The savings can be great, but the risks must be weighed…

Weaving tickets booked with points into deals booked with cash, or just buying tickets with cash, one city at a time can save tons of money versus buying a round trip or multi city ticket in one go.  But any great deal can be instantly invalidated if you’re forced to part ways with $5,000, just to reach your final destination. There are plenty of ways in which booking separated one way tickets, or weaving points and cash deals together can save – but it’s important to note they can also cost big time. Here’s how to avoid issues and weigh your options when you book trips with multiple itineraries.

First, The Rules

When connecting to flights within the same airline alliance, or in some cases even the same airline, tickets booked separately are generally not covered if you miss a flight. Airlines have become increasingly strict with refusing assistance to passengers unless the missed flight was booked together with the flight that caused you to miss your flight. Therefore, caution is the key word. Confirm as many details as possible as to how your airline or alliance handles missed connections, and be sure to specify separate itineraries when doing your research. According to View From The Wing, American Airlines (and possibly all OneWorld airlines) should still honor reservations, even in the case of separate bookings.

Potential Baggage Hiccups

Many airlines now choose to interline bags onto other airlines, even if agreements exist which encourage them to do so. This is airlines revolting against customers not booking journeys in their entirety, and instead piecing them together. When this happens, what may seem like a simple connection can turn into a nightmare, when passengers are unwittingly forced to clear immigration, grab their luggage, bring it from arrivals to departures, wait in line for check in, re clear security and then make a flight. Be crystal clear before departure if an airline will send your bags to their final destination, if you’re traveling on multiple itineraries.

What Happens If You Miss

If you miss a flight on a non connected itinerary, say… Boston to Paris on Air France using points, and then Air France from Paris to Rome using cash, you are entitled to nothing. An airline may choose to be helpful where able, especially for frequent flyers, but there’s no obligation if you are traveling on two different record locators, confirmation numbers, ticket numbers or itineraries. This can lead to paying $1000’s for last minute tickets. The further your remaining flights, the more you’ll generally be forced to pay.

Savvy Planning

Many travelers overlook the benefits of extra, extra safe connections. And when you’re booking separate tickets – you can stopover as long as you want. Why stress about a 1 hour connection in Tokyo when you could build in a 18 hour connection, check your bags in early (some airlines) and explore Tokyo for the day. You get to avoid buying a hotel for the night, but also get to enjoy a day and night in the city. If the only safe connections involve an overnight hotel stay, calculate the cost of the hotel into any potential savings.

Just A Reminder

This is just a friendly reminder, which many people overlook in the excitement of trip planning. I once flew the long way home from Melbourne to London with my wife, going from Melbourne to Sydney, Sydney to Tokyo, Tokyo to San Francisco, San Francisco to Los Angeles and Los Angeles to London – all in one go. All was fine until I reached San Francisco, where a Delta agent had made an error and changed my flight during a previous phone call. I foolishly never looked to confirm the changes were correct, and missed my flight from San Francisco to Los Angeles. I was forced to book an expensive last minute ticket to get from San Francisco to Los Angeles, for which only seat was left. Had I missed that flight, I would’ve had to buy a walk up ticket to London, which would easily have cost $3,000. Yikes.

Have you ever been caught out by missed connections?