Book Holiday Homes in Illinois

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Explore these top cities in Illinois

Featured Holiday Homes in Illinois

* On the Wine Trail * Hot Tub * Wi-Fi *

* On the Wine Trail * Hot Tub * Wi-Fi *

Alto Pass
A stay at this vacation home places you in the heart of Alto Pass, steps from Shawnee National Forest and 15 minutes by foot from Peachbarn Winery.
* On the Wine Trail * Hot Tub * Wi-Fi *
Notting Hill Cottage

Notting Hill Cottage

Alto Pass
With a stay at this vacation home in Alto Pass, you'll be a 1-minute drive from Shawnee National Forest and 6 minutes from Peachbarn Winery.
Notting Hill Cottage
1842 Bavarian Brew House

1842 Bavarian Brew House

Galena
With a stay at this vacation home in Galena, you'll be within a 10-minute walk of Galena-Jo Daviess County History Museum and West Street Sculpture Park.
1842 Bavarian Brew House
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Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!

Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!

Washington
With a stay at this vacation home in Washington, you'll be within a 5-minute walk of Washington Square and Sweitzer Park.
Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chicago
Located in Chicago (Humboldt Park), this vacation home is within a 10-minute drive of Michigan Avenue and Wrigley Field.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.

Galena
With a stay at this vacation home in Galena (The Galena Territory), you'll be 10 minutes by car from Eagle Ridge Resort Golf.
BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch.
Stunning / Spacious 6BD Home + garage - Bucktown!

Stunning / Spacious 6BD Home + garage - Bucktown!

Chicago
With a stay at this vacation home in Chicago (Bucktown), you'll be a 5-minute drive from Wrigley Field and 7 minutes from Michigan Avenue.
Stunning / Spacious 6BD Home + garage - Bucktown!
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing

Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing

Galena
With a stay at this vacation home in Galena (The Galena Territory), you'll be within a 15-minute drive of Eagle Ridge Resort Golf and Washburne House Historic ...
Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing
Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests

Aurora
Located in Aurora, this vacation home is within a 5-minute drive of Copley Memorial Hospital and Rush-Copley Medical Center.
Furnished Private home in Aurora sleeps 9 guests
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Illinois Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Illinois vacation homes are the perfect way for you to wing it.

Holiday houses in Illinois let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Illinois in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Illinois adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Illinois with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Illinois vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Illinois Holiday Homes essential information

Accommodation
2159 Holiday Homes
Lowest Price
AU$175
Highest Price
AU$309
Popular accommodation
* On the Wine Trail * Hot Tub * Wi-Fi *, Notting Hill Cottage, 1842 Bavarian Brew House, Newly remodeled historic house just steps from the WASHINGTON SQUARE! Sleeps 10!, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, BIG 5BR/5.5BA all ensuite baths, Hot Tub, Screen Porch. , Stunning / Spacious 6BD Home + garage - Bucktown!, Private 3BR/2BA near golf, historic Galena, lake, owner's club, hiking, skiing, Furnished Private home in Aurora sleeps 9 guests

Top trending hotels in Illinois

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 23 Dec to 24 Dec
AU$196
includes taxes & fees
23 Dec - 24 Dec
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 21 Jan to 22 Jan
AU$175
includes taxes & fees
21 Jan - 22 Jan 2025
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$309 per night from 10 Jan to 11 Jan
AU$309
includes taxes & fees
10 Jan - 11 Jan 2025
Hyatt Regency Chicago is centrally located in Chicago, a 4-minute walk from Chicago Riverwalk and 7 minutes by foot from Michigan Avenue Bridge.
Hyatt Regency Chicago
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Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$208 per night from 7 Jan to 8 Jan
AU$208
includes taxes & fees
7 Jan - 8 Jan 2025
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel is centrally located in Chicago, a 3-minute walk from Merchandise Mart and 14 minutes by foot from Chicago ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
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See all available properties in Illinois
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.