Chicago Holiday Rentals

Find the best deals on 1,644 holiday rentals in Chicago

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Top rentals in Chicago

Find the perfect Chicago holiday rental for your needs
High Rise w/ Gym Pool & Jacuzzi
High Rise w/ Gym Pool & Jacuzzi
£97
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The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.3
£186
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Private Room #2, near O'Hare airport,
Private Room #2, near O'Hare airport,
£32
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Steps Away From Mca Chicago
Steps Away From Mca Chicago
£86
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Lux 2B/1B Panoramic Views
Lux 2B/1B Panoramic Views
£206
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Stay Alfred At The Seneca
Stay Alfred At The Seneca
£103
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Neat Condo | 7 min to Wrigley | Cubs | Netflix CL2
Neat Condo | 7 min to Wrigley | Cubs | Netflix CL2
£49
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River North Waterside Condos
River North Waterside Condos
£160
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Beautiful Room in Chicago
Beautiful Room in Chicago
7.1
£63
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Beautiful first floor walk up on quiet street
Beautiful first floor walk up on quiet street
9.6
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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
£73
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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
£314
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Millennium Park River King Bed
Millennium Park River King Bed
£98
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Smart 2BR near Restaurant Row by Sonder
Smart 2BR near Restaurant Row by Sonder
£150
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Bright 2BR in Bucktown by Sonder
Bright 2BR in Bucktown by Sonder
£152
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Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
£97
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Ginosi 747 Apartel
Ginosi 747 Apartel
£54
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Forrestville Ave Large Suite
Forrestville Ave Large Suite
8.7
£76
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Wriggleyville Studio W/ Balcony
Wriggleyville Studio W/ Balcony
£55
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Quaint & Cozy Southside Guest Rm; Near Transit, U. Chicago, Historic Bronzeville
Quaint & Cozy Southside Guest Rm; Near Transit, U. Chicago, Historic Bronzeville
£117
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The Avondale Guesthouse
The Avondale Guesthouse
9.4
£90
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Right Downtown near Millennium Park
Right Downtown near Millennium 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
February
High season
December

cheapest month to stay

69%

expected price decrease

most expensive time to stay

54%

expected price increase

Price
£44 - £302
Highest day of week
Friday
Cheapest day of week
Sunday

avg. price over the last two weeks

Average price (weeknight)

£230

avg. price over the last two weeks

avg. price over the last two weeks

Average price (weekend night)

£171

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
£54
The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.3
£186
Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
£97
River North Waterside Condos
River North Waterside Condos
£160

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 £233 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 69% lower per night than in the high season.

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

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