Search Cheap Flights to
Headingley

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Headingley Flights as Low as $155

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

Flair Airlines
Tue, Jun 9 - Mon, Jun 15
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Tue, Jun 9 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jun 15, priced at $155 found 1 day ago
Flair Airlines
Tue, Jun 9 - Mon, Jun 15
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Tue, Jun 9 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jun 15, priced at $168 found 1 day ago
Air Canada
Tue, Jun 9 - Mon, Jun 15
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Jun 9 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jun 15, priced at $170 found 1 day ago
WestJet
Thu, Jun 11 - Mon, Jun 15
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Jun 11 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jun 15, priced at $183 found 2 days ago
Air Canada
Sat, Jun 13 - Sun, Jun 14
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$183 Roundtrip, found 2 days ago
$183
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jun 13 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Jun 14, priced at $183 found 2 days ago
Flair Airlines
Sat, Jun 6 - Sat, Jun 20
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Flair Airlines flight, departing Sat, Jun 6 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jun 20, priced at $186 found 3 days ago
Air Canada
Tue, Jun 9 - Mon, Jun 15
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Jun 9 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jun 15, priced at $186 found 1 day ago
Air Canada
Thu, Jul 9 - Mon, Jul 13
YKF
Region of Waterloo Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Jul 9 from Region of Waterloo Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jul 13, priced at $256 found 1 day ago
Air Canada
Wed, Jun 10 - Wed, Jun 24
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Jun 10 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Jun 24, priced at $329 found 1 day ago
Porter Airlines
Wed, Jun 10 - Wed, Jun 24
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Wed, Jun 10 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Jun 24, priced at $360 found 1 day ago
WestJet
Sat, Jun 6 - Sat, Jun 20
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$365 Roundtrip, found 3 days ago
$365
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Jun 6 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jun 20, priced at $365 found 3 days ago
Delta
Tue, Jun 9 - Tue, Jun 23
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 9 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 23, priced at $366 found 1 day ago
United
Wed, Jun 10 - Wed, Jun 24
BOS
Logan Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$472 Roundtrip, found 1 day ago
$472
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jun 10 from Logan Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Jun 24, priced at $472 found 1 day ago
WestJet
Wed, Aug 19 - Sat, Sep 5
PVR
Licenciado Gustavo Diaz Ordaz Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$578 Roundtrip, found 20 hours ago
$578
Roundtrip
found 20 hours ago
Select WestJet flight, departing Wed, Aug 19 from Licenciado Gustavo Diaz Ordaz Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Sep 5, priced at $578 found 20 hours ago
Delta
Wed, Jul 15 - Wed, Jul 22
DCA
Ronald Reagan Washington National
YWG
Winnipeg James Armstrong Richardson Intl.
$610 Roundtrip, found 1 day ago
$610
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 15 from Ronald Reagan Washington National to Winnipeg James Armstrong Richardson Intl., returning Wed, Jul 22, priced at $610 found 1 day ago
American Airlines
Tue, Aug 4 - Tue, Aug 11
DCA
Ronald Reagan Washington National
YWG
Winnipeg James Armstrong Richardson Intl.
$638 Roundtrip, found 2 days ago
$638
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 11, priced at $638 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 June, 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 $155, 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 $155 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$155

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. ...
9/10 Wonderful! (1,482 reviews)
Good for the price.

Reviewed on May 15, 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! (1,006 reviews)
A good place to stay.

Reviewed on May 9, 2026

Get rates
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! (3,039 reviews)
Housekeeping came into our room, restocked the towels emptied the garbage, but did not make the beds

Reviewed on May 16, 2026

Get rates
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! (1,144 reviews)
Loved our stay. We were gratefully upgraded. Room was still smaller but beautifully appointed. Stunning space. Beds were absolutely divine. Soft mattresses and luxurious bedding. Dinner in the oval room was sub par. Service and food did not meet my expectations.

Reviewed on May 14, 2026

Get rates
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
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! (2,743 reviews)
On arrival we were told parking would be 21.00 a night. No where was it mentioned when booking. Found that to be misleading as it said self parking available but no fee mentioned.

Reviewed on May 16, 2026

Get rates
Lakeview Signature, Trademark Collection by Wyndham
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! (1,445 reviews)
excellent hotel! Very clean! super comfortable beds...but! The pillows are HARD. Excellent restaurant within the hotel, I'd definitely recommend to stay at this hotel.

Reviewed on May 15, 2026

Get rates
The Grand Winnipeg Airport Hotel by Lakeview
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 ...
8.4/10 Very Good! (1,609 reviews)
Rooms were fine and location was okay. It's quite convenient if you're arriving or departing by VIA Rail, as Union Station is just a block or two away. The breakfast is a bit hit and miss but overall pretty good. Cereals, yogurt, canned fruit cocktail and plenty of bread options including English ...

Reviewed on May 13, 2026

Get rates
Humphry Inn & Suites
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. ...
9/10 Wonderful! (1,001 reviews)
Loved the vibes

Reviewed on May 14, 2026

Get rates
Inn At The Forks
See all 649 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.