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 $142

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

Air Canada
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$142 Roundtrip, found 10 hours ago
$142
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $142 found 10 hours ago
Flair Airlines
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$143 Roundtrip, found 10 hours ago
$143
Roundtrip
found 10 hours ago
Select Flair Airlines flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $143 found 10 hours ago
Air Canada
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$147 Roundtrip, found 10 hours ago
$147
Roundtrip
found 10 hours ago
Select Air Canada flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $147 found 10 hours ago
WestJet
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$147 Roundtrip, found 10 hours ago
$147
Roundtrip
found 10 hours ago
Select WestJet flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $147 found 10 hours ago
Porter Airlines
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$147 Roundtrip, found 10 hours ago
$147
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Fri, Sep 11 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $147 found 10 hours ago
Air Transat
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$179 Roundtrip, found 10 hours ago
$179
Roundtrip
found 10 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 $179 found 10 hours ago
Flair Airlines
Mon, Jul 6 - Thu, Jul 9
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Flair Airlines flight, departing Mon, Jul 6 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Jul 9, priced at $302 found 4 days ago
Delta
Wed, Sep 9 - Sun, Sep 13
PHX
Sky Harbor Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 9 from Sky Harbor Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $368 found 1 day ago
WestJet
Sun, Sep 27 - Sun, Oct 11
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$404 Roundtrip, found 15 hours ago
$404
Roundtrip
found 15 hours ago
Select WestJet flight, departing Sun, Sep 27 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Oct 11, priced at $404 found 15 hours ago
Delta
Wed, Sep 9 - Sun, Sep 13
PHX
Sky Harbor Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$442 Roundtrip, found 1 day ago
$442
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 9 from Sky Harbor Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $442 found 1 day ago
WestJet
Mon, Jul 6 - Thu, Jul 9
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$622 Roundtrip, found 4 days ago
$622
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Jul 6 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Jul 9, priced at $622 found 4 days ago
American Airlines
Fri, Oct 2 - Wed, Oct 14
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$631 Roundtrip, found 3 days ago
$631
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Oct 2 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Oct 14, priced at $631 found 3 days ago
United
Wed, Sep 9 - Sun, Sep 13
PHX
Sky Harbor Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$645 Roundtrip, found 1 day ago
$645
Roundtrip
found 1 day ago
Select United flight, departing Wed, Sep 9 from Sky Harbor Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Sep 13, priced at $645 found 1 day ago
China Airlines
Thu, Feb 25 - Thu, Mar 18
MNL
Ninoy Aquino Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,146 Roundtrip, found 1 day ago
$1,146
Roundtrip
found 1 day ago
Select China Airlines flight, departing Thu, Feb 25 from Ninoy Aquino Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Mar 18, priced at $1,146 found 1 day ago
All Nippon Airways
Thu, Feb 25 - Thu, Mar 18
MNL
Ninoy Aquino Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,276 Roundtrip, found 1 day ago
$1,276
Roundtrip
found 1 day ago
Select All Nippon Airways flight, departing Thu, Feb 25 from Ninoy Aquino Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Mar 18, priced at $1,276 found 1 day ago
Air India
Tue, Jun 30 - Mon, Jul 20
HYD
Rajiv Gandhi Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,829 Roundtrip, found 16 hours ago
$1,829
Roundtrip
found 16 hours ago
Select Air India flight, departing Tue, Jun 30 from Rajiv Gandhi Intl. to Winnipeg James Armstrong Richardson Intl., returning Mon, Jul 20, priced at $1,829 found 16 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 September, 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 $142, 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 $142 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$142

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! (1,555 reviews)
"Nothing special! Dry muffins for breakfast! Keep driving."

Reviewed on Jun 28, 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! (1,002 reviews)
"Loved the stay."

Reviewed on Jun 27, 2026

Get rates
Best Western Plus Winnipeg West
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! (1,198 reviews)
"The rooms are extremely cold and the heat took forever to kick in and when it did it only warmed up a few degrees. The beds were very lumpy and uncomfortable. Walls are paper thin I could hear my neighbours phone conversation. I wasn’t impressed with the view of a wall and dog relief area but they ..."

Reviewed on Jun 27, 2026

Get rates
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
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! (3,123 reviews)
"Top marks for this hotel! And I've been to many."

Reviewed on Jun 27, 2026

Get rates
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
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! (2,805 reviews)
"."

Reviewed on Jun 28, 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! (1,477 reviews)
"It is very conveniently located across from the airport and has a very good restaurant, The Blue Marble. It is also attached to the Lakeview Hotel which has another restaurant with great food as well."

Reviewed on Jun 28, 2026

Get rates
The Grand Winnipeg Airport Hotel by Lakeview
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! (1,003 reviews)
"Always stay here near the water !! Great spot"

Reviewed on Jun 27, 2026

Get rates
Inn At The Forks
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! (1,211 reviews)
"Ups: Clean and spacious room. Amazing spot for families in terms of their rec space and restaurant. Downs: We had an odd noise complaint when we were just conversing and a few laughs. The next morning I could hear every single word the neighbours were saying and realized that there's floor gaps between ..."

Reviewed on Jun 27, 2026

Get rates
Birchwood Inn, BW Premier Collection
See all 658 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.