Illinois vacation rentals

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Booking Insights
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Latest Illinois vacation rental deals

MOST POPULARChicago
Vacation homes from C$ 12

Best Illinois vacation rentals

Bright and Cozy 1BR Apartment in Logan Square! - Chicago - Living room
Bright and Cozy 1BR Apartment in Logan Square!
Logan Square
9.9Wonderful(29)
Apartment
Free Wi-Fi
C$ 186+
Check availability
Historic Luxury Townhouse In Downtown Ch - Chicago - Bedroom
Historic Luxury Townhouse In Downtown Ch
Near North Side
9.2Wonderful(68)
House
C$ 731+
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(75)
House
Parking
Free Wi-Fi
Pet friendly
C$ 1,051+
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(76)
House
Parking
Free Wi-Fi
Pet friendly
C$ 847+
Check availability
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover - Chicago - Building
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Andersonville
8.8Very good(18)
Condo
C$ 355+
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Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover - Chicago - Living room
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
North Center
9.2Wonderful(11)
Apartment
C$ 414+
Check availability
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover - Chicago - Living room
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover
North Center
9.2Wonderful(8)
Apartment
C$ 460+
Check availability
New Listing! Modern Design 2bd Garden Condo Near United Center By Allset Turnover - Chicago - Living room
New Listing! Modern Design 2bd Garden Condo Near United Center By Allset Turnover
Near West Side
9.0Wonderful(2)
Condo
C$ 459+
Check availability
Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover - Chicago - Living room
Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover
Lower West Side
10Wonderful(1)
Apartment
C$ 334+
Check availability
Breathtaking & Bright: Designer 2BD with Garage - Chicago - Living room
Breathtaking & Bright: Designer 2BD with Garage
Near West Side
10Wonderful(2)
Apartment
C$ 384+
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Spacious Luxury Townhouse - Old Town by AllSet Turnover - Chicago - Living room
Spacious Luxury Townhouse - Old Town by AllSet Turnover
Lincoln Park
8.4Very good(10)
House
C$ 721+
Check availability
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover - Chicago - Living room
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Edgewater
9.8Wonderful(35)
Condo
C$ 640+
Check availability
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover - Chicago - Kitchen
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover
North Lawndale
9.6Wonderful(6)
Apartment
C$ 503+
Check availability
Inviting Stylish Home with Covered Patio - Chicago - Living room
Inviting Stylish Home with Covered Patio
Uptown
9.0Wonderful(10)
House
Free Wi-Fi
C$ 402+
Check availability
Perfect place to enjoy the city or just relax - Chicago
Perfect place to enjoy the city or just relax
North Lawndale
8.2Very good(149)
Apartment
Parking
Free Wi-Fi
C$ 232+
Check availability
Indulging 2BR Apartment in Festive Boystown - Buckingham 1 - Chicago
Indulging 2BR Apartment in Festive Boystown - Buckingham 1
Lake View
9.4Wonderful(4)
Apartment
Free Wi-Fi
Pet friendly
C$ 275+
Check availability
Booking Insights

KAYAK’s insights for vacation 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)

February
August
C$ 280
C$ 372
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 376% 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 vacation rental

  • If you’re looking for a cheap vacation rental in Illinois, you should consider visiting during the low season. The cheapest vacation homes in Illinois can be found in December and July.
  • The cheapest night for renting a vacation home in Illinois is Monday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Illinois for 1 days.
  • Pool, hot tub, parking, and pet friendly are the most popular vacation rental property amenities in Illinois
  • Vacation rentals in Illinois are around 33% more expensive than hotels on average. Search here to compare prices for all accommodation types in Illinois.

FAQs when booking a vacation home in Illinois

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

    Based on KAYAK vacation rental searches, the most popular destination is Chicago (83% of total searches to Illinois). The next most popular destinations are Rockford (9%) and Saint Charles (4%). Searches for vacation rentals in Champaign (4%) are also popular.

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

    In the last 72 hours, users have found Illinois vacation rentals for tonight for as low as C$ 91. Search here for similar prices

  • What types of vacation rentals are available in Illinois?

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

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

    There are a number of dog and pet-friendly Illinois vacation 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 vacation home.

Everything you need to know for your stay in Illinois

Complete your trip to Illinois

Car rentals in Illinois
Vacations in Illinois