When we first started traveling, online tools were nowhere near as advanced as they are now. In our early days we used Priceline a few times, which was great for saving money–we used the “name your price” feature–but not so great for controlling the times of the flights. We once ended up with a 7-hour layover in Milan, and a 4AM departure from Venice. Never again.

So now, we research to get not just the best price, but the most convenient flights for us. Many search engines (including our favorite, kayak.com) allow you to specify take-off and landing times, which is great for avoiding super-early morning flights, or arriving back home at midnight.

But you might be surprised how simply comparison shopping for airfare, and being willing to think outside the box in terms of booking options, can save you hundreds, or sometimes thousands, of dollars.

Someone I know once booked a package tour, and rather than book his own airfare, asked the tour company to find flights for him. When he told me what the flights cost and that he had two layovers, I went online and quickly found that he could have saved about $1000 and had only one layover by booking it himself.

Another example: planning our trip to Morocco in 2009 and searching for a round-trip flight from Boston to Marrakech turned up flights around $3500 (for both of us). But when I started researching separate round-trip flights, i.e., Boston to Europe, then a separate round-trip from Europe to Marrakech, I realized the prices for those individual flights were MUCH less expensive. It appeared we were paying a premium to let one carrier manage our trip for us.

So we thought, why can’t we just book them separately ourselves? We really didn’t care which European city we flew through, so it took very little time to find the least-expensive round-trip at that time happened to be Boston to Madrid – around $600 each. Then, checking flights from Madrid to Marrakech, we found an Easy Jet flight for $149. Total cost for us both: $1500, rather than $3500. So, with a little searching and creativity, we saved $2000. Actually, we made Morocco a possibility, because we never could have afforded to go if we had to spend $3500 just on airfare.

(One thing to keep in mind, if booking your flights separately as above, is that you allow plenty of time to go through customs (if international) and then get to your next flight, which could be in a different terminal. This can happen even if you book everything together, but in that case the airline will have (in theory) taken into account how much time you need. Just be sure to do a little research on the airport you’re transferring in. This is another great reason to pack light.)

In terms of cost, it helps if you can be flexible on your travel dates. We have found that the lowest airfares across the board are midweek – generally Tuesday, Wednesday and Thursday. If you must fly out on a Saturday and home the following Sunday, just know that you will very likely pay more (in some cases MUCH more) for your flight. We have found this to be consistent, whether a domestic or international flight. Some search engines will let you choose a “flexible date” option, so you can see the prices two or three days before and after your target date, to compare whether you’d save more by flying a different day.

One final tip on searching for airfare generally, but especially via search engines/booking sites like Kayak, Expedia, Orbitz, etc.: there are many filtering options available, allowing you to restrict by takeoff and landing times, layover lengths, even layover airports. These are great tools for finding just what you want. However, we realized the site was hiding many flights we were interested in, because of an erroneously clicked checkbox in the filtering options. So, always check that you’re not being so restrictive with your filters you’re eliminating potentially good flights (and prices!)

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So, India. We’ll be visiting several places within the country, but the first task in planning this trip is to book the “big” flights: Boston to India at the beginning of our trip, and then home again at the end.

Because there are no non-stop Boston to Delhi flights, any travel plans involve a change of planes. And there were many, many options available, with one, two or even three stops. One bad option we saw was Boston to Newark (NJ), then a 14-hour flight to Delhi – I don’t think I want to be on the same plane for 14 hours! We pretty quickly decided that we only wanted one stop, preferably in London. This seemed most appealing to us because the two legs of the flight are similar in length, so you get a break roughly mid-way.

But most flight combos we were coming up with on Kayak.com were evening flights, both legs: an overnight flight to London, then a day sitting in the airport, then another evening flight to Delhi. So, in both cases, you’re on a plane when you “should” be sleeping, and you have a long, boring day in the airport in between. There had to be a better option.

Then we thought, what about a DAY flight to London? We have friends who took a day flight a few years ago and loved it: you fly during the day, when you’re naturally awake anyway, and arrive in the evening. The rub here is that there’s not enough time to clear Customs in London and then get on the evening flight to Delhi. But, aha: there is also a day flight from London to Delhi as well. So, an evening in London. To sleep. Like normal people.

Even better, it’s the least expensive combo we found. Serendipity, we think.

However, when we clicked on this combo on kayak.com, we were forwarded not to the airline (British Airways), but to Travelocity. Hrmph. I’m sure Travelocity is fine, but we have heard and read about some major hiccups for people when they have to make changes, and have not booked directly through the airline. We prefer to buy from the source.

So, we wrote down the flight numbers, and went to the British Airways website. But the flights we just saw were not coming up at all, as a combo. They were available as individual flights, but the price was more than double what kayak was showing. (This is the exact opposite experience of our flight to Morocco.)  Not to be defeated, a phone call to British Airways confirmed that the flights we were interested in were not a “natural combo”, which is why they were not appearing. But she could book them for us, at very close to the Travelocity price, and she waived the phone-booking fee.

Flight to & from India: check. Next up: planning out our visit, city by city. Stay tuned…