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 $172

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

Flair Airlines
Fri, Mar 27 - Fri, Apr 10
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Fri, Mar 27 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Apr 10, priced at $172 found 1 day ago
WestJet
Thu, Apr 23 - Sat, May 9
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Apr 23 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, May 9, priced at $261 found 1 day ago
Flair Airlines
Fri, May 15 - Tue, May 19
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$263 Roundtrip, found 1 hour ago
$263
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Fri, May 15 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, May 19, priced at $263 found 1 hour ago
Porter Airlines
Fri, May 15 - Fri, May 22
YHM
John C. Munro Hamilton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$277 Roundtrip, found 6 hours ago
$277
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Fri, May 15 from John C. Munro Hamilton Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, May 22, priced at $277 found 6 hours ago
Air Canada
Sun, May 31 - Sat, Jun 6
SEA
Seattle - Tacoma Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$314 Roundtrip, found 4 hours ago
$314
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Sun, May 31 from Seattle - Tacoma Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Jun 6, priced at $314 found 4 hours ago
Air Canada
Sun, May 10 - Sun, May 10
YLW
Kelowna Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$367 Roundtrip, found 8 hours ago
$367
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Sun, May 10 from Kelowna Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, May 10, priced at $367 found 8 hours ago
Delta
Sat, Jun 6 - Tue, Jun 23
IND
Indianapolis Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$389 Roundtrip, just found
$389
Roundtrip
just found
Select Delta flight, departing Sat, Jun 6 from Indianapolis Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Jun 23, priced at $389 just found
Delta
Wed, Aug 19 - Mon, Aug 31
IAH
George Bush Intercontinental
YWG
Winnipeg James Armstrong Richardson Intl.
$424 Roundtrip, just found
$424
Roundtrip
just found
Select Delta flight, departing Wed, Aug 19 from George Bush Intercontinental to Winnipeg James Armstrong Richardson Intl., returning Mon, Aug 31, priced at $424 just found
WestJet
Fri, Apr 10 - Sun, Apr 12
YXX
Abbotsford Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$454 Roundtrip, found 1 day ago
$454
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Apr 10 from Abbotsford Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Apr 12, priced at $454 found 1 day ago
Delta
Sat, May 2 - Fri, May 22
MEM
Memphis Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$538 Roundtrip, found 1 day ago
$538
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 2 from Memphis Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, May 22, priced at $538 found 1 day ago
Air Canada
Tue, May 26 - Thu, May 28
BUF
Buffalo Niagara Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$568 Roundtrip, found 1 day ago
$568
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, May 26 from Buffalo Niagara Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, May 28, priced at $568 found 1 day ago
Delta
Wed, Jul 29 - Wed, Aug 12
ORD
O'Hare Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$616 Roundtrip, found 1 hour ago
$616
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Jul 29 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 12, priced at $616 found 1 hour ago
Delta
Sat, Aug 1 - Tue, Aug 11
MDW
Midway Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$624 Roundtrip, found 4 hours ago
$624
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Aug 1 from Midway Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 11, priced at $624 found 4 hours ago
Porter Airlines
Mon, Jul 6 - Sun, Jul 12
YDF
Deer Lake Regional
YWG
Winnipeg James Armstrong Richardson Intl.
$645 Roundtrip, found 1 day ago
$645
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Jul 6 from Deer Lake Regional to Winnipeg James Armstrong Richardson Intl., returning Sun, Jul 12, priced at $645 found 1 day ago
Air Canada
Thu, Jul 9 - Mon, Jul 27
BRE
Bremen
YWG
Winnipeg James Armstrong Richardson Intl.
$941 Roundtrip, just found
$941
Roundtrip
just found
Select Air Canada flight, departing Thu, Jul 9 from Bremen to Winnipeg James Armstrong Richardson Intl., returning Mon, Jul 27, priced at $941 just found
United
Mon, Apr 27 - Sat, May 2
LOS
Murtala Muhammed Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$1,013 Roundtrip, found 5 days ago
$1,013
Roundtrip
found 5 days ago
Select United flight, departing Mon, Apr 27 from Murtala Muhammed Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, May 2, priced at $1,013 found 5 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 March, 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 $172, 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 $172 right now, why wait?

Headingley Flight Information
Destination airport
Winnipeg James Armstrong Richardson Intl.
Destination airport IATA code
YWG
Roundtrip price
$172

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. ...
9.2/10 Wonderful! (1,397 reviews)
The check-in employee was fast and friendly, telling us there would be muffins in the morning, which was an unexpected delight. The room was bright, clean, quiet and comfortable. We will return.

Reviewed on Mar 17, 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! (1,000 reviews)
Clean room, what tonexpect from a best western

Reviewed on Mar 17, 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! (2,884 reviews)
Terrible

Reviewed on Mar 19, 2026

Get rates
Victoria Inn Hotel and Convention Centre Winnipeg
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! (1,361 reviews)
Only ate supper there which was great. Went back to room as had early morning flight. Would stay there again and would highly recommend this hotel.

Reviewed on Mar 20, 2026

Get rates
The Grand Winnipeg Airport Hotel by Lakeview
Alt Hotel Winnipeg

Alt Hotel Winnipeg

3 out of 5
310 Donald Street Winnipeg MB
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,202 reviews)
Very clean rooms. Helpful staff

Reviewed on Mar 19, 2026

Get rates
Alt Hotel Winnipeg
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! (1,197 reviews)
Was a nice experience for the kids! Will be returning.

Reviewed on Mar 19, 2026

Get rates
Birchwood Inn, BW Premier Collection
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! (1,082 reviews)
Beautifully restored hotel. Lovely rooms. Staff goes above and beyond to make your stay perfect Favourite hotel in Winnipeg. Such a great location

Reviewed on Mar 17, 2026

Get rates
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
1824 Pembina Hwy Winnipeg MB
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (1,219 reviews)
We were satisfied - one thing which would have been good was to have a water bottle filling station.

Reviewed on Mar 18, 2026

Get rates
Canad Inns Destination Centre Fort Garry
See all 603 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.