Cheap Flights to Durham Region from $49 (2026/2027)

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Oshawa

Flights
Oshawa

How Much Does it Cost To Fly To Durham Region?

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

Thu, Sep 17 - Thu, Sep 24
FLL
Fort Lauderdale - Hollywood Intl.
YYZ
Pearson Intl.
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Pearson Intl., returning Thu, Sep 24, priced at $167 found 1 hour ago
Sat, Jun 6 - Sat, Jun 13
IAD
Washington Dulles Intl.
YTZ
Billy Bishop Toronto City
$208 Roundtrip, found 3 hours ago
$208
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Sat, Jun 6 from Washington Dulles Intl. to Billy Bishop Toronto City, returning Sat, Jun 13, priced at $208 found 3 hours ago
Fri, Jun 5 - Tue, Jun 9
ORD
O'Hare Intl.
YYZ
Pearson Intl.
$218 Roundtrip, found 1 hour ago
$218
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Jun 5 from O'Hare Intl. to Pearson Intl., returning Tue, Jun 9, priced at $218 found 1 hour ago
Tue, Jun 16 - Fri, Jun 19
ORD
O'Hare Intl.
YTZ
Billy Bishop Toronto City
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Jun 16 from O'Hare Intl. to Billy Bishop Toronto City, returning Fri, Jun 19, priced at $226 found 1 day ago
Wed, May 13 - Tue, May 19
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$226 Roundtrip, just found
$226
Roundtrip
just found
Select Porter Airlines flight, departing Wed, May 13 from Midway Intl. to Billy Bishop Toronto City, returning Tue, May 19, priced at $226 just found
Mon, Jun 8 - Fri, Jun 12
DCA
Ronald Reagan Washington National
YTZ
Billy Bishop Toronto City
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Jun 8 from Ronald Reagan Washington National to Billy Bishop Toronto City, returning Fri, Jun 12, priced at $237 found 1 day ago
Thu, May 28 - Fri, May 29
DCA
Ronald Reagan Washington National
YYZ
Pearson Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, May 28 from Ronald Reagan Washington National to Pearson Intl., returning Fri, May 29, priced at $240 found 2 days ago
Sat, Jun 6 - Mon, Jun 8
MDW
Midway Intl.
YYZ
Pearson Intl.
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 6 from Midway Intl. to Pearson Intl., returning Mon, Jun 8, priced at $243 found 3 days ago
Sat, Aug 15 - Sun, Aug 16
BOS
Logan Intl.
YTZ
Billy Bishop Toronto City
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Aug 15 from Logan Intl. to Billy Bishop Toronto City, returning Sun, Aug 16, priced at $244 found 1 day ago
OriginDestinationTravel DatesFlights From*
YXXTorontoMay 31 to June 4$248
YVRTorontoJune 11 to June 14$304
LAXTorontoJuly 13 to July 14$339
LAXTorontoJune 10 to June 15$437
PVGTorontoMay 25 to June 1$1,159
HKGTorontoMay 11 to November 4$1,244
CANTorontoJuly 8 to July 29$1,253
XIYTorontoMay 7 to May 12$1,316
PEKTorontoMay 7 to May 11$1,325
FOCTorontoJune 12 to July 19$1,443
CTUTorontoMay 26 to September 16$1,457
SZXTorontoJuly 7 to August 3$1,755
HKGTorontoMay 7 to May 26$1,906
PEKTorontoMay 7 to May 11$4,405
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YVRTorontoApril 25 to April 29$521
LAXTorontoApril 26 to May 6$671
LAXTorontoApril 25 to April 27$814
YVRTorontoApril 26 to April 27$878
PVGTorontoApril 26 to May 16$1,949
*Prices include taxes and fees

Best Durham Region Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Mount Alverno Luxury Resorts
2.5-star property

Mount Alverno Luxury Resorts

Jun 28 - Jul 3

5 night stay

Chicago (ORD) to Toronto (YYZ)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,034, price is now $746 per person
$746
per person
found 1 day ago
Luxury 2 bedroom 2 full baths rooms
4.0-star property

Luxury 2 bedroom 2 full baths rooms

Jul 16 - Jul 21

5 night stay

Tampa (TPA) to Toronto (YYZ)

American Airlines • Non-stop • Coach

Toronto (YYZ) to Tampa (TPA)

Delta • Non-stop • Coach
Price was $1,133, price is now $808 per person
$808
per person
found 1 day ago
The Sutton Place Hotel Toronto
4.5-star property

The Sutton Place Hotel Toronto

Jun 9 - Jun 15

6 night stay

Atlanta (ATL) to Toronto (YYZ)

Delta • Coach

Toronto (YYZ) to Atlanta (ATL)

