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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?

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    Have you been pricing this as four one-way tickets, or a single multi-city itinerary? – Nate Eldredge May 27 '17 at 21:58
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    Unfortunately you don't have an avenue to negotiate individual tickets with mass commercial flights. Imagine the airlines would need to have an entire division of negotiators if they opened things that way. There's a benekfit to them for standardization. I use my airline miles for exactly this kind of scenario. – user57303 May 27 '17 at 22:48
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    Try a different set of round trips, like Toronto-Chicago, Chicago-Tokyo, Chicago-Havana. It might save time compare to the three you suggested, and you can arrange the timing so you don't need to leave O'Hare between the "connecting" flights. – John Zwinck May 28 '17 at 1:31
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    You are mistaken if you believe that it'd be better for the airline. See this fantastic answer travel.stackexchange.com/a/49417/4188 on How do airlines determine ticket prices?Also see the insanity I hit in travel.stackexchange.com/a/66868/4188 where Budapest-Amsterdam/Paris-Budapest can be priced as a return but Amsterdam-Budapest/Budapest-Paris can't! – chx May 28 '17 at 8:21
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    Have you tried a real travel agent, sometimes they will have "cheaper" fares. – Max May 28 '17 at 10:39
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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.

  • 1
    -1. You have made an assumption that the answer is "nowhere". Yet, you suggest there's a way to do it if I were to book 50+ tickets at once? How would I go about doing that? I don't appreciate being told to "forget it". – user1271772 May 28 '17 at 19:29
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    If you need 50 seats, ask a separate question please. As is the answer is nowhere. – JonathanReez Supports Monica May 28 '17 at 19:34
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    You cannot possibly be 100% sure that the answer is "nowhere". Someone might have an idea regarding how to do it. However, with your answer sitting there with up votes, I worry that others will think the question's answered. – user1271772 May 28 '17 at 23:00

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