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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 day to stay in a vacation rental in Chicago?

The cheapest day to stay in Chicago is Saturday ($441). On the other hand, travellers can expect to pay the most on Thursday, when the average nightly price is $852.

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 $282 per night.

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Cheapest holiday rentals in Chicago, Illinois

Currently, these are the lowest-priced holiday rentals in Chicago we've come across for the dates selected. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
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
$110
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
$272
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
$455
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
$372
Avg. per night
View Deal
Omni Chicago Hotel
Omni Chicago Hotel

Omni Chicago Hotel

676 North Michigan Avenue, Chicago, IL, United States
2.1 km from city centre
Free Wi-Fi
$472
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
$392
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
Air conditioning
$92
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
$117
Avg. per night
View Deal

Where to stay in Chicago

Utilise the map to find properties close to the Chicago area(s) or attractions you plan on visiting. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Chicago

  • How much does a holiday rental in Chicago cost?

    $430/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that September is the most expensive month to book, and July is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $49/night. In general, any Chicago rental for $350 or less is a good deal.

  • What is the best Chicago holiday rental?

    Hotel 55 Chicago Downtown is considered the best Chicago holiday rental based on HotelsCombined user data. Hotel 55 Chicago Downtown has an average rating of 8.3/10 and 1,123 reviews.

  • What’s the closest holiday rental to Chicago O'Hare Intl Airport?

    It’s only 20.2 km from Chicago O'Hare Intl Airport to The Greenleaf House (the nearest Chicago holiday rental to the airport).

  • What’s the most popular holiday rental in Chicago near Magnificent Mile?

    With a score of 8.3/10 from 1,123 reviews, Hotel 55 Chicago Downtown is the most popular holiday rental in Chicago that’s close to Magnificent Mile (just 0.2 km away).

  • Are there any Inn holiday rentals in Chicago?

    At the moment, there are 5 properties listed as a Inn holiday rental in Chicago. A popular Inn in Chicago amongst our users is Rodeway Inn Chicago North Shore - Lincolnwood.

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