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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 May ($73). Conversely, the most expensive month to stay in Chicago is March ($1,679).

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

The cheapest day to stay in Chicago is Thursday ($186). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $471.

Which Chicago neighborhoods are most popular to stay in?

Those visiting Chicago tend to stay in Chinatown, where a vacation rental costs around $461/night. Another popular neighborhood in Chicago is Pilsen, which is $38/night on average for a vacation rental.

How early should you book a vacation rental in Chicago?

Based on vacation rental prices in Chicago found by KAYAK users over the last 12 months.

Book at least 50 days before your stay begins to get the best price for your Chicago vacation rental.

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 $69 per night. There is currently one property in Chicago that can be booked for this price. The Greenleaf House is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on August 17, 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.
The Greenleaf House
The Greenleaf House

The Greenleaf House

1320 West Greenleaf Avenue, Chicago, IL, United States
9.5 mi from city centre
Free Wi-Fi
Air Conditioning
$69
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
1.2 mi from city centre
Free Wi-Fi
$188
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
1.9 mi from city centre
Free Wi-Fi
$268
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 2,565 hotels in Chicago and price data was last updated on August 17, 2026. The average price for a hotel in Chicago is $417/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
1.0 mi from city centre
Pool
Free Wi-Fi
$259
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
$253
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
$639
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
$68
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
$73
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 August 17, 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 August 17, 2026.

  • How much does a vacation rental in Chicago cost?

    $260 per night is how much a vacation rental in Chicago costs, on average. $16 per night was the cheapest price recently found by our users, though anything for $201 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 November, and the cheapest time to book is August.

  • What is the best Chicago vacation rental?

    Level Chicago - Old Town has a 9.2 rating from 341 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 1,119 users. The distance from Aon Center to Hotel 55 Chicago Downtown is 0.6 mi.

  • Are there Chicago vacation rentals with “Pool” listed as an amenity?

    1 vacation rental in Chicago currently mentions “Pool” as a listed amenity. We recommend booking the Level Chicago - Old Town, which is the most popular Chicago vacation rental featuring this amenity.

See more FAQs

Find better results for your stay in Chicago

Consider other places to stay in Chicago

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