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Holiday rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Chicago.

What is the cheapest month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is November (£97). Conversely, the most expensive month to stay in Chicago is October (£305).

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

The cheapest day to stay in Chicago is Sunday (£142). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is £348.

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 £62 per night.

Find deals

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 £141 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 2 April 2026
These Chicago properties charge the lowest price per night of those we've come across. Prices will typically fluctuate depending on the dates selected, star rating of holiday rental, and holiday rental location.
Level Chicago - Old Town
Level Chicago - Old Town

Level Chicago - Old Town

1140 North Wells Street, Chicago, IL, United States
1.9 mi from city centre
Free Wi-Fi
£141
Avg. per night
View Deal
The Greenleaf House
The Greenleaf House

The Greenleaf House

Chicago, IL, United States
9.5 mi from city centre
Air conditioning
Free Wi-Fi
£425
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,629 hotels in Chicago and price data was last updated on 2 April 2026. The average price for a hotel in Chicago is £171/night.
Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
1.0 mi from city centre
Free Wi-Fi
Air conditioning
£113
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£72
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
£96
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
1.0 mi from city centre
Pool
Free Wi-Fi
£126
Avg. per night
View Deal
Home2 Suites by Hilton Chicago River North
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

110 West Huron Street, Chicago, IL, United States
1.3 mi from city centre
Free Wi-Fi
£100
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 2 April 2026.
Scroll to and zoom in on the areas in Chicago you plan on visiting to find nearby properties. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

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 2 April 2026.

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £172/night on average. However, you may find that prices fluctuate depending on the time of year. For example, May is the most expensive month to book a holiday rental in Chicago, and March is often the cheapest month to book. Recently, our users found rentals for £19/night - which is currently the cheapest price. Keep in mind that anything £126/night or less is still considered a good deal.

  • 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 1,126 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 for Chicago holiday rentals that are close to Chicago O'Hare Intl Airport, then the nearest one is The Greenleaf House which is 12.5 mi away.

  • What’s the most popular holiday rental in Chicago near North Pier Apartments?

    While there may be several Chicago holiday rentals near North Pier Apartments, Hotel 55 Chicago Downtown happens to be the most popular among our users. Hotel 55 Chicago Downtown has a current rating of 8.3 from 1,126 HotelsCombined travellers. North Pier Apartments is also conveniently located just 0.6 mi from this holiday rental.

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