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Headingley

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Headingley Flights as Low as $167

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

Flair Airlines
Fri, Aug 8 - Sat, Aug 16
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$167 Roundtrip, found 21 hours ago
$167
Roundtrip
found 21 hours ago
Select Flair Airlines flight, departing Fri, Aug 8 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 16, priced at $167 found 21 hours ago
Flair Airlines
Mon, Sep 15 - Wed, Sep 17
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$172 Roundtrip, found 16 hours ago
$172
Roundtrip
found 16 hours ago
Select Flair Airlines flight, departing Mon, Sep 15 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 17, priced at $172 found 16 hours ago
WestJet
Wed, Sep 17 - Wed, Sep 17
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$193 Roundtrip, found 16 hours ago
$193
Roundtrip
found 16 hours ago
Select WestJet flight, departing Wed, Sep 17 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 17, priced at $193 found 16 hours ago
Flair Airlines
Mon, Sep 15 - Wed, Sep 17
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$195 Roundtrip, found 16 hours ago
$195
Roundtrip
found 16 hours ago
Select Flair Airlines flight, departing Mon, Sep 15 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 17, priced at $195 found 16 hours ago
Porter Airlines
Wed, Jun 18 - Fri, Jun 20
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Wed, Jun 18 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Jun 20, priced at $199 found 4 days ago
Porter Airlines
Wed, Jun 18 - Wed, Jun 18
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Wed, Jun 18 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Jun 18, priced at $218 found 4 days ago
Air Canada
Wed, Jun 18 - Fri, Jun 20
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Jun 18 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Jun 20, priced at $218 found 4 days ago
Porter Airlines
Tue, Jul 8 - Wed, Jul 9
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Jul 8 from Macdonald-Cartier Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Jul 9, priced at $242 found 1 day ago
Air Transat
Wed, Jun 18 - Fri, Jun 20
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select Air Transat flight, departing Wed, Jun 18 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Jun 20, priced at $248 found 4 days ago
WestJet
Sat, Aug 2 - Tue, Sep 2
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$335 Roundtrip, found 19 hours ago
$335
Roundtrip
found 19 hours ago
Select WestJet flight, departing Sat, Aug 2 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Sep 2, priced at $335 found 19 hours ago
Delta
Fri, Jul 4 - Sat, Jul 19
JFK
John F. Kennedy Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$427 Roundtrip, found 1 day ago
$427
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from John F. Kennedy Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jul 19, priced at $427 found 1 day ago
Delta
Wed, May 21 - Tue, Jun 3
BHM
Birmingham Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$747 Roundtrip, found 1 day ago
$747
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 21 from Birmingham Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 3, priced at $747 found 1 day ago
United
Fri, Jul 4 - Sat, Jul 19
JFK
John F. Kennedy Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$781 Roundtrip, found 1 day ago
$781
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jul 4 from John F. Kennedy Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jul 19, priced at $781 found 1 day ago
ITA Airways
Wed, May 28 - Tue, Jul 1
CAI
Cairo Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$839 Roundtrip, found 1 day ago
$839
Roundtrip
found 1 day ago
Select ITA Airways flight, departing Wed, May 28 from Cairo Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jul 1, priced at $839 found 1 day ago
WestJet
Tue, May 20 - Tue, May 20
YXE
John G. Diefenbaker Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,057 Roundtrip, found 1 day ago
$1,057
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, May 20 from John G. Diefenbaker Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 20, priced at $1,057 found 1 day ago
LOT-Polish Airlines
Mon, May 26 - Tue, Jul 1
CAI
Cairo Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,139 Roundtrip, found 1 day ago
$1,139
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Mon, May 26 from Cairo Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jul 1, priced at $1,139 found 1 day ago

Cheap Flights to Headingley

Fall in love at first flight with your vacation to Headingley by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Headingley on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Headingley, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Headingley

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Headingley with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the YWG airport.

What is the cheapest month to fly to Headingley?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Headingley are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Headingley?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Headingley.

What airport is best to fly into Headingley?

When you’re planning your trip to Headingley, convenience is the name of the game. Luckily, Headingley Winnipeg James Armstrong Richardson Intl. Airport is nearby so you can deplane and get going on checking off everything on your Headingley must-do list.

How much are flights to Headingley?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Headingley on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $167, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Headingley?

The trick to saving a stack of cash on your flight to Headingley? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $167 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$166

Last Minute Hotel Deals in Headingley

Motel 6 Headingley, MB - Winnipeg West
Motel 6 Headingley, MB - Winnipeg West
2 out of 5
4400 Portage Avenue, Hwy 101 North, Headingley, MB
Stay at this motel in Headingley. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,073 reviews)
"We were on a floor with some families that were very noisy. Kids were running and yelling in the hallways. One kid was crying for over an hour."

Reviewed on May 12, 2025

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Motel 6 Headingley, MB - Winnipeg West
Best Western Plus Winnipeg West
Best Western Plus Winnipeg West
2.5 out of 5
4140 Portage Avenue, Headingley, MB
Book a stay at this eco-certified hotel in Headingley. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,002 reviews)
"Excellent hotel with awesome pool. Right next to Denny’s and hockey for all center."

Reviewed on May 2, 2025

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Best Western Plus Winnipeg West
Lakeview Signature, Trademark Collection by Wyndham
Lakeview Signature, Trademark Collection by Wyndham
3 out of 5
1999 Wellington Ave, Winnipeg, MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.8/10 Excellent! (2,095 reviews)
"Fine property by the airport, great for an early flight. Our initial room had a bad smell to it, but the staff not only got us a new room, but upgraded ours. Would recommend if having an early flight and not concerned about restaurants/nightlife."

Reviewed on May 11, 2025

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Lakeview Signature, Trademark Collection by Wyndham
Victoria Inn Hotel and Convention Centre Winnipeg
Victoria Inn Hotel and Convention Centre Winnipeg
3 out of 5
1808 Wellington Ave, Winnipeg, MB
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free water park access, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (1,998 reviews)
"It was wonderful"

Reviewed on May 12, 2025

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Victoria Inn Hotel and Convention Centre Winnipeg
Canad Inns Destination Centre Fort Garry
Canad Inns Destination Centre Fort Garry
3 out of 5
1824 Pembina Hwy, Winnipeg, MB
Book a stay at this eco-certified hotel in Winnipeg. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,014 reviews)
"."

Reviewed on May 12, 2025

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Canad Inns Destination Centre Fort Garry
The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
4 out of 5
222 Broadway, Winnipeg, MB
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9/10 Wonderful! (1,001 reviews)
"Lovely experience in an historic railway hotel. Winnipeg is a joy to move about in. Pizza in the restaurant was excellent and waitstaff was great"

Reviewed on Apr 27, 2025

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The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
Mere Hotel
Mere Hotel
3.5 out of 5
333 Waterfront Drive, Winnipeg, MB
Stay at this 3.5-star business-friendly hotel in Winnipeg. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful ...
8.8/10 Excellent! (1,016 reviews)
"Great experience at Mere!"

Reviewed on May 9, 2025

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Mere Hotel
Humphry Inn & Suites
Humphry Inn & Suites
2.5 out of 5
260 Main Street, Winnipeg, MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,192 reviews)
"Stayed 2 nights while waiting for Jets Round 1, Game 7 playoff! What a game!! The hotel is downtown, walkable for most destinations in the area. Breakfast was a bit limited as the 1st morning the food seemed to run out. The staff were very friendly and helpful in providing walking directions. Parking ..."

Reviewed on May 6, 2025

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Humphry Inn & Suites
See all 517 properties in Headingley
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.