Cheap Flight Deals to Headingley MB from CA $51

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Headingley?

The cheapest prices found with in the last 7 days for return flights were CA $134 and CA $51 for one-way flights to Headingley for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Apr 17 - Sun, Apr 19
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
CA $134 Roundtrip, found 1 hour ago
CA $134
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Fri, Apr 17 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Sun, Apr 19, priced at CA $134 found 1 hour ago
OriginDestinationTravel datesFlights from*
YVRWinnipegJanuary 23 to January 23CA $137
YYZWinnipegMarch 4 to March 13CA $155
YYZWinnipegMarch 4 to March 13CA $155
YEGWinnipegJanuary 11 to January 18CA $181
YYCWinnipegJanuary 7 to January 14CA $192
LAXWinnipegJanuary 24 to January 28CA $321
ORDWinnipegMarch 23 to April 13CA $346
YOWWinnipegFebruary 5 to February 5CA $386
YULWinnipegJanuary 19 to January 21CA $435
MNLWinnipegFebruary 3 to February 17CA $1,169
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YVRWinnipegDecember 20 to December 23CA $666
YYZWinnipegDecember 21 to December 28CA $698
YYZWinnipegDecember 21 to December 28CA $698
YYCWinnipegDecember 21 to January 13CA $710
YOWWinnipegDecember 19 to January 10CA $978
LAXWinnipegDecember 21 to December 24CA $1,030
YEGWinnipegDecember 19 to December 26CA $1,062
MNLWinnipegDecember 19 to January 11CA $1,398
ORDWinnipegDecember 20 to December 24CA $1,483
YULWinnipegDecember 21 to December 24CA $1,547
*Prices include taxes and fees

Your guide to flights to Headingley, MB

WestJet, Flair Airlines fly to Headingley, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Headingley MB currently costs between CA $134 and CA $1,547. Prices vary, but for the best fares, travel in January when prices are at their lowest.  

Top tips for finding cheap flights to Headingley  

The cheapest flight for a round trip to Headingley is currently CA $134. When you search for flights to Headingley, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Headingley for nearby days.  The cheapest month to travel to Headingley is April from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Headingley 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Headingley with Travelocity 

We have top deals on plane tickets even for last minute flights to Headingley, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Headingley for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Headingley

Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
The price is CA $102 per night from Jan 5 to Jan 6
CA $102
CA $114 total
Jan 5 - Jan 6, 2026
includes taxes & fees
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! (1,267 reviews)
super friendly staff, clean, love the hello gorgeous wall!

Reviewed on Dec 15, 2025

Opens in a new windowMotel 6 Headingley, MB - Winnipeg West
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.

Luxury Hotels in Headingley

Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
The price is CA $102 per night from Jan 5 to Jan 6
CA $102
CA $114 total
Jan 5 - Jan 6, 2026
includes taxes & fees
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! (1,267 reviews)
super friendly staff, clean, love the hello gorgeous wall!

Reviewed on Dec 15, 2025

Opens in a new windowMotel 6 Headingley, MB - Winnipeg West
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.

Family Friendly Hotels in Headingley

Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

2.5 out of 5
4140 Portage Avenue Headingley MB
The price is CA $173 per night from Dec 30 to Dec 31
CA $173
CA $194 total
Dec 30 - Dec 31
includes taxes & fees
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 ...
8.8/10 Excellent! (1,004 reviews)
We had another great stay! Kids had an awesome time, parents got to relax. Will definitely be back! Front desk staff are the best also, super helpful and just wonderful!

Reviewed on Dec 13, 2025

Opens in a new windowBest Western Plus Winnipeg West
Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
The price is CA $102 per night from Jan 5 to Jan 6
CA $102
CA $114 total
Jan 5 - Jan 6, 2026
includes taxes & fees
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! (1,267 reviews)
super friendly staff, clean, love the hello gorgeous wall!

Reviewed on Dec 15, 2025

Opens in a new windowMotel 6 Headingley, MB - Winnipeg West
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.

Best Headingley Flight and Hotel Packages

Headingley flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Winnipeg South

Four Points by Sheraton Winnipeg South

3 out of 5
Price was CA $430, price is now CA $402 per person
CA $402
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Price was CA $488, price is now CA $422 per person
CA $422
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
Radisson Hotel Winnipeg Downtown

Radisson Hotel Winnipeg Downtown

3.5 out of 5
Price was CA $454, price is now CA $422 per person
CA $422
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
Don't see what you're looking for?
See all available trips from Toronto to Headingley
View all trips

Need a car after flight to Headingley?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Headingley?
Book your flight with one of the 9 airline companies that fly to Headingley. Seasoned travelers often prefer these carriers:

  • Air Canada
  • WestJet
  • Calm Air International

What airport is best to fly into Headingley?
There's no need to research flight options into multiple airports when jetting into Headingley. Winnipeg Airport is the city's only airport, and is situated 11 kilometers from all the action downtown.
Where to stay in Headingley
Lock in your Headingley accommodations through Travelocity and then start focusing on what really matters — creating marvelous travel memories. Select from 19 lodgings from which you can discover this enticing destination.If you're searching for quality accommodations in Headingley, we recommend the Motel 6 Headingley, MB - Winnipeg West and the Best Western Plus Winnipeg West. Secure a room and then start organizing all those thrilling getaway experiences.
Places to visit in Headingley
0 Seeking some more options? 0 And there's more. 0
How to get through airport security fast when traveling to Headingley
Make your flight to Headingley a little bit easier by reading over these practical security tips:

  • Have your passport and boarding pass somewhere accessible. They'll be the first things you'll be asked to produce by security personnel.
  • You'll need to stop the tunes for a few minutes. Headphones and earphones need to be taken off and put in a tub for X-raying. The same goes for items such as keys and coins.
  • Ensure your laptop and electronic devices are easily accessible. These items need to be put through the X-ray machine in separate tubs.
  • Traveling with your favorite perfume or cologne? As long as it's no greater than 3.4 ounces (100 milliliters) and it's placed in a clear zip-lock bag, you can keep it in your hand luggage.
  • Airport security personnel will likely ask you to take off your shoes prior to entering the body scanner. Choose a pair that you can slip off easily. There's nothing more irritating than having to do up your laces over and over again.
  • The list of non-permissible items is forever updating. Check with your airline's official website to understand what is not allowed on board their aircraft.

Plane Tickets To Headingley

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Headingley. Browse through our inventory to explore a wide range of cheap flights to Headingley to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Headingley as you anxiously await to exit the plane and explore what Headingley has to offer. Considering all the amazing local food and culture in Headingley, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Headingley to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Headingley without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Headingley with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Headingley today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.