Illinois holiday rentals

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Best Illinois holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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€34 - €175€175 - €317€317 - €459€459 - €600€600+ per night

Property type

ApartmentCondoHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Illinois

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Econo Lodge - Marion - Building
Econo Lodge
Marion, IL, United States
4.9Mediocre(308)
Lodge
Pool
Pet friendly
€44+
Check availability
Close to Downtown - Free Parking - Chicago
Close to Downtown - Free Parking
South Side
7.8Good(4)
Homestay
Parking
Free Wi-Fi
Air conditioning
€46+
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Homestay - Cozy Garden Apartment - Chicago
Homestay - Cozy Garden Apartment
South Side
Homestay
€64+
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Exquisite Victorian - Springfield
Exquisite Victorian
Springfield, IL, United States
9.8Wonderful(159)
Homestay
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€75+
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Drexel Apartments, Downtown Hyde Park - Chicago
Drexel Apartments, Downtown Hyde Park
South Side
6.5Okay(62)
Homestay
Parking
Free Wi-Fi
Air conditioning
€75+
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Kenwood Apartments, Downtown Hyde Park - Chicago
Kenwood Apartments, Downtown Hyde Park
South Side
5.9Fair(39)
Homestay
Parking
Free Wi-Fi
Air conditioning
€84+
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5430 Happy Home - Chicago
5430 Happy Home
South Side
8.1Very Good(323)
Homestay
Parking
Free Wi-Fi
Air conditioning
€126+
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The Avondale Attic - Chicago - Building
The Avondale Attic
Irving Park
9.5Wonderful(14)
Apartment
Parking
Free Wi-Fi
Air conditioning
€138+
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Global Luxury Suites at the Chicago Loop - Chicago
Global Luxury Suites at the Chicago Loop
Downtown
8.9Very Good(30)
Apartment
Free Wi-Fi
Air conditioning
€139+
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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
Air conditioning
€153+
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Entire Modern 2 Bedroom Apartment - Chicago
Entire Modern 2 Bedroom Apartment
Belmont Cragin
6.8Okay(12)
Apartment
Free Wi-Fi
Air conditioning
€174+
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Beautiful Big 3 bedroom Quiet Apt near downtown - Chicago
Beautiful Big 3 bedroom Quiet Apt near downtown
South Side
8.7Very Good(17)
Apartment
Parking
Free Wi-Fi
Air conditioning
€199+
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Just Minutes from Downtown Chicago - Chicago - Bedroom
Just Minutes from Downtown Chicago
South Side
9.3Wonderful(6)
House
Air conditioning
€212+
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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(153)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€234+
Check availability
Fulbrix Bright Designer Apartments with West Loop Views - Chicago - Dining room
Fulbrix Bright Designer Apartments with West Loop Views
Near West Side
9.3Wonderful(21)
Apartment
Free Wi-Fi
Pool
Pet friendly
Air conditioning
€433+
Check availability
Ginosi Chicago Apartel - Chicago
Ginosi Chicago Apartel
Near North Side
Apartment
€453+
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)

December
February
€200
€230
Cheapest month to stay with an average 48% drop in price.
Most expensive month to stay with an average 388% 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

  • If you’re looking for a cheap holiday rental in Illinois, you should consider visiting during the low season. The cheapest holiday homes in Illinois can be found in May and June.
  • The cheapest night for renting a holiday home in Illinois is Wednesday. In contrast, the most expensive is Tuesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Illinois for 1 days.
  • Pool, hot tub, parking, and pet friendly are the most popular holiday rental property amenities in Illinois
  • Holiday rentals in Illinois are around 16% more expensive than hotels on average. Search here to compare prices for all accommodation types in Illinois.

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 €60. 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 €69 per night. Search here for similar prices

  • 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 houses, apartments, condos, homestays, cottages, lodges, villas, cabins, caravans, agritourism, bed & breakfasts, chalets and hotels.

  • 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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