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I'm traveling Toronto -> Chicago -> Tokyo -> Havana -> Toronto, all immediately after each other.

Skyscanner and Google Flights both (surprisingly) say that it's CHEAPER to do three separate 2-way flights:

  • Toronto <-> Chicago
  • Toronto <-> Tokyo
  • Toronto <-> Havana

I would be willing to pay a bit more for 4 one-way tickets than the 3 two-way tickets, and this would also be better for the airline (Air Canada or United) since they would have to give me 4 boarding passes rather than 6 (!!). However, where would I even begin if I wanted to negotiate such a deal?

user1271772
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1 Answers1

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However, where would I even begin if I wanted to negotiate such a deal?

Nowhere. There is no such thing as 'negotiating' with an airline, unless you're:

  1. Getting bumped off an overbooked flight
  2. Booking tickets for 50+ people at once
  3. Working for a corporate sales office that handles tickets for a big organization

So forget it and go for hidden city ticketing or any other viable option on your route.

JonathanReez
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