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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 November (S$ 176). Conversely, the most expensive month to stay in Chicago is June (S$ 535).

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

The cheapest day to stay in Chicago is Sunday (S$ 222). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is S$ 640.

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$ 183 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$ 198 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 27 January 2026
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$ 198
Avg. per night
View Deal
Just Minutes from Downtown Chicago
Just Minutes from Downtown Chicago

Just Minutes from Downtown Chicago

Chicago, IL, United States
7.2 km from city centre
Air conditioning
S$ 258
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,452 hotels in Chicago and price data was last updated on 27 January 2026. The average price for a hotel in Chicago is S$ 312/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$ 57
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$ 50
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$ 132
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 27 January 2026.
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 27 January 2026.

  • How much does a holiday rental in Chicago cost?

    On average, it costs S$ 312 per night for a Chicago holiday rental, but S$ 216 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$ 9 per night. If you can, try to avoid booking your rental December (as this is the most expensive month). Booking January (the cheapest month) may end up saving you money.

  • What is the best Chicago holiday rental?

    While there may be other great holiday rentals in Chicago to choose from, Hotel 55 Chicago Downtown is currently considered the best, based on 1,112 HotelsCombined reviews and an average rating of 8.3/10.

  • 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’s the most popular holiday rental in Chicago near Grant Park?

    The most popular holiday rental near Chicago’s Grant Park is Hotel 55 Chicago Downtown. Hotel 55 Chicago Downtown has a review score of 8.3/10 from 1,112 HotelsCombined users and it’s located just 2.0 km from Grant Park.

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