Orangeville Holidays

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Top Flight + Hotel Deals in Orangeville

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,199, price is now €792 per person
€792
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Everything was nice!!

Reviewed on 23 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,420, price is now €868 per person
€868
per person
2 Nov - 7 Nov
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 15 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,825, price is now €1,216 per person
€1,216
per person
10 Oct - 14 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.

Reviewed on 23 Aug 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 €74 per night from 21 Sept to 22 Sept
€74
21 Sept - 22 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug 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 €104 per night from 21 Sept to 22 Sept
€104
21 Sept - 22 Sept
includes taxes & fees
8.6/10 Excellent! (362 reviews)
"Nice place to stay. We didn't like that you rent out the pool so it was full of kids and families that were not staying at the hotel. We tried using the pool and hot tub but it was so loud with kids we left. One of the reason we stayed was so we could use the pool and hot tub. Kitchen lady was lovely!! ..."

Reviewed on 19 Aug 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 €81 per night from 21 Sept to 22 Sept
€81
21 Sept - 22 Sept
includes taxes & fees
8/10 Very Good! (679 reviews)
"Staff and service were great. Carpet and walls/trim on all floors were dirty and peeling. Overall a good stay."

Reviewed on 20 Aug 2025

Baymont by Wyndham Freeport
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.

Frequently asked questions

How much does an Orangeville holiday package cost?
You'll find cheap prices from €792 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.