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Headingley

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Headingley Flights as Low as $96

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

Flair Airlines
Thu, Sep 4 - Thu, Sep 18
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$96 Roundtrip, found 20 hours ago
$96
Roundtrip
found 20 hours ago
Select Flair Airlines flight, departing Thu, Sep 4 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Sep 18, priced at $96 found 20 hours ago
WestJet
Thu, Sep 4 - Mon, Sep 15
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select WestJet flight, departing Thu, Sep 4 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 15, priced at $103 found 3 days ago
Flair Airlines
Wed, Aug 27 - Sat, Aug 30
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Wed, Aug 27 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 30, priced at $154 found 2 days ago
Flair Airlines
Fri, Sep 5 - Mon, Sep 8
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Fri, Sep 5 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 8, priced at $162 found 2 days ago
Air Canada
Wed, Aug 6 - Wed, Aug 13
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$191 Roundtrip, found 9 hours ago
$191
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Wed, Aug 6 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 13, priced at $191 found 9 hours ago
WestJet
Sat, Sep 6 - Wed, Oct 1
YYJ
Victoria Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Sep 6 from Victoria Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Oct 1, priced at $201 found 1 day ago
United
Mon, Jul 21 - Tue, Jul 22
LAX
Los Angeles Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jul 21 from Los Angeles Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jul 22, priced at $202 found 1 day ago
United
Mon, Aug 25 - Tue, Aug 26
SFO
San Francisco Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$281 Roundtrip, found 2 days ago
$281
Roundtrip
found 2 days ago
Select United flight, departing Mon, Aug 25 from San Francisco Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 26, priced at $281 found 2 days ago
WestJet
Wed, Aug 6 - Wed, Aug 13
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$301 Roundtrip, found 19 hours ago
$301
Roundtrip
found 19 hours ago
Select WestJet flight, departing Wed, Aug 6 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 13, priced at $301 found 19 hours ago
WestJet
Tue, Sep 2 - Sun, Sep 7
DEN
Denver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago
Select WestJet flight, departing Tue, Sep 2 from Denver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 7, priced at $307 found 4 days ago
WestJet
Thu, Aug 7 - Fri, Aug 8
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$340 Roundtrip, found 4 days ago
$340
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Aug 7 from Macdonald-Cartier Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Aug 8, priced at $340 found 4 days ago
Air Canada
Tue, Oct 21 - Wed, Oct 22
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$357 Roundtrip, found 2 days ago
$357
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Oct 21 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Oct 22, priced at $357 found 2 days ago
WestJet
Sat, Jul 19 - Wed, Jul 23
IAH
George Bush Intercontinental
YWG
Winnipeg James Armstrong Richardson Intl.
$394 Roundtrip, found 1 day ago
$394
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Jul 19 from George Bush Intercontinental to Winnipeg James Armstrong Richardson Intl., returning Wed, Jul 23, priced at $394 found 1 day ago
Delta
Wed, Jul 30 - Tue, Aug 5
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$413 Roundtrip, found 20 hours ago
$413
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jul 30 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 5, priced at $413 found 20 hours ago
United
Wed, Oct 1 - Sat, Oct 4
DCA
Ronald Reagan Washington National
YWG
Winnipeg James Armstrong Richardson Intl.
$426 Roundtrip, found 19 hours ago
$426
Roundtrip
found 19 hours ago
Select United flight, departing Wed, Oct 1 from Ronald Reagan Washington National to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 4, priced at $426 found 19 hours ago
United
Wed, Jul 30 - Sat, Aug 2
SLC
Salt Lake City Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$436 Roundtrip, found 20 hours ago
$436
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jul 30 from Salt Lake City Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 2, priced at $436 found 20 hours 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 September, 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 $96, 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 $96 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$95

Last Minute Hotel Deals in Headingley

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! (1,007 reviews)
"We really like out handicap room this stay. Nicest one of all our previous stays. Only thing is a safety bar added to the shower in the middle would be beneficial."

Reviewed on Jul 1, 2025

Get rates
Best Western Plus Winnipeg West
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! (1,113 reviews)
"Overall it was a good property."

Reviewed on Jul 1, 2025

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Motel 6 Headingley, MB - 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! (2,087 reviews)
Fun place
"My only complaint is I ask for adjoining rooms but never get them! We were on two different floors, which is not really convent!"

Reviewed on Jul 2, 2025

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Victoria Inn Hotel and Convention Centre Winnipeg
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! (2,177 reviews)
"Great location to the airport"

Reviewed on Jul 3, 2025

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Lakeview Signature, Trademark Collection by Wyndham
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)
"Old world charm with modern upgrades in the heart of the city. Towels and bed linens are top notch. Fantastic staff."

Reviewed on Jul 2, 2025

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The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
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! (1,242 reviews)
"Close to downtown activities. Walking dist"

Reviewed on Jul 3, 2025

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Humphry Inn & Suites
Alt Hotel Winnipeg
Alt Hotel Winnipeg
3 out of 5
310 Donald Street, Winnipeg, MB
Stay at this 3-star eco-certified hotel in Winnipeg. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,023 reviews)
"The location of this property is terrific. It is right in the middle of everything. We could either walk 15 minutes to where we wanted to go, or take an Uber 15 minutes for the few things that were farther away. The staff was helpful and gracious. I was surprised there was no maid service, but since ..."

Reviewed on Jul 1, 2025

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Alt Hotel Winnipeg
The Grand Winnipeg Airport Hotel by Lakeview
The Grand Winnipeg Airport Hotel by Lakeview
4 out of 5
1979 Wellington Ave., Winnipeg, MB
Stay at this 4-star eco-certified hotel in Winnipeg. Enjoy free WiFi, room service, and a fitness center. Our guests praise the restaurant and the helpful staff ...
9/10 Wonderful! (1,038 reviews)
"Check in was easy and room was quiet Coffee available in the lobby early morning"

Reviewed on Jul 3, 2025

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The Grand Winnipeg Airport Hotel by Lakeview
See all 519 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.