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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 April ($142). Conversely, the most expensive month to stay in Chicago is August ($451).

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

The cheapest day to stay in Chicago is Sunday ($191). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $378.

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 $82 per night.

Find deals

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 $224 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 April 16, 2026
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
$224
Avg. per night
View Deal
The Greenleaf House
The Greenleaf House

The Greenleaf House

Chicago, IL, United States
9.5 mi from city centre
Air Conditioning
Free Wi-Fi
$670
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 2,624 hotels in Chicago and price data was last updated on April 16, 2026. The average price for a hotel in Chicago is $236/night.
The Golden Arm
The Golden Arm

The Golden Arm

1745 W Division St, Chicago, IL, United States
3.0 mi from city centre
Free Wi-Fi
Air Conditioning
$148
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
$181
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
$194
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
$514
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
$60
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$54
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
$60
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 April 16, 2026.
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 April 16, 2026.

  • How much does a vacation rental in Chicago cost?

    $237 per night is how much a vacation rental in Chicago costs, on average. $11 per night was the cheapest price recently found by our users, though anything for $167 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 December, and the cheapest time to book is June.

  • What is the best Chicago vacation rental?

    Hotel 55 Chicago Downtown has a 8.3 rating from 1,127 users, making it the best Chicago vacation rental based on our data.

  • 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’s the most popular vacation rental in Chicago near Aon Center?

    If you’re looking for a vacation rental close to Aon Center while in Chicago, then the most popular is Hotel 55 Chicago Downtown with a 8.3/10 review score from 1,127 users. The distance from Aon Center to Hotel 55 Chicago Downtown is 0.6 mi.

See more FAQs

Find better results for your stay in Chicago

Consider other places to stay in Chicago

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