Chicago Holiday Rentals

Find the best deals on 1,334 holiday rentals in Chicago

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Top rentals in Chicago

Find the perfect Chicago holiday rental for your needs
The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.4
£117
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River North Waterside Condos
River North Waterside Condos
£106
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Stay Alfred At The Seneca
Stay Alfred At The Seneca
£106
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Nice In Law Apartment, Close To O'hare Airport In Chicago
Nice In Law Apartment, Close To O'hare Airport In Chicago
£74
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Ultra Luxury 3br In South Loop W/ Pool & Spa By Domio
Ultra Luxury 3br In South Loop W/ Pool & Spa By Domio
8.6
£324
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The Avondale Guesthouse
The Avondale Guesthouse
9.3
£64
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Forrestville Ave Large Suite
Forrestville Ave Large Suite
8.7
£57
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Ginosi 747 Apartel
Ginosi 747 Apartel
£55
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Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
£100
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Bright 2BR in Bucktown by Sonder
Bright 2BR in Bucktown by Sonder
£157
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Beautiful Room in Chicago
Beautiful Room in Chicago
7.1
£49
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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
February
High season
October

cheapest month to stay

76%

expected price decrease

most expensive time to stay

65%

expected price increase

Price
£46 - £520
Highest day of week
Thursday
Cheapest day of week
Monday

avg. price over the last two weeks

Average price (weeknight)

£125

avg. price over the last two weeks

avg. price over the last two weeks

Average price (weekend night)

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
Ginosi 747 Apartel
Ginosi 747 Apartel
£55
Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
£100
Forrestville Ave Large Suite
Forrestville Ave Large Suite
8.7
£57
River North Waterside Condos
River North Waterside Condos
£106
The Avondale Guesthouse
The Avondale Guesthouse
9.3
£64
The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.4
£117

Chicago holiday apartments & rental properties FAQ

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

Those choosing holiday rental apartments in Chicago typically book for at least 6 nights.

How much does a holiday rental apartment in Chicago cost?

Around £142 per night is the typical cost of a holiday apartment in Chicago - note that if you are booking an apartment for a larger group or require more rooms and facilities in your rental, the price will likely be higher.

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

Chicago holiday rentals are at their cheapest in February. Rental prices can be around 76% lower per night than in the high season.

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

Near West Side is the most popular area of Chicago to book a rental apartment in. Near South Side and Logan Square are also sought-after places to stay.