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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 Monday ($344). On the other hand, travellers can expect to pay the most on Saturday, when the average nightly price is $495.

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 $251 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
$79
Avg. per night
View deal
Mccormick Place Guest House
Mccormick Place Guest House

Mccormick Place Guest House

Chicago, IL, United States
5.3 km from city centre
Air conditioning
Airport shuttle
$162
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
$171
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
$331
Avg. per night
View deal

Other accommodation in Chicago

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
$203
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
$223
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
$750
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
Spa
$78
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
$94
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?

    $387 per night is how much a holiday rental in Chicago costs, on average. $43 per night was the cheapest price recently found by our users, though anything for $311 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 December, and the cheapest time to book is September.

  • What is the best Chicago holiday rental?

    The best holiday rental in Chicago is The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel, according to our user data. 1,117 users from HotelsCombined gave the The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel 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?

    The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel 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 The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel to Art Institute of Chicago. While there may be other holiday rentals near Art Institute of Chicago, The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel received high marks (8.3/10) from 1,117 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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Consider other places to stay in Chicago

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