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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 ($174). Conversely, the most expensive month to stay in Chicago is November ($1,177).

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

The cheapest day to stay in Chicago is Saturday ($274). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $502.

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 $181 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 $70 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 30 July 2025
At the moment, these vacation rentals offer the lowest nightly rate out of those we've come across in Chicago. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Econo Lodge
Econo Lodge

Econo Lodge

Shorewood, IL, United States
1.5 km from city centre
Air conditioning
$70
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 4,272 hotels in Chicago and price data was last updated on 30 July 2025. The average price for a hotel in Chicago is $345/night.
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
$234
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
$267
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
$250
Avg. per night
View Deal
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
$61
Avg. per night
View Deal
Wrigley Hostel
Wrigley Hostel

Wrigley Hostel

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
$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 July 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 July 2025.

  • How much does a holiday rental in Chicago cost?

    The average cost for a holiday rental in Chicago is $346/night. A good holiday rental deal in Chicago would be for $256/night or less. The cheapest rental deal found recently by our users was $16/night. If you’re flexible with your travel dates, then try to avoid booking November, 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, 16% 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.

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 hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly. Discover hotel discounts now and make your hotel reservation today.