Orangeville Packages (Flight + Hotel)

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Top Orangeville Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on 8 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
The TV didn't work and made a hissing sound and the tub took hours to drain after being filled. Not big deals overall, but when I mentionned it a check-out, the staff member only said sorry and did not make a note of the issues. Presumably they will get fixed when someone complains more aggressively.

Reviewed on 15 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 5 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,773 reviews)
Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret it!

Reviewed on 15 Jul 2025

Top hotels in Orangeville

Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is ฿2,662 per night from 17 Aug to 18 Aug
฿2,662
฿2,954 total
17 Aug - 18 Aug
includes taxes & fees
6.8/10 (326 reviews)
hotel clerk very nice and helpful
"the room was very nice and the hotel clerk was very nice and she was very helpful"

Reviewed on 13 Jul 2025

Super 8 by Wyndham Freeport
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
The price is ฿3,864 per night from 17 Aug to 18 Aug
฿3,864
฿4,231 total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (348 reviews)
"I liked the proximity to other businesses in the area. Loved the breakfast the next morning! Room was a little snug between the end of the bed and the dresser."

Reviewed on 4 Jul 2025

AmericInn by Wyndham Monroe
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
The price is ฿2,953 per night from 17 Aug to 18 Aug
฿2,953
฿3,277 total
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (662 reviews)
"We had a good stay with decent breakfast choices."

Reviewed on 14 Jul 2025

Baymont by Wyndham Freeport
See all 38 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 holiday package cost?
You'll find cheap prices from ฿13,514 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 holiday to Orangeville costs.
What are the cheapest months to go to Orangeville?
January, February and November are great times to look for cheap Orangeville holiday 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 holiday. 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 holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking stays and flights individually. Better still, you can customise 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 holiday 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 travelling 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 customised Orangeville holiday package.

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