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Find the cheapest complicated flight?

Im in Liberia Costa Rica (LIR) i need to get to Moscow, then Toronto and return Liberia. I can get to Miami cheap on Spirit Air, so lets start from a MIA to Moscow, unless there is a super cheap connection somewhere else. I could always drive to San Jose (SJO) if there is a cheap connection to Moscow. Dates are as follows and are flexible by a few days. July 25 to Moscow, Aug 3 to Toronto Aug 25 back to Liberia (LIR) or (SJO)..preferably (LIR). 5 points, tough one..be creative. Thanks and of course 5 points.

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2. A couple of holes in your approach: San Jose is about 3000 miles from Miami unless you're talking about the San Jose in Costa Rica (that's the airport code you gave) so I'm not sure how that detail fits in. Spirit is in contract negotiatins with their pilots and have already had one strike, with others planned, so I would be a little nervous about flying them when the trip is part of such a large, complex itinerary. They do not have partner agreements with most other airlines so if your flight is cancelled due to a strike, you'd be on your own to rebook which means paying last-minute top-dollar fares with another airline. You can shave some money off of your fare by trying to fly to Buffalo, Syracuse or New York City rather than Toronto, then taking a bus, train or car to Toronto. Most International flights in/out of Canada are subject to a fuel surcharge which can be a couple hundred dollars US each way. Also check fares in and out of Ottawa as well as Toronto, as the two cities are not far apart by train or car, about a 5-hour drive. Ottawa is Air Canada's focus city and they're running some good sales right now. While I don't have the time to compile an actual itinerary for you, here's how I'd do my research: Start with Moscow and work your way back. What is the cheapest way to get from the US to Moscow? You can get to Toronto fairly easily from almost anywhere in the Eastern US. Once you have your itinerary from the US to Moscow, you can begin working on how to get to the US from Costa Rica, and the trip from the US (wherever you start your Moscow trip) to Toronto has so many affordable options that you will be able look at.