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Holiday rentals in Chicago

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

Chicago, United States
1 May — 2 May2
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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 February (£83). Conversely, the most expensive month to stay in Chicago is September (£356).

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

The cheapest day to stay in Chicago is Thursday (£98). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is £173.

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 £113 per night.
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Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,549 hotels in Chicago and price data was last updated on 24 April 2025. The average price for a hotel in Chicago is £262/night.
Show all 3,549 stays
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
£40
Avg. per night
View Deal
Hamtramck Hostel
Hamtramck Hostel

Hamtramck Hostel

2699 Holmes Street, Detroit, MI, United States
4.3 mi from city centre
Free Wi-Fi
Parking
Air conditioning
£77
Avg. per night
View Deal
Chicago Getaway Hostel
Chicago Getaway Hostel

Chicago Getaway Hostel

616 West Arlington Place, Chicago, IL, United States
3.6 mi from city centre
Free Wi-Fi
£39
Avg. per night
View Deal
Warwick Allerton Chicago
Warwick Allerton Chicago

Warwick Allerton Chicago

701 North Michigan Avenue, Chicago, IL, United States
1.3 mi from city centre
Free Wi-Fi
£82
Avg. per night
View Deal
Ambassador Chicago
Ambassador Chicago

Ambassador Chicago

1301 North State Parkway, Chicago, IL, United States
2.1 mi from city centre
Free Wi-Fi
£49
Avg. per night
View Deal
Hampton Inn Chicago McCormick Place
Hampton Inn Chicago McCormick Place

Hampton Inn Chicago McCormick Place

123 East Cermak, Suite 100, Chicago, IL, United States
1.6 mi from city centre
Pool
Free Wi-Fi
£119
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 24 April 2025.
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 24 April 2025.

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £263/night on average. However, you may find that prices fluctuate depending on the time of year. For example, July is the most expensive month to book a holiday rental in Chicago, and May is often the cheapest month to book. Recently, our users found rentals for £5/night - which is currently the cheapest price. Keep in mind that anything £191/night or less is still considered a good deal.

  • What part of Chicago is best to stay in?

    Consider staying in Downtown when looking for Chicago holiday rentals. Downtown is the most popular neighbourhood in the city according to our users. In fact, out of all users who looked for holiday rentals in Chicago in the past year, 1% of them searched for rentals in Downtown. If it’s available, we recommend staying at the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown, a HotelsCombined favourite when it comes to holiday rentals in Chicago’s Downtown neighbourhood.

  • Are there any Motel holiday rentals in Chicago?

    If you’re looking to book a Motel holiday rental in Chicago, then you have 34 to choose from. We recommend looking at Travelodge by Wyndham Chicago - South Holland as it’s currently the most popular Motel rental among our users.

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