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?