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You will have no problem at all. I have flown to several countries from Costa Rica and never have any problems.
Matt
This should not be a problem. We have many students that go to multiple locations when learning Spanish at our schools: http://www.spanishabroad.com
The key thing is you may need your flights all purchased in advance so you can show customs that you have an arrival and departure pre-arranged. Be sure to check with the airline or your closest consulate to see if this is the required procedure.
dytica
no, no problem at all
cheap_charlie_london
In general a US citizen can fly from Costa Rica to any other country provided they meet the entry requirements for the other country. The best place to check that is your local consulate for each country or your government provides a good source. Here's their info for Costa Rica:
http://travel.state.gov/travel/cis_pa_tw/cis/cis_1093.html
All the places you can fly to from San Jose are listed here:
http://stopoverflightscentre.lowcostlux.com/sjo/cheapflights.php
One thing to watch with CR is the requirement for a yellow fever vaccination if you have been to some south american countries. For example you need one to enter if you have been anywhere in Peru even though only a small zone has yellow fever issues. You can still transfer at the airport without a problem if on your way back.
Check with the CR embassy for their latest info on that.
Pure Vida
Yes. Absolutely.
AttorneyKearney
Yes, you can, there is no problem traveling to either country, you will sign a piece of paper on the plane which will be your tourist visa good for three months.