Orangeville Vacations from $365

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The Latest Orangeville vacation packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $597, price is now $365 per person
$365
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug 26, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $706, price is now $401 per person
$401
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Great hotel, very clean, good breakfast choices and a convenient location

Reviewed on Sep 4, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,980, price is now $1,221 per person
$1,221
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $843, price is now $588 per person
$588
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on Aug 18, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $882, price is now $620 per person
$620
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
Great place esp last minute

Reviewed on Sep 5, 2025

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Orangeville Hotel Deals

Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Sep 21 to Sep 22
$98 total
Sep 21 - Sep 22
Total with taxes and fees
Baymont by Wyndham Freeport
Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive, Freeport, IL
Fully refundable
$110 nightly
The price is $122 total per night from Sep 21 to Sep 22
$122 total
Sep 21 - Sep 22
Total with taxes and fees
Country Inn & Suites by Radisson, Freeport, IL
AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $122 total per night from Sep 21 to Sep 22
$122 total
Sep 21 - Sep 22
Total with taxes and fees
AmericInn by Wyndham Monroe
See all 37 properties in Orangeville
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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Frequently asked questions

How much does an Orangeville vacation package cost?
You'll find cheap prices from $365 on Expedia for your Orangeville getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Orangeville costs.
What are the cheapest months to go to Orangeville?
You can generally find lower prices and greater availability in December, January and February. Browse our cheap Orangeville vacation packages and you could land some excellent off-season deals.
How many days is enough for Orangeville?
With a well-organized schedule, you can easily visit the main Orangeville attractions in a few days. But if you want to discover hidden gems or go on day trips, think about booking your Orangeville vacation for longer.
How to find the best Orangeville package deals?
Landing a cheap Orangeville package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Orangeville package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Orangeville vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can customize your Orangeville getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Orangeville?
If you have your Orangeville travel dates confirmed, book early to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later Orangeville vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Orangeville trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.