Orangeville Vacations from ￥662,926

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Orangeville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥1,007,204, price is now ￥662,926 per person
￥662,926
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,256 reviews)
The Silversmith Hotel in Chicago offers a fantastic stay with its prime downtown location, just steps from Millennium Park and the Art Institute. The rooms are a blend of modern comfort and historic charm, featuring high ceilings, large windows, and plush beds for a restful night. Guests consistently praise the friendly, attentive staff who provide excellent service, including helpful recommendations for local attractions and dining. While there’s no on-site restaurant, a delightful bar and breakfast is available in the lobby, and numerous dining options are within walking distance. Overall, the Silversmith Hotel provides great value and a memorable experience for both business and leisure travelers.

Reviewed on Jul 2, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥1,032,808, price is now ￥670,259 per person
￥670,259
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The staff was very friendly and the location was great!

Reviewed on Jul 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥1,111,172, price is now ￥727,868 per person
￥727,868
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on Jul 1, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥1,058,930, price is now ￥697,630 per person
￥697,630
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
An amazing hotel with an amazing river view! I will definitely be staying there again!

Reviewed on Jul 1, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥1,026,532, price is now ￥677,551 per person
￥677,551
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,141 reviews)
The location of the Arlo Chicago is super convenient and the hotel is quiet and comfy.

Reviewed on Jul 2, 2026

Find the Best Orangeville Vacation Packages

Orangeville Hotel Deals

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
The price is ￥20,560 per night from Jul 6 to Jul 7
￥20,560
￥22,817 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (909 reviews)
"The room was amazing and clean. The staff was great and very accommodating. Breakfast was good and a great start to our day. Thet have a swimming pool and jacuzzi and it was very clean. We plan to come back again."

Reviewed on Jun 28, 2026

Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
The price is ￥14,855 per night from Jul 6 to Jul 7
￥14,855
￥16,486 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (679 reviews)
"The location is great and parking is easy. Lobby was clean and front desk staff very friendly. There was a roped off area in front of the main entrance door and the elevator was broken. The room has been updated, but isn't the cleanest. The main hall carpet is really run down. Our toilet srst was ..."

Reviewed on Jun 27, 2026

Country Inn & Suites by Radisson, Stockton, IL
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is ￥19,290 per night from Jul 12 to Jul 13
￥19,290
￥21,408 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (479 reviews)
"Breakfast was good, beds were comfortable, however the carpet in the room was dirty. Parking was so-so, especially at night with the neighborhood establishments close by (ie. Liquor store). The lot on the side fills up fast and can't bring the cart across the street against 2 lanes of traffic. Staff ..."

Reviewed on Jun 26, 2026

Hampton Inn Freeport
See all 40 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.

Frequently asked questions

How much does an Orangeville vacation package cost?
You'll find cheap prices from ￥662,926 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?
January, February and November are great times to look for cheap Orangeville vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Orangeville?
Typically, a handful of days is enough to visit the top attractions during your Orangeville vacation. However, if you prefer to have more time to chill out or go on day trips, think about extending your itinerary.
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.
How to plan a trip to Orangeville?

  1. Pick your dates: The things you want to do in Orangeville and your preferred season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Orangeville.
  3. Decide your trip length: Think about how much time you want to spend discovering Orangeville. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Orangeville vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.