Last updated: October 25, 2026
✓ Verified October 17, 2026. We find and share travel deals — we don’t sell them and we can’t guarantee availability. Giveaways can change or end without notice: always check the official giveaway post for the current rules before you enter. Deal spotted on Porter’s official channels and confirmed via multiple contest trackers.
Porter Airlines is turning 20 — and instead of a cake, it’s handing out 40 roundtrip flights. To mark its 20th anniversary (the official milestone is October 23, 2026), Porter is running a week-long Instagram giveaway with 20 winners, each receiving two roundtrip flights to any Porter destination — roughly a $1,800 CAD value per winner. That’s a getaway for two, on Porter, to anywhere in its network: Canada, the US, Latin America or the Caribbean.
The twist that makes this one worth entering today rather than tomorrow: new winners are drawn daily throughout the promotion. Entries submitted on the giveaway post count toward all remaining daily draws, so entering now puts you in more draws than entering on October 22. If you’ve ever wanted to try Porter’s much-talked-about service — free beer and wine, real snacks, no middle seats on many aircraft, the downtown Billy Bishop airport — this is the cheapest possible way to do it: free.
The dates that matter
- Giveaway announced: October 15, 2026.
- Ends: October 23, 2026. That’s the hard cutoff — the 20th anniversary date itself.
- Draws: daily. New winners are picked every day of the promotion, which is why entering early is the single best thing you can do.
What you can win
Twenty winners will each receive two roundtrip flights to any Porter Airlines destination — 40 roundtrip tickets in total across all winners. The prize is flexible by design: pick a Porter destination you’ve been eyeing — a winter sun escape to Mexico or the Caribbean, a US city break, or a cross-Canada trip — and bring a travel companion. Porter has grown well beyond its original Toronto–Ottawa–Montreal triangle; its network now spans Canada, the United States, Latin America and the Caribbean, with newer sun destinations in the mix.
One caveat worth stating plainly: the Instagram announcement doesn’t spell out every detail — destination restrictions, flight terms, and the exact prize-claim procedure aren’t listed. Check the official giveaway post and its rules before you count on a specific trip.
How to enter
Entry happens on Instagram, and it takes about a minute:
- Follow @porterairlines on Instagram.
- Comment on the official giveaway post with your dream Porter destination.
- Tag a friend you’d bring along — and make sure both of you follow Porter Airlines.
Multiple entries are allowed, and one entry covers all remaining giveaway days — you don’t need to re-enter daily. Contest trackers note the announcement doesn’t specify eligibility countries or minimum age beyond the usual, so confirm the official rules on the post itself before entering. (Canadian contest trackers list it as open across all provinces, 18+.)
Bonus: the VIPorter points giveaway
Porter’s anniversary generosity doesn’t stop at the Instagram giveaway. From October 15 through November 3, 2026, the airline is also giving 20 VIPorter loyalty members a chance to win 20,000 points each — one winner drawn per day over 20 days. Canadian VIPorter members who flew with Porter or redeemed points between October 1, 2025 and November 2, 2026 are automatically entered — no action needed. Twenty thousand points covers, for example, a round-trip redemption to select sun destinations in Mexico or the Caribbean (10,000 points each way, minimum), subject to availability and taxes. If you’re already a VIPorter member, you’re in the running without lifting a finger.
How I’d play it
Enter the Instagram giveaway today — not because the odds are huge (20 winners from what’s sure to be a large entry pool), but because the cost is zero and each day you wait is one fewer daily draw you’re eligible for. Tag the friend you’d actually travel with, pick a destination you’d genuinely book, and move on. Then check whether you’re automatically in the VIPorter points draw — if you’ve flown Porter in the past year, you might already be.
And a small note on honesty: this is a giveaway, not a fare sale, so there’s no “price” to compare and no booking strategy to optimize. The only strategy is entering early and entering correctly (both followers, comment on the right post, tag done). Everything else is luck.
Reminder: the giveaway ends October 23, 2026, with winners drawn daily — entering earlier means more draws. Always verify the current rules on Porter’s official giveaway post before entering; contest details can change.