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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 month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is April ($242). Conversely, the most expensive month to stay in Chicago is October ($688).

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

The cheapest day to stay in Chicago is Sunday ($325). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $581.

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

Save money by booking a vacation rental at least 79 days before your trip to Chicago. The lowest price found when booking 79 days ahead was $139 per night.

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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 $395 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 18 April 2026
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.
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
$395
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
$1,137
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,635 hotels in Chicago and price data was last updated on 18 April 2026. The average price for a hotel in Chicago is $383/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
$322
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
$406
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
$334
Avg. per night
View Deal
The Golden Arm
The Golden Arm

The Golden Arm

1745 W Division St, Chicago, IL, United States
4.8 km from city centre
Free Wi-Fi
Air conditioning
$248
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 18 April 2026.
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

Find useful tips and insights about staying in Chicago to help you make the most of your experience. FAQs were last updated on 18 April 2026.

  • How much does a holiday rental in Chicago cost?

    $383/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that December is the most expensive month to book, and June is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $18/night. In general, any Chicago rental for $280 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 1,126 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 1,126 reviews, Hotel 55 Chicago Downtown is the most popular holiday rental in Chicago that’s close to Magnificent Mile (just 0.2 km away).

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