley Hostel
Wrigley Hostel

Wrigley Hostel

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
₹ 4,021
Avg. per night
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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
₹ 16,525
Avg. per night
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Chicago Lake Shore Hotel
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 South Lake Shore Drive, Chicago, IL, United States
8.5 km from city centre
Pool
Free Wi-Fi
Parking
Airport shuttle
₹ 14,224
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 15 June 2025.
Navigate to the areas in Chicago you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation rental within the map by clicking on its name.

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 15 June 2025.

  • How much does a holiday rental in Chicago cost?

    A holiday rental in Chicago will cost ₹ 25,425 per night on average. However some users found rentals for as low as ₹ 1,338 per night. A good deal on a Chicago holiday rental would be anything for ₹ 18,252 per night or less. Keep in mind that booking July may be more expensive, whereas booking May is the cheapest month of the year to book.

  • What part of Chicago is best to stay in?

    Downtown is the best part of the city to stay in if you’re looking for a holiday rental in Chicago. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Chicago, 4% of HotelsCombined users searched for rentals in Downtown in the past 12 months, making it a popular choice.

  • Are there any Motel holiday rentals in Chicago?

    34 Motel holiday rentals are available in Chicago. Based on our user data, the most popular is Ohio House Motel - so we recommend seeing if this property is available for your travel dates before looking at other Motel options in Chicago.

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