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Vacation rentals in Chicago

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Travel insights for vacation rentals in Chicago

Use our HotelsCombined data-powered tips to help you find your next vacation 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 January ($109). Conversely, the most expensive month to stay in Chicago is September ($465).

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

The cheapest day to stay in Chicago is Sunday ($199). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $430.

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 $106 per night.
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Cheapest vacation 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 $189 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 November 18, 2025
These are the lowest prices we've found on vacation rentals in Chicago at the moment. If you have the flexibility, change the dates selected to compare prices.
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
$189
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 2,523 hotels in Chicago and price data was last updated on November 18, 2025. The average price for a hotel in Chicago is $239/night.
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
$52
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
$44
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
$128
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
$156
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
1.5 mi from city centre
Pool
Free Wi-Fi
$334
Avg. per night
View Deal

Where to stay in Chicago

Explore different neighborhoods and areas within Chicago to find the perfect location for your stay. Map data was last updated on November 18, 2025.
Use the map to find vacation rentals in Chicago that are close to the points of interest you'll be frequenting. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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 November 18, 2025.

  • How much does a vacation rental in Chicago cost?

    $239 per night is how much a vacation rental in Chicago costs, on average. $12 per night was the cheapest price recently found by our users, though anything for $175 per night or less is a good deal. Keep in mind that Chicago vacation rental prices fluctuate throughout the year: the most expensive month to book is October, and the cheapest time to book is October.

  • What’s the closest vacation rental to Chicago O'Hare Intl Airport?

    It’s only 12.5 mi from Chicago O'Hare Intl Airport to The Greenleaf House (the nearest Chicago vacation rental to the airport).

  • What part of Chicago is best to stay in?

    The best neighborhood to stay in Chicago is Downtown, according to our user data. 0% of our users who looked for vacation rentals in Chicago searched for properties in the Downtown area. If you’re also interested in booking a vacation rental in Downtown, consider the 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown - the neighborhood’s most popular rental property.

Find better results for your stay in Chicago

Consider other places to stay in Chicago

Stay at one of these places that users have found on HotelsCombined.
Chicago Bed & Breakfasts
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