Orangeville Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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

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Orangeville Flight & Hotel Packages

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

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was S$727, price is now S$539 per person
S$539
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,134 reviews)
O

Reviewed on 1 Jul, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,019, price is now S$695 per person
S$695
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Was excited to again stay with Omni but this property wasn’t up to the same standards as others we’ve stayed at… It was clean but just seemed “sad”

Reviewed on 1 Jul, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,006, price is now S$696 per person
S$696
per person
24 Sept - 26 Sept
found 16 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on 26 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,351, price is now S$982 per person
S$982
per person
22 Sept - 24 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was S$956, price is now S$717 per person
S$717
per person
24 Sept - 26 Sept
found 16 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,222 reviews)
Great experience! Thanks!

Reviewed on 29 Jun, 2026

Top hotels in Orangeville

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 S$173 per night from 2 Aug to 3 Aug
S$173
2 Aug - 3 Aug
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 28 Jun, 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 S$119 per night from 2 Aug to 3 Aug
S$119
2 Aug - 3 Aug
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 27 Jun, 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 S$164 per night from 19 Jul to 20 Jul
S$164
19 Jul - 20 Jul
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 26 Jun, 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 holiday package cost?
You'll find cheap prices from S$539 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.