Take, for instance, Portugal: the TAP Air Portugal site offers stopover combos -- in the form of exclusive discounts on hotel rooms -- whether your flight is the one-way kind or the round kind. If you’re flying in on the new direct United line from Newark, then you’ve got stopover deals for Porto. If you’re flying in from New York (JFK) Boston (BOS) or Miami (MIA), you can find stopover deals for Lisbon, where you’ll also get complimentary wine at any of TAP Portugal’s various partner restaurants. There is, indeed an app for this (iPhone here; Android here).
Stopover deals are also especially fun if, like me, you are not super great at planning ahead. According to Hobica, most discounted airfare requires at least seven but usually 14 or 21 days’ advance purchase, and those purchases are non-refundable and non-changeable. But airfare + hotel packages have no such restrictions.
“They’re kind of secret fares in that way,” Hobica says. “The closer you’re booking to your departure date, the greater your savings are going to be.”
Even if you’re not doing a stopover, you can score discounts with combo deals
Another strategy is to look for combo deals through online booking agents like Expedia or Priceline and so forth. You can often score discounts on flights/hotels/car rentals even if you’re not looking to do a stopover, like with the “Bundle and Save” tab on Expedia, or the “Packages” tab on Kayak. Whenever you’re planning to a) fly somewhere and b) get a hotel room, start by going to the airline and hotel company sites and totaling up the individual costs. Then, shop around for combo deals to see what your savings could be if you book the two together.
“I was looking at an American Airlines flight from New York to Detroit, and the hotel package was nothing special -- a decent 3-star hotel -- but I compared the airline and hotel website prices and added up the separate costs, and the savings [as a combo] was $200,” Hobica says. “The airfare itself would have been $200 if I bought it through the airline, so you’re literally getting the airfare there for free.”
If you want to hack things even further, you don’t actually have to stay in the hotel to get the discount. If you book a combo with, say, JetBlue, where the original airfare was $300 but the flight+hotel package is $200, you can just … take that discount and run and stay in whatever hotel you actually want to stay in. I mean, don’t be rude, you should call the first hotel and tell them you’re not coming, but in terms of hanging on to that discount you’re in the clear.