Orangeville Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Orangeville

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 22 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Been there a couple times always a nice stay, great location

Reviewed on 8 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 22 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on 7 Jul 2025

The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 22 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Didn’t receive vip perks. Which I figured they wouldn’t as that seems to happen with most side perks off the app. Rooms were nice but had to ask for additional towel as there was only one in room. Staff was very friendly. Checking went smooth. Would recommend.

Reviewed on 8 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on 7 Jul 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,097 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

Top hotels in Orangeville

AmericInn by Wyndham Monroe
AmericInn by Wyndham Monroe
2.5 out of 5
424 4th Ave, Monroe, WI
The price is €103 per night from 27 Jul to 28 Jul
€103
27 Jul - 28 Jul
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 €84 per night from 27 Jul to 28 Jul
€84
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (656 reviews)
"Ok"

Reviewed on 6 Jul 2025

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
The price is €112 per night from 20 Jul to 21 Jul
€112
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (790 reviews)
"Dining area under repair. Breakfast great"

Reviewed on 5 Jul 2025

Country Inn & Suites by Radisson, Freeport, IL
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 €857 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.