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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 (£148). On the other hand, travellers can expect to pay the most on Tuesday, when the average nightly price is £299.

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

Save money by booking a vacation rental at least 87 days before your trip to Chicago. The lowest price found when booking 87 days ahead was £89 per night.

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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
£42
Avg. per night
View deal
Mccormick Place Guest House
Mccormick Place Guest House

Mccormick Place Guest House

Chicago, IL, United States
3.3 mi from city centre
Air conditioning
Airport shuttle
£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
1.2 mi from city centre
Free Wi-Fi
£98
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
£199
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
1.0 mi from city centre
Pool
Free Wi-Fi
£116
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
£114
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
£125
Avg. per night
View deal
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
£37
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 £197/night on average. However, you may find that prices fluctuate depending on the time of year. For example, September is the most expensive month to book a holiday rental in Chicago, and October 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 £147/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, The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel is currently considered the best, based on 1,122 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, The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel happens to be the most popular among our users. The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel has a current rating of 8.3 from 1,122 HotelsCombined travellers. North Pier Apartments is also conveniently located just 0.6 mi from this holiday rental.

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