Chicago Holiday Rentals

Find the best deals on 1,932 holiday rentals in Chicago

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Top rentals in Chicago

Find the perfect Chicago holiday rental for your needs
Distinct Lincoln Park Suites by Sonder
Distinct Lincoln Park Suites by Sonder
$184
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Downtown Lincoln Park Abode With Private Entrance
Downtown Lincoln Park Abode With Private Entrance
$197
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Literally 1 min to Millenium Park
Literally 1 min to Millenium Park
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When to book a holiday apartment in Chicago

Check out the tips below to find the best deal on a Chicago holiday rental property
Low season
December
High season
October

cheapest month to stay

57%

expected price decrease

most expensive time to stay

45%

expected price increase

Price
$76 - $315
Highest day of week
Friday
Cheapest day of week
Sunday

avg. price over the last two weeks

Average price (weeknight)

$600

avg. price over the last two weeks

avg. price over the last two weeks

Average price (weekend night)

$443

avg. price over the last two weeks


Cheapest holiday rentals in Chicago

Our lowest-priced holiday apartments and property rentals for a cheaper way to stay in Chicago
Distinct Lincoln Park Suites by Sonder
Distinct Lincoln Park Suites by Sonder
$184

Chicago holiday apartments & rental properties FAQ

How long do people typically book holiday apartments for in Chicago?

About 4 nights is the most common choice for those booking holiday apartment rentals in Chicago.

When is the best time to book a holiday rental in Chicago?

December is typically when Chicago holiday apartment and rental property prices are at their lowest, with prices around 57% lower than the Chicago peak season.

What’s the best area of Chicago to book a holiday rental in?

The most popular areas to book Chicago holiday rentals in are Grand Boulevard, Lincoln Park, and Lake View.