Is it cheaper to fly into one city and out of another?

Yes. It saves you the cost and time of backtracking overland or paying for an extra flight to return to your original arrival city.

Should I book regional flights in advance?

If you are flying between countries like Panama and Costa Rica, yes. Prices on regional routes rise quickly as seats fill up on small propeller planes.

Booking Multi-City Flights for Central America

Use the 'multi-city' search tool on flight aggregators like Google Flights to book your entry and exit points separately rather than booking two one-way tickets. This strategy usually lowers your total cost and simplifies your itinerary if you plan to travel overland between countries.

Map your start and end points. Decide on your 'open-jaw' route. For example, fly into Guatemala City (GUA) and fly out of San Jose, Costa Rica (SJO). This avoids the need to backtrack to your arrival airport.
Use the multi-city search function. Go to Google Flights, select 'Multi-city' from the trip type dropdown. Enter your first flight (Home to City A) and your second flight (City B to Home). Do not search for two separate one-way tickets initially, as the multi-city tool will often calculate a lower base fare.
Check regional budget carriers separately. If you need to connect smaller hubs within Central America, don't include those in the long-haul search. Look at carriers like Tropic Air, Avianca, or Volaris separately, as they often don't show up on major international search engines.
Verify luggage policies. Central American regional flights have strict weight limits, often 15-20kg. Check if your long-haul booking includes a carry-on or checked bag, as regional 'Basic' fares often charge extra for even small bags.

Is it cheaper to fly into one city and out of another?: Yes. It saves you the cost and time of backtracking overland or paying for an extra flight to return to your original arrival city.
Should I book regional flights in advance?: If you are flying between countries like Panama and Costa Rica, yes. Prices on regional routes rise quickly as seats fill up on small propeller planes.