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Headingley

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Headingley Flights as Low as $136

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

WestJet
Mon, Aug 25 - Wed, Sep 3
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Aug 25 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 3, priced at $136 found 1 day ago
Flair Airlines
Fri, Sep 12 - Mon, Sep 15
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select Flair Airlines flight, departing Fri, Sep 12 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Sep 15, priced at $137 found 11 hours ago
WestJet
Mon, Aug 25 - Wed, Sep 3
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Aug 25 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 3, priced at $159 found 1 day ago
Air Canada
Mon, Aug 25 - Wed, Sep 3
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Aug 25 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Sep 3, priced at $168 found 1 day ago
Porter Airlines
Fri, Nov 7 - Mon, Nov 10
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Fri, Nov 7 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Nov 10, priced at $191 found 6 days ago
WestJet
Thu, Aug 28 - Sat, Aug 30
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select WestJet flight, departing Thu, Aug 28 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 30, priced at $214 found 6 days ago
Air Transat
Fri, Nov 7 - Mon, Nov 10
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Air Transat flight, departing Fri, Nov 7 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Nov 10, priced at $217 found 6 days ago
United
Mon, Aug 25 - Tue, Aug 26
SFO
San Francisco Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$305 Roundtrip, found 5 hours ago
$305
Roundtrip
found 5 hours ago
Select United flight, departing Mon, Aug 25 from San Francisco Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 26, priced at $305 found 5 hours ago
Delta
Fri, Oct 24 - Sat, Oct 25
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$402 Roundtrip, found 22 hours ago
$402
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, Oct 24 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 25, priced at $402 found 22 hours ago
WestJet
Wed, Dec 10 - Wed, Dec 24
NAS
Lynden Pindling Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$576 Roundtrip, found 15 hours ago
$576
Roundtrip
found 15 hours ago
Select WestJet flight, departing Wed, Dec 10 from Lynden Pindling Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Dec 24, priced at $576 found 15 hours ago
Delta
Wed, Sep 10 - Fri, Sep 19
DAL
Love Field
YWG
Winnipeg James Armstrong Richardson Intl.
$578 Roundtrip, found 4 days ago
$578
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 10 from Love Field to Winnipeg James Armstrong Richardson Intl., returning Fri, Sep 19, priced at $578 found 4 days ago
United
Wed, Aug 13 - Tue, Aug 26
RNO
Reno-Tahoe Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$673 Roundtrip, found 14 hours ago
$673
Roundtrip
found 14 hours ago
Select United flight, departing Wed, Aug 13 from Reno-Tahoe Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 26, priced at $673 found 14 hours ago
WestJet
Tue, Aug 26 - Sun, Sep 7
MBJ
Sir Donald Sangster Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$676 Roundtrip, found 16 hours ago
$676
Roundtrip
found 16 hours ago
Select WestJet flight, departing Tue, Aug 26 from Sir Donald Sangster Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 7, priced at $676 found 16 hours ago
United
Thu, Aug 21 - Sat, Aug 30
SAV
Savannah - Hilton Head Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$701 Roundtrip, found 15 hours ago
$701
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Aug 21 from Savannah - Hilton Head Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Aug 30, priced at $701 found 15 hours ago
United
Sat, May 30 - Sat, Jun 20
MCI
Kansas City Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$743 Roundtrip, found 1 day ago
$743
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 30 from Kansas City Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jun 20, priced at $743 found 1 day ago
Delta
Mon, Dec 15 - Tue, Dec 30
MHH
Marsh Harbour
YWG
Winnipeg James Armstrong Richardson Intl.
$892 Roundtrip, found 15 hours ago
$892
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Dec 15 from Marsh Harbour to Winnipeg James Armstrong Richardson Intl., returning Tue, Dec 30, priced at $892 found 15 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 August, 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 $136, 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 $136 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$135

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! (1,017 reviews)
"Close to the golf course"

Reviewed on Jul 24, 2025

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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! (1,125 reviews)
"Excellent pet-friendly option on our way to Ottawa from Calgary. And with easy access to green space -- including a little fenced dog park for the four-legged. Four paws up!"

Reviewed on Jul 29, 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! (2,160 reviews)
"The walk-in showers were fantastic. Room was very spacious."

Reviewed on Jul 30, 2025

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Victoria Inn Hotel and Convention Centre Winnipeg
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! (1,000 reviews)
"We loved our stay but the bathroom could use an update. I didn’t appreciate being charged twice for the pet cleaning fee. We had two small dogs travelling with us. Most hotels only charge one fee for both dogs. Otherwise, the staff were wonderful and the location is great. There’s a lovely dog park ..."

Reviewed on Jul 29, 2025

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The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
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! (2,250 reviews)
"Close of the airport"

Reviewed on Jul 30, 2025

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Lakeview Signature, Trademark Collection by Wyndham
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! (1,304 reviews)
"I likw it"

Reviewed on Jul 29, 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! (1,042 reviews)
"Everything was great, except our room had a strong musty smell to it, our friends room on another floor did not smell. We told the front desk, but nothing noticeable was done."

Reviewed on Jul 27, 2025

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Alt Hotel Winnipeg
Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
1415 Regent Ave W, Winnipeg, MB
Stay at this 3-star eco-certified hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,241 reviews)
"Had a great experience there, room was very clean, check in very fast, comfortable bed, staff was courteous and helpful"

Reviewed on Jul 31, 2025

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Canad Inns Destination Centre Club Regent Casino Hotel
See all 511 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.