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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.

WestJet
Wed, Jun 10 - Sun, Jun 14
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, Jun 10 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Jun 14, priced at $167 found 2 days ago
Flair Airlines
Sat, Jun 6 - Sat, Jun 20
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$176 Roundtrip, found 12 hours ago
$176
Roundtrip
found 12 hours ago
Select Flair Airlines flight, departing Sat, Jun 6 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jun 20, priced at $176 found 12 hours ago
Flair Airlines
Thu, May 7 - Mon, May 11
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$185 Roundtrip, found 2 hours ago
$185
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Thu, May 7 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 11, priced at $185 found 2 hours ago
WestJet
Sun, May 24 - Tue, May 26
YXU
London Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, May 24 from London Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 26, priced at $201 found 1 day ago
Air Canada
Thu, Jul 9 - Mon, Jul 13
YKF
Region of Waterloo Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$246 Roundtrip, found 8 hours ago
$246
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Thu, Jul 9 from Region of Waterloo Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jul 13, priced at $246 found 8 hours ago
Air Canada
Sat, May 23 - Thu, May 28
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$289 Roundtrip, found 11 hours ago
$289
Roundtrip
found 11 hours ago
Select Air Canada flight, departing Sat, May 23 from Macdonald-Cartier Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, May 28, priced at $289 found 11 hours ago
WestJet
Wed, Aug 19 - Wed, Aug 26
IAH
George Bush Intercontinental
YWG
Winnipeg James Armstrong Richardson Intl.
$364 Roundtrip, found 22 hours ago
$364
Roundtrip
found 22 hours ago
Select WestJet flight, departing Wed, Aug 19 from George Bush Intercontinental to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 26, priced at $364 found 22 hours ago
WestJet
Sun, Sep 27 - Sun, Oct 11
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$384 Roundtrip, found 13 hours ago
$384
Roundtrip
found 13 hours ago
Select WestJet flight, departing Sun, Sep 27 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Oct 11, priced at $384 found 13 hours ago
Delta
Sat, May 30 - Tue, Jun 9
DFW
Dallas-Fort Worth Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$401 Roundtrip, found 1 day ago
$401
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 30 from Dallas-Fort Worth Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 9, priced at $401 found 1 day ago
Delta
Sat, May 9 - Mon, May 11
JFK
John F. Kennedy Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$416 Roundtrip, found 15 hours ago
$416
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, May 9 from John F. Kennedy Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 11, priced at $416 found 15 hours ago
WestJet
Tue, May 12 - Sun, May 17
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$433 Roundtrip, found 6 days ago
$433
Roundtrip
found 6 days ago
Select WestJet flight, departing Tue, May 12 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, May 17, priced at $433 found 6 days ago
WestJet
Thu, Apr 30 - Tue, May 5
YQR
Regina Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$483 Roundtrip, found 4 days ago
$483
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Apr 30 from Regina Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 5, priced at $483 found 4 days ago
WestJet
Thu, Jul 2 - Mon, Jul 6
YKA
Kamloops
YWG
Winnipeg James Armstrong Richardson Intl.
$485 Roundtrip, found 4 days ago
$485
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Jul 2 from Kamloops to Winnipeg James Armstrong Richardson Intl., returning Mon, Jul 6, priced at $485 found 4 days ago
Air Canada
Sat, Jul 18 - Sat, Jul 25
YDF
Deer Lake Regional
YWG
Winnipeg James Armstrong Richardson Intl.
$600 Roundtrip, found 1 day ago
$600
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Jul 18 from Deer Lake Regional to Winnipeg James Armstrong Richardson Intl., returning Sat, Jul 25, priced at $600 found 1 day ago
United
Sat, May 16 - Mon, May 18
LAX
Los Angeles Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$601 Roundtrip, found 3 days ago
$601
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 16 from Los Angeles Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 18, priced at $601 found 3 days ago
WestJet
Sat, May 30 - Tue, Jun 9
DAL
Love Field
YWG
Winnipeg James Armstrong Richardson Intl.
$608 Roundtrip, found 4 days ago
$608
Roundtrip
found 4 days ago
Select WestJet flight, departing Sat, May 30 from Love Field to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 9, priced at $608 found 4 days 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 June, 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 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. ...
9.2/10 Wonderful! (1,450 reviews)
It was perfectly priced for a quick overnight stay. Rooms were clean, mostly quiet, and the beds were very comfortable. Great morning coffee and light breakfast was good.

Reviewed on Apr 24, 2026

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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 business-friendly hotel in Headingley. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the pool and the helpful ...
9/10 Wonderful! (1,002 reviews)
The hotel was clean, the rooms need more convenient options to plug devices in. Our stay was great, except for the part where we were woken up in the middle of the night from people yelling and fighting. Other than that, the hotel was decent.

Reviewed on Apr 24, 2026

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Best Western Plus Winnipeg West
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! (2,985 reviews)
We love staying here. No issues.

Reviewed on Apr 25, 2026

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Victoria Inn Hotel and Convention Centre Winnipeg
The Grand Winnipeg Airport Hotel by Lakeview

The Grand Winnipeg Airport Hotel by Lakeview

4 out of 5
1979 Wellington Ave. Winnipeg MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, room service, and a fitness center. Our guests praise the restaurant and the helpful ...
9.2/10 Wonderful! (1,414 reviews)
Clean room, water bottle was nice touch.

Reviewed on Apr 26, 2026

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The Grand Winnipeg Airport Hotel by Lakeview
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 ...
9/10 Wonderful! (2,698 reviews)
Great setup, extremely helpful staff and cleaners..overall amazing experience over the weekend

Reviewed on Apr 25, 2026

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Lakeview Signature, Trademark Collection by Wyndham
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

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 ...
9.2/10 Wonderful! (1,121 reviews)
It’s an old property they provide no complementary drinking water in the room you’ve to buy for 8$ per bottle and the coffee maker is too slow .!!

Reviewed on Apr 25, 2026

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The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Inn At The Forks

Inn At The Forks

3.5 out of 5
75 Forks Market Rd Winnipeg MB
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (1,006 reviews)
Very small shower , fridge didn't work, had to pay for parking

Reviewed on Apr 25, 2026

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Inn At The Forks
Comfort Inn Winnipeg Airport

Comfort Inn Winnipeg Airport

2.5 out of 5
1770 Sargent Ave Winnipeg MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
7.4/10 Good! (1,004 reviews)
There was plenty of parking. I was on the ground floor, so I was able to park outside my room. The outside of the property was very dodgy. Cans, paper, and an empty beer box. Not what you want to see. The reception area was clean and basically welcoming. The staff were pleasant. The room was excellent, ...

Reviewed on Apr 24, 2026

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Comfort Inn Winnipeg Airport
See all 627 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.