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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 February ($148). Conversely, the most expensive month to stay in Chicago is September ($1,138).

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

The cheapest day to stay in Chicago is Monday ($193). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $341.

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 $150 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,551 hotels in Chicago and price data was last updated on 30 April 2025. The average price for a hotel in Chicago is $350/night.
Show all 3,551 stays
Home2 Suites by Hilton Chicago River North
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

110 West Huron Street, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
$155
Avg. per night
View Deal
Omni Chicago Hotel
Omni Chicago Hotel

Omni Chicago Hotel

676 North Michigan Avenue, Chicago, IL, United States
2.1 km from city centre
Free Wi-Fi
$248
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
$214
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
$45
Avg. per night
View Deal
Hamtramck Hostel
Hamtramck Hostel

Hamtramck Hostel

2699 Holmes Street, Detroit, MI, United States
7.0 km from city centre
Free Wi-Fi
Parking
Air conditioning
$103
Avg. per night
View Deal
Chicago Getaway Hostel
Chicago Getaway Hostel

Chicago Getaway Hostel

616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
$52
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 30 April 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 30 April 2025.

  • How much does a holiday rental in Chicago cost?

    The average cost for a holiday rental in Chicago is $350/night. A good holiday rental deal in Chicago would be for $246/night or less. The cheapest rental deal found recently by our users was $7/night. If you’re flexible with your travel dates, then try to avoid booking September, the most expensive month of the year. Booking May is the cheapest month to book a holiday rental in Chicago.

  • What part of Chicago is best to stay in?

    Downtown is the best part of Chicago to stay in based on our user data. Out of all our users who looked at Chicago holiday rentals, 19% of them looked for stays in the Downtown neighbourhood in the last year. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown happens to be the most popular holiday rental in the Downtown neighbourhood of Chicago.

  • Are there any Motel holiday rentals in Chicago?

    Yes, there are 34 Motel holiday rentals in Chicago. According to our data, Motel 6 Elk Grove Village - O'Hare is currently the most popular Motel rental in the city.

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