Cheap Flights to Dufferin County from $46 (2026/2027)

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Orangeville

Flights
Orangeville

How Much Does it Cost To Fly To Dufferin County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Dec 16 - Thu, Jan 7
FLL
Fort Lauderdale - Hollywood Intl.
YYZ
Pearson Intl.
$146 Roundtrip, found 3 hours ago
$146
Roundtrip
found 3 hours ago
Select Flair Airlines flight, departing Wed, Dec 16 from Fort Lauderdale - Hollywood Intl. to Pearson Intl., returning Thu, Jan 7, priced at $146 found 3 hours ago
Wed, Nov 4 - Sat, Nov 7
DCA
Ronald Reagan Washington National
YYZ
Pearson Intl.
$234 Roundtrip, found 16 hours ago
$234
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Nov 4 from Ronald Reagan Washington National to Pearson Intl., returning Sat, Nov 7, priced at $234 found 16 hours ago
Wed, Nov 4 - Sat, Nov 7
IAD
Washington Dulles Intl.
YYZ
Pearson Intl.
$236 Roundtrip, found 16 hours ago
$236
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Nov 4 from Washington Dulles Intl. to Pearson Intl., returning Sat, Nov 7, priced at $236 found 16 hours ago
Tue, Oct 27 - Wed, Oct 28
BOS
Logan Intl.
YYZ
Pearson Intl.
$264 Roundtrip, just found
$264
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Oct 27 from Logan Intl. to Pearson Intl., returning Wed, Oct 28, priced at $264 just found
Sat, Dec 12 - Mon, Dec 14
IAD
Washington Dulles Intl.
YKF
Region of Waterloo Intl.
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Dec 12 from Washington Dulles Intl. to Region of Waterloo Intl., returning Mon, Dec 14, priced at $265 found 1 day ago
Tue, Nov 3 - Mon, Nov 9
DCA
Ronald Reagan Washington National
YKF
Region of Waterloo Intl.
$265 Roundtrip, found 2 days ago
$265
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Nov 3 from Ronald Reagan Washington National to Region of Waterloo Intl., returning Mon, Nov 9, priced at $265 found 2 days ago
Sat, Oct 31 - Wed, Nov 4
LGA
LaGuardia
YYZ
Pearson Intl.
$267 Roundtrip, just found
$267
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 31 from LaGuardia to Pearson Intl., returning Wed, Nov 4, priced at $267 just found
Fri, Nov 6 - Sun, Nov 8
EWR
Newark Liberty Intl. Airport
YYZ
Pearson Intl.
$285 Roundtrip, just found
$285
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Nov 6 from Newark Liberty Intl. Airport to Pearson Intl., returning Sun, Nov 8, priced at $285 just found
OriginDestinationTravel DatesFlights From*
YXXTorontoNovember 24 to November 27$173
YVRKitchenerOctober 28 to November 4$326
LAXTorontoOctober 28 to November 2$506
LAXKitchenerOctober 27 to October 31$588
HKGTorontoOctober 27 to November 22$861
CANTorontoNovember 26 to January 24$925
PVGTorontoNovember 18 to March 17$955
PEKTorontoNovember 12 to April 7$992
SZXTorontoDecember 23 to January 24$1,049
FOCTorontoNovember 26 to December 1$1,103
TFUTorontoNovember 7 to November 15$1,106
XIYTorontoNovember 8 to November 15$1,263
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YXXTorontoOctober 11 to October 19$335
YVRKitchenerOctober 9 to October 19$706
LAXKitchenerOctober 9 to October 11$941
LAXTorontoOctober 10 to October 16$1,069
PVGTorontoOctober 11 to November 8$1,188
PEKTorontoOctober 11 to October 31$1,264
CANTorontoOctober 11 to October 26$1,331
FOCTorontoOctober 11 to October 18$1,382
TFUTorontoOctober 9 to October 13$2,014
*Prices include taxes and fees

Best Dufferin County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Toronto
5.0-star property

Four Seasons Hotel Toronto

Dec 10 - Dec 13

3 night stay

Chicago (ORD) to Toronto (YYZ)

American Airlines • Coach

Toronto (YYZ) to Chicago (ORD)

Delta • Coach
Price was $1,713, price is now $1,165 per person
$1,165
per person
found 7 hours ago
1 Hotel Toronto
5.0-star property

1 Hotel Toronto

Dec 10 - Dec 17

7 night stay

Dallas (DFW) to Toronto (YYZ)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,420, price is now $2,291 per person
$2,291
per person
found 24 hours ago
Modern Downtown Apartments
4.0-star property

Modern Downtown Apartments

Dec 29 - Jan 2

4 night stay

Orlando (MCO) to Toronto (YYZ)

Air Canada • Coach

Toronto (YYZ) to Orlando (MCO)

Flair Airlines • Coach
Save 100% on your flight
Price was $1,973, price is now $1,417 per person
$1,417
per person
found 19 hours ago
Don't see what you're looking for?
See all available trips from Chicago to Dufferin County
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Travelers ❤️ These Dufferin County 🏨

Hockley Valley Resort

Hockley Valley Resort

3.5 out of 5
793522 3rd Line EHS Mono ON
Book a stay at this spa resort in Mono. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hockley Valley Resort and Hockley Valley Provincial Park are located nearby.
8.2/10 Very Good! (577 reviews)
"Hidden treasure and a lovely couples retreat."

