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Vacation rentals in Chicago, IL

Search and compare Chicago, IL vacation rentals from hundreds of travel sites and save.

Chicago, United States
Nov 27 — Nov 282
...and more

Tips for booking vacation rentals in Chicago

Gain useful insights and advice for booking the perfect stay in Chicago. Price data is based on averages over the past 12 months and was last updated on November 20, 2024.
Cheapest month:March
Most expensive month:April
Average price in Chicago:$224/night
Cheapest price found:$6/night
Cheapest day:Tuesday
Most expensive day:Saturday
$124 - $558
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$188 - $275
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 3,041 hotels in Chicago and price data was last updated on November 20, 2024. The average price for a hotel in Chicago is $224/night.
Show all 3,041 stays
Chicago Getaway Hostel
Chicago Getaway Hostel
Chicago Getaway Hostel
616 West Arlington Place, Chicago, IL, United States
3.6 mi from city centre
Free Wi-Fi
$43
Avg. per night
View Deal
Wrigley Hostel
Wrigley Hostel
Wrigley Hostel
3514 North Sheffield Avenue, Chicago, IL, United States
5.0 mi from city centre
Free Wi-Fi
Parking
$36
Avg. per night
View Deal
Warwick Allerton Chicago
Warwick Allerton Chicago
Warwick Allerton Chicago
701 North Michigan Avenue, Chicago, IL, United States
1.3 mi from city centre
Free Wi-Fi
$108
Avg. per night
View Deal
Hilton Chicago
Hilton Chicago
Hilton Chicago
720 South Michigan Avenue, Chicago, IL, United States
0.3 mi from city centre
Free Wi-Fi
$144
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
$424
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 20, 2024.
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 20, 2024.

  • How much does a vacation rental in Chicago cost?

    $224 per night is how much a vacation rental in Chicago costs, on average. $7 per night was the cheapest price recently found by our users, though anything for $173 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 April, and the cheapest time to book is January.

  • 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 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena - the neighborhood’s most popular rental property.

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