Illinois holiday rentals

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Best Illinois holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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RM 188 - RM 852RM 852 - RM 1,511RM 1,511 - RM 2,170RM 2,170 - RM 2,834RM 2,834+ per night

Property type

ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Illinois

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Close to Downtown - Free Parking - Chicago
Close to Downtown - Free Parking
South Side
7.6Good(4)
Homestay
Parking
Free Wi-Fi
RM 221+
Check availability
Econo Lodge Rockford Casino Area - Rockford - Bedroom
Econo Lodge Rockford Casino Area
Rockford, IL, United States
7.7Good(230)
Lodge
Parking
Free Wi-Fi
Pet-friendly
RM 254+
Check availability
Homestay - Cozy House -- Friendly Family - Champaign
Homestay - Cozy House -- Friendly Family
Champaign, IL, United States
Homestay
RM 262+
Check availability
Drexel Apartments, Downtown Hyde Park - Chicago
Drexel Apartments, Downtown Hyde Park
South Side
6.5Okay(62)
Homestay
Parking
Free Wi-Fi
RM 353+
Check availability
Exquisite Victorian - Springfield
Exquisite Victorian
Springfield, IL, United States
9.8Wonderful(159)
Homestay
Parking
Free Wi-Fi
Pet-friendly
RM 356+
Check availability
Kenwood Apartments, Downtown Hyde Park - Chicago
Kenwood Apartments, Downtown Hyde Park
South Side
6.0Okay(39)
Homestay
Parking
Free Wi-Fi
RM 394+
Check availability
5430 Happy Home - Chicago
5430 Happy Home
South Side
8.0Very Good(323)
Homestay
Parking
Free Wi-Fi
RM 553+
Check availability
Global Luxury Suites at the Chicago Loop - Chicago
Global Luxury Suites at the Chicago Loop
Downtown
8.9Very Good(30)
Apartment
Free Wi-Fi
RM 663+
Check availability
Wonderful Home Close to Downtown Chicago - Free Parking - Chicago
Wonderful Home Close to Downtown Chicago - Free Parking
South Side
9.1Wonderful(5)
Homestay
Parking
Free Wi-Fi
RM 729+
Check availability
Entire Modern 2 Bedroom Apartment - Chicago
Entire Modern 2 Bedroom Apartment
Belmont Cragin
6.8Okay(12)
Apartment
Free Wi-Fi
RM 761+
Check availability
5 acre Paradise-Shawnee Wine Trail, Pool, Pond, Firepit, Pet Friendly - Carbondale - Bedroom
5 acre Paradise-Shawnee Wine Trail, Pool, Pond, Firepit, Pet Friendly
Carbondale, IL, United States
9.9Wonderful(20)
Cottage
RM 794+
Check availability
Beautiful Big 3 bedroom Quiet Apt near downtown - Chicago
Beautiful Big 3 bedroom Quiet Apt near downtown
South Side
8.3Very Good(17)
Apartment
Parking
Free Wi-Fi
RM 933+
Check availability
Just Minutes from Downtown Chicago - Chicago - Bedroom
Just Minutes from Downtown Chicago
South Side
9.3Wonderful(6)
House
RM 1,018+
Check availability
Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena - Chicago
Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
Near South Side
8.9Very Good(155)
Apartment
Free Wi-Fi
Pet-friendly
RM 1,128+
Check availability
Luxury Log Cabin w/ Hot Tub Near Carbondale - Carbondale - Living room
Luxury Log Cabin w/ Hot Tub Near Carbondale
Carbondale, IL, United States
9.8Wonderful(37)
Cabin
Free Wi-Fi
RM 1,765+
Check availability
Ginosi Chicago Apartel - Chicago
Ginosi Chicago Apartel
Near North Side
Apartment
RM 2,158+
Check availability
Booking Insights

KAYAK’s insights for holiday rentals in Illinois

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Illinois with confidence.

How early should you book a vacation rental in Illinois?

Book at least 37 days before your stay begins to get the best price for your Illinois vacation rental.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
February
RM 1,097
RM 913
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 169% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Illinois holiday rental

  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Illinois for 6 days.
  • Pool, hot tub, parking, and pet friendly are the most popular holiday rental property amenities in Illinois
  • Holiday rentals in Illinois are around 27% more expensive than hotels on average. Search here to compare prices for all accommodation types in Illinois.
  • The city in Illinois with the most affordable holiday homes is Chicago, with around 1,995 properties and an average price of RM 188. The most popular holiday rentals in Illinois among KAYAK users are 5430 Happy Home, Ginosi Chicago Apartel, and Drexel Apartments, Downtown Hyde Park.

FAQs when booking a holiday home in Illinois

  • What is the most popular holiday rental destination in Illinois?

    Based on KAYAK holiday rental searches, the most popular destination is Chicago (100% of total searches to Illinois).

  • How much is a holiday rental in Illinois for tonight?

    In the last 72 hours, users have found Illinois holiday rentals for tonight for as little as RM 285. Search here for similar prices

  • How much is a holiday rental in Illinois for this weekend?

    In the last 72 hours, users have found Illinois holiday rentals for this weekend for as little as RM 331 per night. Search here for similar prices

  • How much is a holiday rental for a week in Illinois?

    The average price for a weekly Illinois holiday rental found by KAYAK users in the last 2 weeks is RM 1,319.

  • How much is a holiday rental for a month in Illinois?

    The average price for a monthly Illinois holiday rental found by KAYAK users in the last 2 weeks is RM 5,653.

  • What types of holiday rentals are available in Illinois?

    There are loads of different property types that you can make your holiday home in Illinois. You’ll find apartments, houses, hotels, condos, homestays, cottages, lodges, villas, cabins, caravans, agritourism, bed & breakfasts, chalets and motels.

  • Are there any pet-friendly holiday rentals in Illinois?

    There are a number of dog and pet-friendly Illinois holiday rentals, with around 7% allowing you to bring your pet along with you.

Where to stay in Illinois?

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

Everything you need to know for your stay in Illinois

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