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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 Thursday (£144). On the other hand, travellers can expect to pay the most on Wednesday, when the average nightly price is £267.

How early should you book a vacation rental in Chicago?

Book at least 50 days before your stay begins to get the best price for your Chicago vacation rental.

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Cheapest holiday rentals in Chicago, Illinois

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.
The Greenleaf House
The Greenleaf House

The Greenleaf House

1320 West Greenleaf Avenue, Chicago, IL, United States
9.5 mi from city centre
Free Wi-Fi
Air conditioning
£50
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
1.2 mi from city centre
Free Wi-Fi
£135
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
1.9 mi from city centre
Free Wi-Fi
£198
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
1.0 mi from city centre
Free Wi-Fi
Air conditioning
£50
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
£54
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
£187
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
£156
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
0.8 mi from city centre
Free Wi-Fi
£185
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 a property's name will unlock more information and allow you to book that particular holiday rental.

Facts about staying in Chicago

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £196/night on average. However, you may find that prices fluctuate depending on the time of year. For example, November is the most expensive month to book a holiday rental in Chicago, and August is often the cheapest month to book. Recently, our users found rentals for £12/night - which is currently the cheapest price. Keep in mind that anything £148/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 1,117 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 1,117 HotelsCombined travellers. North Pier Apartments is also conveniently located just 0.6 mi from this holiday rental.

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