Air Canada • Coach
Price was $2,732, price is now $1,982 per person
$1,982
per person
found 18 hours ago
Don't see what you're looking for?
See all available trips from Chicago to Durham Region
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Travelers ❤️ These Durham Region 🏨

Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave Pickering ON
Book a stay at this business-friendly hotel in Pickering. Enjoy free WiFi, free parking, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pickering Casino Resort and Cineplex Cinemas Pickering are located nearby.
9/10 Wonderful! (4,543 reviews)
Clean room, well equipped

Reviewed on Apr 22, 2026

Opens in a new windowPickering Casino Resort Hotel
Great Blue Heron Hotel

Great Blue Heron Hotel

4 out of 5
21777 Island Rd Scugog ON
Book a stay at this business-friendly hotel in Scugog. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Great Blue Heron Charity Casino and Seven Mile Island are located nearby.
9.2/10 Wonderful! (998 reviews)
Clean room, and the pillows and bedding are very comfortable, friendly staff

Reviewed on Apr 20, 2026

Opens in a new windowGreat Blue Heron Hotel
Super 8 by Wyndham Ajax/Toronto On

Super 8 by Wyndham Ajax/Toronto On

2 out of 5
210 Westney Rd S Ajax ON
Book a stay at this business-friendly hotel in Ajax. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pickering Casino Resort and Rotary Park are located nearby.
6.8/10 (1,344 reviews)
Staff were very nice & room was clean. The 3rd floor had a bit of a musty smell in the hallway & this hotel houses a lot of construction workers so there was a lot of big trucks running outside at 5 am and heavy work boots stomping around very early.

Reviewed on Apr 21, 2026

Opens in a new windowSuper 8 by Wyndham Ajax/Toronto On
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Travelodge by Wyndham Oshawa Whitby

Travelodge by Wyndham Oshawa Whitby

2 out of 5
940 Champlain Avenue Oshawa ON
Book a stay at this business-friendly hotel in Oshawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Lynde Shores Conservation Area and Landmark Cinemas Whitby are located nearby.
6.8/10 (1,028 reviews)
Swimming pool out of order and hot tub, parkikg lot rough shape potholes, the 401 kept me up all night no sleep.

Reviewed on Apr 19, 2026

Opens in a new windowTravelodge by Wyndham Oshawa Whitby
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 Durham Region?
Within the last seven days, the cheapest roundtrip flight to Durham Region cost $167 on this site. Search through our excellent deals, make a booking and get ready for your next trip. This price was available on Travelocity for flights to Durham Region departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Durham Region?
Plan your itinerary and then jet away with any of the 18 airlines that fly to Durham Region. Book a seat with the popular air carrier, Porter Airlines. It offers approximately 953 flights every month to Pickering, Durham Region's gateway city, so finding your perfect fare should be a snap.
What is the cheapest month to fly to Durham Region?
For your biggest chance at locking in a fantastic flight deal, organize your getaway during September. Based on Travelocity's direct flight demand from January to December last year, it's the most affordable time to jet off to Durham Region.
How can I check my flight status to Durham Region?
There are a few ways you can check on your flights. You'll discover all the info you need in our Trips portal, which is located at the top of our homepage. Sign in or create an account — you'll then be able to access and manage your bookings whenever you want. For those on the move, the Travelocity app can also help you look up the status of your flight to Durham Region, as well as share travel details with any members of your family flying with you.
How do I find the best deals on flights to Durham Region?
Be flexible with your travel dates and there's a good chance you'll find an amazing deal. After you've searched for flights on Travelocity, click the "Flexible dates" feature above your results to see all the prices for surrounding days. Also try to book ahead of time and avoid the high season. In the last seven days, the lowest price for a return flight to Durham Region was $167. 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 Durham Region with Travelocity?
Pack your luggage and prepare for an amazing adventure with Travelocity. We'll help you track down all the top deals on cheap flights to Durham Region. Whether you're looking for flexible airfares with plenty of wiggle room or cheap family flights on low-cost airlines, we've got what you need.
What are the most popular flight routes to Durham Region?
As a popular destination, you'll find plenty of ways to get to Durham Region. Here are some of the top routes:

  • 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 Durham Region on average?
Roundtrip flights to Durham Region were priced between $167 and $4,405 in the last seven days. When you see an airfare that best fits your budget, get in quick. Cheap deals don't stick around forever! 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 Durham Region?
Below you can see a selection of leading direct flights to Durham Region and their average journey times:

  • 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 Durham Region?
That depends on several things. Is your flight to Durham Region short, medium or long haul? Will you fly with a full-service airline or a budget option? These things will influence your travel experience. If you're traveling long haul, many airlines include food, drink and entertainment. Budget carriers are a terrific option when it comes to cheap flights for family vacations and quick trips. However, they usually won't have the same inclusions as a full-service carrier.