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Vacation rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use these up-to-date, data-driven insights about booking a holiday rental in Chicago including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is February ($135). Conversely, the most expensive month to stay in Chicago is June ($831).

What is the cheapest day to stay in a vacation rental in Chicago?

The cheapest day to stay in Chicago is Wednesday ($203). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $424.

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

Save money by booking a vacation rental at least 68 days before your trip to Chicago. The lowest price found when booking 68 days ahead was $112 per night.

Find deals

Cheapest holiday rentals in Chicago, Illinois

Discover affordable stays in Chicago that provide a quality experience without breaking the bank. Hotels in Chicago can be found for as low as $179 per night. There is currently one property in Chicago that can be booked for this price. Level Chicago - Old Town is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 13 March 2026
At the moment, these vacation rentals offer the lowest nightly rate out of those we've come across in Chicago. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
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
$179
Avg. per night
View Deal
The Greenleaf House
The Greenleaf House

The Greenleaf House

Chicago, IL, United States
15.3 km from city centre
Air conditioning
Free Wi-Fi
$549
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,735 hotels in Chicago and price data was last updated on 13 March 2026. The average price for a hotel in Chicago is $325/night.
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
$156
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
$201
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
$175
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
$58
Avg. per night
View Deal

Where to stay in Chicago

Explore different neighbourhoods and areas within Chicago to find the perfect location for your stay. Map data was last updated on 13 March 2026.
Navigate to the areas in Chicago you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation rental within the map by clicking on its name.

Facts about staying in Chicago

Find useful tips and insights about staying in Chicago to help you make the most of your experience. FAQs were last updated on 13 March 2026.

  • How much does a holiday rental in Chicago cost?

    The average cost for a holiday rental in Chicago is $325/night. A good holiday rental deal in Chicago would be for $217/night or less. The cheapest rental deal found recently by our users was $25/night. If you’re flexible with your travel dates, then try to avoid booking March, the most expensive month of the year. Booking March is the cheapest month to book a holiday rental in Chicago.

  • What is the best Chicago holiday rental?

    Hotel 55 Chicago Downtown has a 8.3 rating from 1,122 users, making it the best Chicago holiday rental based on our data.

  • 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 Chicago Loop Synagogue?

    While there may be several Chicago holiday rentals near Chicago Loop Synagogue, 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 1,122 HotelsCombined travellers. Chicago Loop Synagogue is also conveniently located just 1.4 km from this holiday rental.

  • Are there any Motel holiday rentals in Chicago?

    Yes, there are 34 Motel holiday rentals in Chicago. According to our data, Ohio House Motel is currently the most popular Motel rental in the city.

See more FAQs

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