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Holiday hires 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 day to stay in a vacation rental in Chicago?

The cheapest day to stay in Chicago is Sunday ($341). On the other hand, travellers can expect to pay the most on Friday, when the average nightly price is $717.

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

Save money by booking a vacation rental at least 50 days before your trip to Chicago. The lowest price found when booking 50 days ahead was $230 per night.

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Cheapest holiday rentals in Chicago, Illinois

For those on a budget, these are the cheapest holiday rentals available in Chicago for the selected dates. If you have the flexibility, change the dates selected to compare prices.
The Greenleaf House
The Greenleaf House

The Greenleaf House

1320 West Greenleaf Avenue, Chicago, IL, United States
15.3 km from city centre
Free Wi-Fi
Air conditioning
$90
Avg. per night
View Deal
FOUND Hotels, Chicago, Series by Marriott
FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott

613 North Wells Street, Chicago, IL, United States
2.0 km from city centre
Free Wi-Fi
$225
Avg. per night
View Deal
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
$368
Avg. per night
View Deal

Other accommodation in Chicago

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
$75
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
$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
1.6 km from city centre
Pool
Free Wi-Fi
$303
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
$323
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
$827
Avg. per night
View Deal

Where to stay in Chicago

Scroll to and zoom in on the areas in Chicago you plan on visiting to find nearby properties. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chicago

  • How much does a holiday rental in Chicago cost?

    $329 per night is how much a holiday rental in Chicago costs, on average. $40 per night was the cheapest price recently found by our users, though anything for $264 per night or less is a good deal. Keep in mind that Chicago holiday rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is July.

  • What is the best Chicago holiday rental?

    The best holiday rental in Chicago is Hotel 55 Chicago Downtown, according to our user data. 1,125 users from HotelsCombined gave the Hotel 55 Chicago Downtown a 8.3/10 rating.

  • 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 Art Institute of Chicago?

    Hotel 55 Chicago Downtown is the most popular Chicago holiday rental near Art Institute of Chicago (the city’s most popular landmark). It’s a 1.5 km trip from Hotel 55 Chicago Downtown to Art Institute of Chicago. While there may be other holiday rentals near Art Institute of Chicago, Hotel 55 Chicago Downtown received high marks (8.3/10) from 1,125 users.

  • Are there any Motel holiday rentals in Chicago?

    If you’re looking to book a Motel holiday rental in Chicago, then you have 9 to choose from. We recommend looking at Ohio House Motel as it’s currently the most popular Motel rental among our users.

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