Chicago Metropolitan Area holiday rentals

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Best Chicago Metropolitan Area holiday rentals

Most recommended holiday rentals in Chicago Metropolitan Area

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10-15 Min From O'hare Chicago-Lovely 3bedrooms Garden Apartment - Franklin Park - Bedroom
10-15 Min From O'hare Chicago-Lovely 3bedrooms Garden Apartment
Franklin Park, IL, United States
Free Wi-Fi
$377+
View availability
Luxe 3br, 2ba + Hot Tub - Elmhurst - Living room
Luxe 3br, 2ba + Hot Tub
Elmhurst, IL, United States
8.7Very Good(15)
Parking
Free Wi-Fi
Pet-friendly
$606+
View availability
The Tailor House - Woodstock - Living room
The Tailor House
Woodstock, IL, United States
Free Wi-Fi
$568+
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1-Bedroom Nice Apartment in Skokie - Skokie - Living room
1-Bedroom Nice Apartment in Skokie
Skokie, IL, United States
$365+
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Pet-Friendly Family Apartment - Near Nu Campus! - Evanston - Living room
Pet-Friendly Family Apartment - Near Nu Campus!
Evanston, IL, United States
9.6Wonderful(25)
Free Wi-Fi
Pet-friendly
$582+
View availability
Simple and Roomy 1BR Apt in Evanston - Evanston - Building
Simple and Roomy 1BR Apt in Evanston
Evanston, IL, United States
2.0Poor(2)
$389+
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Family Apartment with Deck and Yard Near Northwestern - Evanston - Living room
Family Apartment with Deck and Yard Near Northwestern
Evanston, IL, United States
9.6Wonderful(16)
Free Wi-Fi
$466+
View availability
Bright and Charming 2 Bed Apartment in Evanston by AllSet Turnover - Evanston - Living room
Bright and Charming 2 Bed Apartment in Evanston by AllSet Turnover
Evanston, IL, United States
Free Wi-Fi
$507+
View availability
6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park - Marengo - Building
6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park
Marengo, IL, United States
Free Wi-Fi
$3,052+
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Luxe Haus Of Love—Renovated 1938 Cape Cod |heated Flrs |420+ - Skokie - Living room
Luxe Haus Of Love—Renovated 1938 Cape Cod |heated Flrs |420+
Skokie, IL, United States
$1,159+
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Walk to Train Convenient Skokie Condo! - Skokie - Kitchen
Walk to Train Convenient Skokie Condo!
Skokie, IL, United States
Free Wi-Fi
$323+
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Adorable 1BR Apartment in Evanston - Evanston - Living room
Adorable 1BR Apartment in Evanston
Evanston, IL, United States
$440+
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Perfect Location Near Ohare Lcp Collection - Melrose Park
Perfect Location Near Ohare Lcp Collection
Melrose Park, IL, United States
Parking
Free Wi-Fi
$1,050+
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Top Notch Golf Getaway, Family Reunion or Forum Retreat - Woodstock
Top Notch Golf Getaway, Family Reunion or Forum Retreat
Woodstock, IL, United States
$1,783+
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Elevated Stay 3BR in Addison - Addison
Elevated Stay 3BR in Addison
Addison, IL, United States
Parking
Free Wi-Fi
Pet-friendly
$864+
View availability
Stunning home in Skokie - Skokie
Stunning home in Skokie
Skokie, IL, United States
10Wonderful(1)
Parking
Free Wi-Fi
Pet-friendly
$1,010+
View availability
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$69 - $612$612 - $1,154$1,154 - $1,696$1,696 - $2,237$2,237+ per night

Property type

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Good to know

Low season

January

High season

August

Average price (weeknight)

$370

Average price (weekend night)

$416
Cheapest month to stay with an average 21% drop in price.
Most expensive month to stay with an average 68% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a holiday home in Chicago Metropolitan Area

  • How much is a holiday rental in Chicago Metropolitan Area for tonight?

    In the last 72 hours, users have found Chicago Metropolitan Area holiday rentals for tonight for as little as $125. Search here for similar prices

  • What types of holiday rentals are available in Chicago Metropolitan Area?

    There are loads of different property types that you can make your holiday home in Chicago Metropolitan Area. You’ll find apartments, houses, lodges, condos, cabins, cottages, homestays, villas, agritourism, campgrounds, caravan parks and chalets.

  • Are there any pet-friendly holiday rentals in Chicago Metropolitan Area?

    There are a number of dog and pet-friendly Chicago Metropolitan Area holiday rentals, with around 15% allowing you to bring your pet along with you.

Where to stay in Chicago Metropolitan Area?

Our map will help you find the perfect place to stay in Chicago Metropolitan Area by showing you the exact location of each holiday home.

Everything you need to know for your stay in Chicago Metropolitan Area

Holiday rentals in Chicago Metropolitan Area

Chicago holiday rentals

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