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Headingley

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Headingley Flights as Low as $146

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

Flair Airlines
Thu, May 7 - Mon, May 11
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$146 Roundtrip, found 2 hours ago
$146
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 $146 found 2 hours ago
Air Canada
Thu, May 14 - Tue, May 19
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$169 Roundtrip, found 5 hours ago
$169
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Thu, May 14 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 19, priced at $169 found 5 hours ago
WestJet
Fri, May 8 - Sun, May 10
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$209 Roundtrip, found 13 hours ago
$209
Roundtrip
found 13 hours ago
Select WestJet flight, departing Fri, May 8 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, May 10, priced at $209 found 13 hours ago
Porter Airlines
Fri, May 15 - Wed, May 20
YHM
John C. Munro Hamilton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$245 Roundtrip, found 3 hours ago
$245
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Fri, May 15 from John C. Munro Hamilton Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, May 20, priced at $245 found 3 hours ago
WestJet
Sun, Apr 19 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$284 Roundtrip, found 1 day ago
$284
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Apr 19 from Hartsfield-Jackson Atlanta Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Apr 25, priced at $284 found 1 day ago
Delta
Fri, May 8 - Sat, May 23
IND
Indianapolis Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 8 from Indianapolis Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, May 23, priced at $337 found 1 day ago
WestJet
Tue, May 12 - Sat, May 16
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$355 Roundtrip, found 5 hours ago
$355
Roundtrip
found 5 hours ago
Select WestJet flight, departing Tue, May 12 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, May 16, priced at $355 found 5 hours ago
Delta
Wed, Sep 2 - Mon, Sep 14
DFW
Dallas-Fort Worth Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$366 Roundtrip, found 3 hours ago
$366
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Sep 2 from Dallas-Fort Worth Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 14, priced at $366 found 3 hours ago
Delta
Sat, Aug 22 - Sat, Aug 29
IAH
George Bush Intercontinental
YWG
Winnipeg James Armstrong Richardson Intl.
$370 Roundtrip, found 4 hours ago
$370
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Aug 22 from George Bush Intercontinental to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 29, priced at $370 found 4 hours ago
WestJet
Mon, Jun 22 - Tue, Jun 30
SFO
San Francisco Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Jun 22 from San Francisco Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 30, priced at $406 found 1 day ago
Air Canada
Mon, Aug 17 - Sat, Aug 22
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$427 Roundtrip, found 22 hours ago
$427
Roundtrip
found 22 hours ago
Select Air Canada flight, departing Mon, Aug 17 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 22, priced at $427 found 22 hours ago
Delta
Wed, Sep 2 - Mon, Sep 14
DAL
Love Field
YWG
Winnipeg James Armstrong Richardson Intl.
$483 Roundtrip, found 1 day ago
$483
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 2 from Love Field to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 14, priced at $483 found 1 day ago
WestJet
Wed, Jul 29 - Wed, Aug 12
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$488 Roundtrip, found 3 hours ago
$488
Roundtrip
found 3 hours ago
Select WestJet flight, departing Wed, Jul 29 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 12, priced at $488 found 3 hours ago
Delta
Sat, Aug 1 - Tue, Aug 11
MKE
General Mitchell Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$539 Roundtrip, found 7 hours ago
$539
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Aug 1 from General Mitchell Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 11, priced at $539 found 7 hours ago
Delta
Sat, Nov 21 - Sat, Nov 28
IAD
Washington Dulles Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$594 Roundtrip, found 8 hours ago
$594
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 21 from Washington Dulles Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Nov 28, priced at $594 found 8 hours ago
Alaska Airlines
Sat, May 2 - Tue, May 5
FCA
Glacier Park Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$632 Roundtrip, found 2 days ago
$632
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, May 2 from Glacier Park Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 5, priced at $632 found 2 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 May, 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 $146, 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 $146 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$145

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! (1,415 reviews)
Excellent and quiet

Reviewed on Apr 6, 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 ...
9/10 Wonderful! (1,003 reviews)
Very clean and spacious room. Totally recommend.

Reviewed on Apr 5, 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! (2,928 reviews)
Didnt do laundry, so wouldn't know. Other then that, i enjoyed the stay.

Reviewed on Apr 5, 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! (1,391 reviews)
Was not used

Reviewed on Apr 5, 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! (2,653 reviews)
No breakfast

Reviewed on Apr 4, 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! (1,100 reviews)
The Fort Garry is a lovely old hotel. It’s fun just walking through the lobby. The Oval Room is a lovely place to have a nightcap. Our room was pleasant and very clean. The bed was comfortable. We’ll be back.

Reviewed on Apr 5, 2026

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

Alt Hotel Winnipeg

3 out of 5
310 Donald Street Winnipeg MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,223 reviews)
Great place to stay for downtown activities

Reviewed on Apr 5, 2026

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Alt Hotel Winnipeg
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! (1,209 reviews)
Our room was perfect for a family of 5.

Reviewed on Apr 3, 2026

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Birchwood Inn, BW Premier Collection
See all 617 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.