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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 Wednesday (€212). On the other hand, travellers can expect to pay the most on Tuesday, when the average nightly price is €317.

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 €156 per night.

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Cheapest holiday rentals in Chicago, Illinois

At the moment, these holiday rentals offer the lowest nightly rate out of those we've come across in Chicago. 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
15.3 km from city centre
Free Wi-Fi
Air conditioning
€47
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
€101
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
€106
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
€199
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
Spa
€49
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
€50
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
€125
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
€197
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
€141
Avg. per night
View deal

Where to stay in Chicago

Use the map to find holiday rentals in Chicago that are close to the points of interest you'll be frequenting. 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?

    The average cost for a holiday rental in Chicago is €290/night. A good holiday rental deal in Chicago would be for €242/night or less. The cheapest rental deal found recently by our users was €27/night. If you’re flexible with your travel dates, then try to avoid booking December, the most expensive month of the year. Booking September is the cheapest month to book a holiday rental in Chicago.

  • 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 1,117 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 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 Magnificent Mile?

    If you’re looking for a holiday rental close to Magnificent Mile while in Chicago, then the most popular is The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel with a 8.3/10 review score from 1,117 users. The distance from Magnificent Mile to The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel is 0.2 km.

  • Are there any Inn holiday rentals in Chicago?

    There are 5 holiday rentals in Chicago that fall under the Inn category, the most popular is Rodeway Inn Chicago North Shore - Lincolnwood.

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