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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 January (S$ 135). Conversely, the most expensive month to stay in Chicago is September (S$ 482).

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

The cheapest day to stay in Chicago is Friday (S$ 318). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 609.

How far ahead should you book a vacation rental in Chicago?

Save money by booking a vacation rental at least 79 days before your trip to Chicago. The lowest price found when booking 79 days ahead was S$ 137 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$ 262 per night. There is currently one property in Chicago that can be booked for this price. Level Chicago - Old Town is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 28 October 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.
Level Chicago - Old Town
Level Chicago - Old Town

Level Chicago - Old Town

1140 North Wells Street, Chicago, IL, United States
3.1 km from city centre
Free Wi-Fi
S$ 262
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,630 hotels in Chicago and price data was last updated on 28 October 2025. The average price for a hotel in Chicago is S$ 311/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
S$ 166
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$ 229
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$ 200
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
S$ 76
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

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 28 October 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 28 October 2025.

  • How much does a holiday rental in Chicago cost?

    On average, it costs S$ 312 per night for a Chicago holiday rental, but S$ 225 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$ 20 per night. If you can, try to avoid booking your rental October (as this is the most expensive month). Booking October (the cheapest month) may end up saving you money.

  • What’s the closest holiday rental to Chicago O'Hare Intl Airport?

    If you’re looking to stay close to Chicago O'Hare Intl Airport for your trip to Chicago, then consider booking a The Greenleaf House holiday rental. This holiday apartment is just 20.2 km away from the Chicago airport.

  • What part of Chicago is best to stay in?

    The most popular neighbourhood for holiday rentals in Chicago is Downtown, with 25% 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.

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.