Illinois holiday rentals

Search hundreds of travel sites at once for car rental deals in Illinois

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Latest Illinois holiday rental deals

MOST POPULARChicago
Holiday homes from £187

Best Illinois holiday rentals

Casa 22 • Luxury Modern House for 6 • 3 Bed, 2 Bath - Skokie - Dining room
Casa 22 • Luxury Modern House for 6 • 3 Bed, 2 Bath
Skokie, IL, United States
10Wonderful(10)
House
Free Wi-Fi
Air conditioning
£400+
Check availability
Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house - Skokie - Living room
Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house
Skokie, IL, United States
9.3Wonderful(3)
House
Pool
Air conditioning
£831+
Check availability
Home Away From Home - Skokie - Bedroom
Home Away From Home
Skokie, IL, United States
8.5Very Good(10)
House
Parking
Free Wi-Fi
Air conditioning
£180+
Check availability
Home w/ Fenced Yard: 13 Mi to Downtown Chicago! - Evanston - Living room
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Evanston, IL, United States
7.4Good(7)
House
Air conditioning
£155+
Check availability
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover - Evanston - Living room
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
Evanston, IL, United States
8.1Very Good(11)
Apartment
Air conditioning
£171+
Check availability
Lovely 3 Bedroom Apartment with ample street parking - Skokie - Dining room
Lovely 3 Bedroom Apartment with ample street parking
Skokie, IL, United States
Apartment
Air conditioning
£94+
Check availability
Culinary Dream - Tranquil Home - Pizza Oven/Bbq/Smoker - Skokie - Living room
Culinary Dream - Tranquil Home - Pizza Oven/Bbq/Smoker
Skokie, IL, United States
9.6Wonderful(5)
House
Air conditioning
£508+
Check availability
Stunning downtown Skokie mid-century modern Luxury four bedroom ranch home - Skokie - Dining room
Stunning downtown Skokie mid-century modern Luxury four bedroom ranch home
Skokie, IL, United States
House
Air conditioning
£496+
Check availability
Bright and Cozy 1BR Apartment in Logan Square! - Chicago - Living room
Bright and Cozy 1BR Apartment in Logan Square!
Logan Square
9.9Wonderful(28)
Apartment
Free Wi-Fi
Air conditioning
£97+
Check availability
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome - Chicago - Patio
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome
Near North Side
9.6Wonderful(74)
House
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£569+
Check availability
5 Bedroom Huge House in Best Location Parking Fireplace Back Yard - Chicago - Living room
5 Bedroom Huge House in Best Location Parking Fireplace Back Yard
Near North Side
9.3Wonderful(75)
House
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£453+
Check availability
Walk to Train Convenient Skokie Condo! - Skokie
Walk to Train Convenient Skokie Condo!
Skokie, IL, United States
7.0Good(2)
Condo
Air conditioning
£150+
Check availability
Exquisite Victorian - Springfield
Exquisite Victorian
Springfield, IL, United States
9.8Wonderful(166)
Homestay
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£65+
Check availability
Walk to Train Convenient Skokie Condo! - Skokie
Walk to Train Convenient Skokie Condo!
Skokie, IL, United States
5.0Fair(1)
Apartment
Free Wi-Fi
Air conditioning
£141+
Check availability
Home with Fenced Yard 13 Mi to Downtown Chicago! - Evanston
Home with Fenced Yard 13 Mi to Downtown Chicago!
Evanston, IL, United States
4.0Mediocre(1)
House
Free Wi-Fi
Pet-friendly
Air conditioning
£144+
Check availability
K2 Sky High Apartments with Stunning Chicago Views in West Loop - Chicago
K2 Sky High Apartments with Stunning Chicago Views in West Loop
Near West Side
9.5Wonderful(17)
Apartment
Free Wi-Fi
Pool
Air conditioning
£353+
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 68 days before your stay begins to get the best price for your Illinois vacation rental.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
August
£189
£185
Cheapest month to stay with an average 41% drop in price.
Most expensive month to stay with an average 333% 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 Tuesday. In contrast, the most expensive is Wednesday.
  • 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 35% 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 1,920 properties and an average price of £139. The most popular holiday rentals in Illinois among KAYAK users are Bright and Cozy 1BR Apartment in Logan Square!, K2 Sky High Apartments with Stunning Chicago Views in West Loop, and 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome.

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 (74% of total searches to Illinois). The next most popular destinations are Kankakee (16%) and Michael (5%). Searches for holiday rentals in Litchfield (5%) are also popular.

  • 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 £49. 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 £972.

  • 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 £4,166.

  • 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, cottages, cabins, campgrounds, condos, villas, bungalows, homestays, lodges, caravans, agritourism, bed & breakfasts, chalets and castles.

  • What are some of the most-loved holiday rentals available in Illinois?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Econo Lodge Quincy.

  • 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