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Vacation rentals in Chicago

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Travel insights for vacation rentals in Chicago

Use these up-to-date, data-driven insights about booking a vacation 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 (C$ 266). Conversely, the most expensive month to stay in Chicago is March (C$ 957).

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

The cheapest day to stay in Chicago is Sunday (C$ 312). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 810.

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 C$ 250 per night.
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Cheapest vacation 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 C$ 97 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 25 August 2025
Currently, these are the lowest-priced vacation rentals in Chicago we've come across for the dates selected. Consider alternative dates if you're able to compare prices.
Econo Lodge
Econo Lodge

Econo Lodge

Shorewood, IL, United States
1.5 km from city centre
Air Conditioning
C$ 97
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 4,310 hotels in Chicago and price data was last updated on 25 August 2025. The average price for a hotel in Chicago is C$ 335/night.
Ohio House Motel
Ohio House Motel

Ohio House Motel

600 N La Salle Dr, Chicago, IL, United States
1.9 km from city centre
Free Wi-Fi
C$ 185
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
1.6 km from city centre
Pool
Free Wi-Fi
C$ 293
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
C$ 268
Avg. per night
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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
C$ 80
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
C$ 64
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 25 August 2025.
Scroll through the map to find vacation rentals close to the Chicago neighborhood(s) you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 25 August 2025.

  • How much does a vacation rental in Chicago cost?

    Chicago vacation rentals are C$ 336/night on average. However, you may find that prices fluctuate depending on the time of year. For example, August is the most expensive month to book a vacation rental in Chicago, and August is often the cheapest month to book. Recently, our users found rentals for C$ 42/night - which is currently the cheapest price. Keep in mind that anything C$ 228/night or less is still considered a good deal.

  • 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 vacation rentals, 0% 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 vacation rental in the Downtown neighbourhood of Chicago.

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.