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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 December (S$ 226). Conversely, the most expensive month to stay in Chicago is March (S$ 842).

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

The cheapest day to stay in Chicago is Sunday (S$ 379). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 705.

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 S$ 232 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 S$ 94 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 13 September 2025
Out of the vacation rentals in Chicago we've come across, these properties are priced the lowest. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Econo Lodge
Econo Lodge

Econo Lodge

Shorewood, IL, United States
1.4 km from city centre
Air conditioning
S$ 94
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 4,002 hotels in Chicago and price data was last updated on 13 September 2025. The average price for a hotel in Chicago is S$ 321/night.
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
S$ 98
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
S$ 77
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
S$ 251
Avg. per night
View Deal
Kimpton Gray Hotel
Kimpton Gray Hotel

Kimpton Gray Hotel

122 West Monroe Street, Chicago, IL, United States
0.7 km from city centre
S$ 300
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
S$ 267
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 13 September 2025.
Use the map to find vacation rentals in Chicago that are close to the points of interest you'll be frequenting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

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 13 September 2025.

  • How much does a holiday rental in Chicago cost?

    On average, it costs S$ 322 per night for a Chicago holiday rental, but S$ 208 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Chicago was for S$ 15 per night. If you can, try to avoid booking your rental August (as this is the most expensive month). Booking September (the cheapest month) may end up saving you money.

  • What part of Chicago is best to stay in?

    The most popular neighbourhood for holiday rentals in Chicago is Downtown, with 33% of our users searching for rentals in this area over the last 12 months. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown is a popular holiday rental in Downtown that might be available for your travel dates, though there are other great properties in the area as well.

  • Are there any Guest house holiday rentals in Chicago?

    There are 16 holiday rentals in Chicago that fall under the Guest house category, the most popular is Hollywood Rentals Llc.

Find better results for your stay in Chicago

Consider other places to stay in Chicago

Stay at one of these places that users have found on HotelsCombined.
Chicago Bed & Breakfasts
Chicago Inns
Chicago Motels
Chicago Resorts

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