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Headingley

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Headingley Flights as Low as $132

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

Flair Airlines
Tue, Oct 6 - Sat, Oct 24
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Flair Airlines flight, departing Tue, Oct 6 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 24, priced at $132 just found
Flair Airlines
Tue, Oct 6 - Fri, Oct 23
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$140 Roundtrip, found 14 hours ago
$140
Roundtrip
found 14 hours ago
Select Flair Airlines flight, departing Tue, Oct 6 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Oct 23, priced at $140 found 14 hours ago
Porter Airlines
Tue, Oct 6 - Sat, Oct 24
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Oct 6 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 24, priced at $146 just found
Flair Airlines
Tue, Oct 6 - Sat, Oct 24
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Flair Airlines flight, departing Tue, Oct 6 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 24, priced at $147 just found
WestJet
Thu, Oct 8 - Sat, Oct 24
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$166 Roundtrip, just found
$166
Roundtrip
just found
Select WestJet flight, departing Thu, Oct 8 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 24, priced at $166 just found
Porter Airlines
Thu, Oct 8 - Wed, Oct 21
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$166 Roundtrip, just found
$166
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Oct 8 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Oct 21, priced at $166 just found
Air Canada
Wed, Sep 9 - Sat, Sep 12
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Sep 9 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Sep 12, priced at $167 found 1 day ago
Air Canada
Tue, Sep 29 - Sat, Oct 17
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$194 Roundtrip, found 3 days ago
$194
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, Sep 29 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 17, priced at $194 found 3 days ago
Air Transat
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$199 Roundtrip, found 16 hours ago
$199
Roundtrip
found 16 hours ago
Select Air Transat flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $199 found 16 hours ago
WestJet
Tue, Sep 29 - Sat, Oct 17
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$249 Roundtrip, found 14 hours ago
$249
Roundtrip
found 14 hours ago
Select WestJet flight, departing Tue, Sep 29 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 17, priced at $249 found 14 hours ago
Delta
Fri, Feb 12 - Sat, Feb 20
DTW
Detroit Metropolitan Wayne County
YWG
Winnipeg James Armstrong Richardson Intl.
$493 Roundtrip, found 14 hours ago
$493
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Feb 12 from Detroit Metropolitan Wayne County to Winnipeg James Armstrong Richardson Intl., returning Sat, Feb 20, priced at $493 found 14 hours ago
Delta
Fri, Feb 12 - Sat, Feb 20
DTW
Detroit Metropolitan Wayne County
YWG
Winnipeg James Armstrong Richardson Intl.
$550 Roundtrip, found 14 hours ago
$550
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Feb 12 from Detroit Metropolitan Wayne County to Winnipeg James Armstrong Richardson Intl., returning Sat, Feb 20, priced at $550 found 14 hours ago
Delta
Mon, Feb 8 - Tue, Feb 9
EWR
Newark Liberty Intl. Airport
YWG
Winnipeg James Armstrong Richardson Intl.
$653 Roundtrip, found 1 day ago
$653
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Feb 8 from Newark Liberty Intl. Airport to Winnipeg James Armstrong Richardson Intl., returning Tue, Feb 9, priced at $653 found 1 day ago
United
Mon, Feb 8 - Tue, Feb 9
EWR
Newark Liberty Intl. Airport
YWG
Winnipeg James Armstrong Richardson Intl.
$697 Roundtrip, found 1 day ago
$697
Roundtrip
found 1 day ago
Select United flight, departing Mon, Feb 8 from Newark Liberty Intl. Airport to Winnipeg James Armstrong Richardson Intl., returning Tue, Feb 9, priced at $697 found 1 day ago
Delta
Mon, Sep 21 - Wed, Sep 23
GRR
Gerald R. Ford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$704 Roundtrip, found 21 hours ago
$704
Roundtrip
found 21 hours ago
Select Delta flight, departing Mon, Sep 21 from Gerald R. Ford Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 23, priced at $704 found 21 hours ago
American Airlines
Fri, Feb 12 - Sat, Feb 20
DTW
Detroit Metropolitan Wayne County
YWG
Winnipeg James Armstrong Richardson Intl.
$925 Roundtrip, found 14 hours ago
$925
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Fri, Feb 12 from Detroit Metropolitan Wayne County to Winnipeg James Armstrong Richardson Intl., returning Sat, Feb 20, priced at $925 found 14 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 October, 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 $132, 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 $132 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$132

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 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! (1,015 reviews)
"The breakfast , clean rooms,"

Reviewed on Aug 12, 2026

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 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! (1,613 reviews)
"Mostly everything"

Reviewed on Aug 11, 2026

Get rates
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 ...
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Victoria Inn Hotel and Convention Centre Winnipeg
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! (1,281 reviews)
"The hotel was central and very convenient. The hotel staff were accommodating, polite and prompt. Room service breakfast was great"

Reviewed on Aug 12, 2026

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

Radisson Hotel Winnipeg Downtown

3.5 out of 5
288 Portage Ave Winnipeg MB
Stay at this hotel in Winnipeg. Enjoy free WiFi, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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Radisson Hotel Winnipeg Downtown
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
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 ...
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Birchwood Inn, BW Premier Collection
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. ...
9.2/10 Wonderful! (1,002 reviews)
"Room was spacious and clean. Fridge came pre-stocked but didn't use any of it. Quiet area and the room was quiet. Parking can be tricky since it's inside the forks, which is a busy area, but it was managable. There is a significant amount of things to do in the area."

Reviewed on Aug 12, 2026

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Inn At The Forks
See all 684 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.