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Headingley

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Headingley Flights as Low as $220

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

Flair Airlines
Thu, Nov 5 - Fri, Nov 20
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$220 Roundtrip, found 1 hour ago
$220
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Thu, Nov 5 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Nov 20, priced at $220 found 1 hour ago
Flair Airlines
Thu, Dec 17 - Fri, Dec 25
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$228 Roundtrip, found 7 hours ago
$228
Roundtrip
found 7 hours ago
Select Flair Airlines flight, departing Thu, Dec 17 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Dec 25, priced at $228 found 7 hours ago
WestJet
Tue, Dec 15 - Wed, Dec 16
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$319 Roundtrip, found 4 hours ago
$319
Roundtrip
found 4 hours ago
Select WestJet flight, departing Tue, Dec 15 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Dec 16, priced at $319 found 4 hours ago
WestJet
Wed, Nov 4 - Thu, Nov 12
ATL
Hartsfield-Jackson Atlanta Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$332 Roundtrip, found 9 hours ago
$332
Roundtrip
found 9 hours ago
Select WestJet flight, departing Wed, Nov 4 from Hartsfield-Jackson Atlanta Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Nov 12, priced at $332 found 9 hours ago
WestJet
Sat, Nov 28 - Fri, Dec 11
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$380 Roundtrip, found 1 day ago
$380
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Nov 28 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Dec 11, priced at $380 found 1 day ago
Delta
Thu, Jan 7 - Fri, Jan 8
PHX
Sky Harbor Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$449 Roundtrip, found 3 hours ago
$449
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Jan 7 from Sky Harbor Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Jan 8, priced at $449 found 3 hours ago
WestJet
Mon, Nov 2 - Wed, Nov 4
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$452 Roundtrip, found 11 hours ago
$452
Roundtrip
found 11 hours ago
Select WestJet flight, departing Mon, Nov 2 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Nov 4, priced at $452 found 11 hours ago
Air Canada
Wed, Nov 4 - Tue, Nov 17
NAS
Lynden Pindling Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$459 Roundtrip, found 4 hours ago
$459
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Wed, Nov 4 from Lynden Pindling Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Nov 17, priced at $459 found 4 hours ago
Air Canada
Fri, Nov 20 - Sat, Nov 28
BZE
Philip S. W. Goldson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$494 Roundtrip, found 11 hours ago
$494
Roundtrip
found 11 hours ago
Select Air Canada flight, departing Fri, Nov 20 from Philip S. W. Goldson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Nov 28, priced at $494 found 11 hours ago
Delta
Mon, Nov 23 - Wed, Nov 25
DCA
Ronald Reagan Washington National
YWG
Winnipeg James Armstrong Richardson Intl.
$557 Roundtrip, found 22 hours ago
$557
Roundtrip
found 22 hours ago
Select Delta flight, departing Mon, Nov 23 from Ronald Reagan Washington National to Winnipeg James Armstrong Richardson Intl., returning Wed, Nov 25, priced at $557 found 22 hours ago
WestJet
Wed, Oct 21 - Sat, Oct 24
YUL
Pierre Elliott Trudeau Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$571 Roundtrip, found 6 days ago
$571
Roundtrip
found 6 days ago
Select WestJet flight, departing Wed, Oct 21 from Pierre Elliott Trudeau Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 24, priced at $571 found 6 days ago
American Airlines
Wed, Dec 9 - Fri, Dec 11
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$611 Roundtrip, found 7 hours ago
$611
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Dec 9 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Dec 11, priced at $611 found 7 hours ago
American Airlines
Tue, Nov 3 - Mon, Nov 9
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$692 Roundtrip, found 9 hours ago
$692
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Nov 3 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Nov 9, priced at $692 found 9 hours ago
Delta
Tue, Nov 10 - Mon, Nov 23
DFW
Dallas-Fort Worth Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$730 Roundtrip, found 1 day ago
$730
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 10 from Dallas-Fort Worth Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Nov 23, priced at $730 found 1 day ago
Delta
Tue, Feb 16 - Thu, Feb 25
STL
Lambert-St. Louis Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$790 Roundtrip, found 1 day ago
$790
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 16 from Lambert-St. Louis Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Feb 25, priced at $790 found 1 day ago
Delta
Tue, Oct 27 - Sat, Oct 31
LAS
Harry Reid Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$831 Roundtrip, found 1 day ago
$831
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 27 from Harry Reid Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 31, priced at $831 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 November, 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 $220, 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 $220 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$219

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! (1,687 reviews)
"The room were clean and bright. The pool area was really nice. The only thing is no breakfast,"

Reviewed on Oct 19, 2026

Get rates
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 ...
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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! (3,297 reviews)
"Clean spacious room. Couteous staff."

Reviewed on Oct 19, 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 ...
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The Grand Winnipeg Airport Hotel by Lakeview
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. ...
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Inn At The Forks
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 ...
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Lakeview Signature, Trademark Collection by Wyndham
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 family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (1,490 reviews)
"It was good, the swimming was fun, no complaints on anything except there should be water bottles available for free or cheap"

Reviewed on Oct 18, 2026

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Canad Inns Destination Centre Fort Garry
Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

3 out of 5
2520 Portage Ave Winnipeg MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,249 reviews)
"Swimming pool and Indoor playground was great. Our room with Kitchen was fantastic it was very comfortable."

Reviewed on Oct 19, 2026

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Birchwood Inn, BW Premier Collection
See all 700 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.