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Headingley

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Headingley Flights as Low as $109

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

Flair Airlines
Fri, May 9 - Mon, May 12
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Flair Airlines flight, departing Fri, May 9 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 12, priced at $109 found 6 days ago
WestJet
Fri, May 9 - Mon, May 12
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, May 9 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 12, priced at $158 found 6 days ago
Porter Airlines
Fri, May 30 - Sun, Jun 1
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, May 30 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Jun 1, priced at $159 found 2 days ago
Flair Airlines
Fri, May 30 - Sun, Jun 1
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Fri, May 30 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Jun 1, priced at $159 found 2 days ago
Air Transat
Fri, May 30 - Sun, Jun 1
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Air Transat flight, departing Fri, May 30 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Jun 1, priced at $174 found 2 days ago
Flair Airlines
Fri, May 9 - Mon, May 12
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Flair Airlines flight, departing Fri, May 9 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 12, priced at $176 found 6 days ago
WestJet
Fri, May 9 - Mon, May 12
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select WestJet flight, departing Fri, May 9 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, May 12, priced at $181 found 6 days ago
Flair Airlines
Sat, May 17 - Wed, May 21
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$183 Roundtrip, found 6 hours ago
$183
Roundtrip
found 6 hours ago
Select Flair Airlines flight, departing Sat, May 17 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, May 21, priced at $183 found 6 hours ago
Flair Airlines
Fri, Sep 12 - Mon, Sep 15
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Fri, Sep 12 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 15, priced at $183 found 1 day ago
Air Canada
Sat, May 17 - Wed, May 21
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Sat, May 17 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, May 21, priced at $185 found 6 hours ago
Porter Airlines
Wed, May 21 - Thu, May 22
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Wed, May 21 from Macdonald-Cartier Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, May 22, priced at $197 found 1 day ago
WestJet
Wed, May 7 - Wed, May 14
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select WestJet flight, departing Wed, May 7 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, May 14, priced at $199 found 6 days ago
Air Transat
Wed, May 21 - Thu, May 22
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Air Transat flight, departing Wed, May 21 from Macdonald-Cartier Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, May 22, priced at $228 found 1 day ago
Air Canada
Sat, May 17 - Sun, May 18
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$244 Roundtrip, found 23 hours ago
$244
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Sat, May 17 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, May 18, priced at $244 found 23 hours ago
Air Canada
Tue, May 13 - Sun, May 18
IAH
George Bush Intercontinental
YWG
Winnipeg James Armstrong Richardson Intl.
$366 Roundtrip, found 6 hours ago
$366
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Tue, May 13 from George Bush Intercontinental to Winnipeg James Armstrong Richardson Intl., returning Sun, May 18, priced at $366 found 6 hours ago
Air North
Thu, May 1 - Thu, May 1
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$996 Roundtrip, found 1 day ago
$996
Roundtrip
found 1 day ago
Select Air North flight, departing Thu, May 1 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, May 1, priced at $996 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 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 $109, 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 $109 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$109

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, Hwy 101 North, Headingley, MB
The price is $84 per night from May 5 to May 6
$84
includes taxes & fees
May 5 - May 6
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! (1,039 reviews)
"Very nice hotel. Clean!"

Reviewed on Apr 25, 2025

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
The price is $127 per night from May 13 to May 14
$127
includes taxes & fees
May 13 - May 14
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! (1,003 reviews)
Convenient Location
"Room was spacious and comfortable. Complimentary breakfast was about average. Restaurant and truck stop beside hotel for convenience."

Reviewed on Apr 23, 2025

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
The price is $130 per night from May 4 to May 5
$130
includes taxes & fees
May 4 - May 5
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! (1,978 reviews)
"Very clean, elevators oddly located. Pool was warm, kids enjoyed. Lack of parental supervision an issue in pool area. Plenty of towels for everyone."

Reviewed on Apr 27, 2025

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
The price is $126 per night from Apr 30 to May 1
$126
includes taxes & fees
Apr 30 - May 1
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! (2,071 reviews)
"Nothing"

Reviewed on Apr 28, 2025

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
The price is $99 per night from May 19 to May 20
$99
includes taxes & fees
May 19 - May 20
Book a stay at this eco-certified hotel in Winnipeg. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,009 reviews)
Good theme Suite
"Was decent time, the shower was a bit dirty on the floor and the bath tub had jets but they didn’t look like they’d be cleaned properly either. But overall the room was nice, interesting. The elevator in the hotel is very sketchy tho…makes a lot of odd noises and clunky The buffet was decent as well, ..."

Reviewed on Apr 28, 2025

Canad Inns Destination Centre Fort Garry
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
The price is $154 per night from May 18 to May 19
$154
includes taxes & fees
May 18 - May 19
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! (1,005 reviews)
"Lovely experience in an historic railway hotel. Winnipeg is a joy to move about in. Pizza in the restaurant was excellent and waitstaff was great"

Reviewed on Apr 27, 2025

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
Travelodge by Wyndham Winnipeg East
Travelodge by Wyndham Winnipeg East
2 out of 5
20 Alpine Ave, St Annes Road, Winnipeg, MB
The price is $81 per night from May 11 to May 12
$81
includes taxes & fees
May 11 - May 12
Book a stay at this eco-certified hotel in Winnipeg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8/10 Very Good! (1,431 reviews)
Winnipeg trip
"Went for medical trip. Hotel was older but very nice and clean. Rooms are big with fridges, microwave and coffee makers. Pool is big and warm. Staff was very good. Only complaint might be complementary breakfast is very basic. No bacon and eggs. But from the price you pay, especially in winnipeg ..."

Reviewed on Apr 23, 2025

Travelodge by Wyndham Winnipeg East
Hampton Inn by Hilton Winnipeg Downtown
Hampton Inn by Hilton Winnipeg Downtown
2.5 out of 5
330 York Avenue, Winnipeg, MB
The price is $145 per night from May 11 to May 12
$145
includes taxes & fees
May 11 - May 12
Book a stay at this golf hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions Canada Life Centre and Polo Park ...
9.4/10 Exceptional! (243 reviews)
"Friendly staff , cleanliness and accessible for downtown area."

Reviewed on Apr 27, 2025

Hampton Inn by Hilton Winnipeg Downtown
See all 512 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.