Reviewed on Oct 6, 2026

Opens in a new windowHockley Valley Resort
Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites

2.5 out of 5
7 Buena Vista Drive Orangeville ON
Book a stay at this business-friendly hotel in Orangeville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Dragonfly Park and Island Lake Conservation Area are located nearby.
Opens in a new windowBest Western Plus Orangeville Inn & Suites
Blue Mountain Resort Village Suites

Blue Mountain Resort Village Suites

4 out of 5
156 Jozo Weider Blvd The Blue Mountains ON
Book a stay at this ski hotel in The Blue Mountains. Enjoy free WiFi, an outdoor pool, and 10 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Blue Mountain Ski Resort and Scandinave Spa Blue Mountain are located nearby.
Opens in a new windowBlue Mountain Resort Village Suites
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Blue Mountain Resort Inn

Blue Mountain Resort Inn

2.5 out of 5
110 Jozo Weider Blvd The Blue Mountains ON
Book a stay at this golf hotel in The Blue Mountains. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blue Mountain Ski Resort and Scandinave Spa Blue Mountain are located nearby.
8.8/10 Excellent! (1,848 reviews)
"Well maintained. Clean. Close to the village. Will stay again."

Reviewed on Oct 4, 2026

Opens in a new windowBlue Mountain Resort Inn
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 is the cheapest flight to Dufferin County?
To give you a figure to work with, the cheapest roundtrip flight to Dufferin County cost $146 in the last seven days. An easy way to score a great deal is to be flexible with your dates. This price was available on Travelocity for flights to Dufferin County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Dufferin County?
December is the cheapest month to fly to Dufferin County based on Travelocity's direct return flight demand between January and December last year. We're here to help you score a top deal so you can start preparing your escape today.
How can I check my flight status to Dufferin County?
Check for status updates on your flight to Dufferin County, make changes and plenty more from our helpful Trips portal. Found at the top right of our homepage, it's the place to view and manage your bookings. All you need to do is log in or create a new account in seconds. Savvy wanderers can also take advantage of the Travelocity app. You'll get alerts for flight delays and gate changes, as well as the ability to view and book hotels, rental cars and activities while you're out and about. If you have friends or family flying with you, it's also an useful way to share your travel itinerary with each other.
How do I find the best deals on flights to Dufferin County?
Be flexible with your travel dates and there's a strong chance you'll find an epic deal. After you've searched for flights on Travelocity, hit the "Flexible dates" box above your results to compare prices with nearby days. Also try to book ahead of time and avoid peak periods. In the last seven days, the lowest price for a return flight to Dufferin County was $146. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Dufferin County with Travelocity?
From cheap family flights to vacation packages, Travelocity has got you covered for awesome adventures. With everything at hand, you can spend more time gearing up for the fun things that await you in Dufferin County and less time on the nitty-gritty of travel planning. Plus with our Price Match Guarantee and online chat support, our mission is to make your next vacation the most magical one yet.
What are the most popular flight routes to Dufferin County?
If you're planning to catch a flight to Dufferin County, here are a few main routes that'll get you there:

  • Vancouver, BC (YVR-Vancouver Intl.) to Pearson Intl. Airport (YYZ) - 3,700 flights a month.
  • Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Pearson Intl. Airport (YYZ) - 3,622 flights a month.
  • Calgary, AB (YYC-Calgary Intl.) to Pearson Intl. Airport (YYZ) - 3,583 flights a month.

How much is a flight to Dufferin County on average?
Get your next break off to a great start by snapping up a fabulous deal with Travelocity. In the last seven days, roundtrip flights to Dufferin County cost between $146 and $2,014. Look through our site and lock in an airfare that fits in your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Dufferin County?
To get an idea of the average time of a direct flight to Dufferin County, have a look at these common routes:

  • Vancouver, BC (YVR-Vancouver Intl.) to Pearson Intl. Airport (YYZ) - 4 hours and 29 minutes
  • Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Pearson Intl. Airport (YYZ) - 1 hour and 44 minutes
  • Calgary, AB (YYC-Calgary Intl.) to Pearson Intl. Airport (YYZ) - 3 hours and 39 minutes

What can I expect on a flight to Dufferin County?
How long your flight takes and whether you go with a budget or full-service carrier will determine what to expect on board. If you're seeking long-haul flights to Dufferin County, entertainment and food should be included. After cheap flights for family vacations? Look into the deals from low-cost carriers. Typically, these airlines don't have as many inclusions, so be prepared to pay for your drinks and meals.