Insights
Where to stay

Vacation rentals in Chicago

Search and compare Chicago, IL holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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 April (S$ 233). Conversely, the most expensive month to stay in Chicago is September (S$ 1,062).

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

The cheapest day to stay in Chicago is Wednesday (S$ 334). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 521.

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 S$ 196 per night.
Find deals

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,460 hotels in Chicago and price data was last updated on 13 May 2025. The average price for a hotel in Chicago is S$ 402/night.
Show all 3,460 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
S$ 69
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
S$ 61
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
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
S$ 216
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$ 302
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 May 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 May 2025.

  • How much does a holiday rental in Chicago cost?

    On average, it costs S$ 403 per night for a Chicago holiday rental, but S$ 286 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$ 32 per night. If you can, try to avoid booking your rental September (as this is the most expensive month). Booking July (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 50% 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 Motel holiday rentals in Chicago?

    There are 34 holiday rentals in Chicago that fall under the Motel category, the most popular is Motel 6 Bridgeview.

Find better results for your stay in Chicago