Most people book an award ticket the same way they'd book a paid one: point A to point B, there and back. That's fine, and it works. But award programs have a handful of quirks that, once you understand them, let the same pile of points cover a lot more ground. Three of the most useful are the stopover, the open jaw, and the positioning flight. None of them are secret or shady — they're just underused, mostly because nobody explains them in plain English. Let's fix that.
The stopover: a free side trip hiding in your layover
A stopover is a deliberately long layover — long enough that you leave the airport and actually spend time in that city — on the way to your real destination, booked as part of a single award itinerary. Instead of treating a connection as dead time in a terminal, you treat it as a second destination.
Say your award itinerary connects through a hub city on the way to where you're actually headed. A normal connection has you in and out within a couple of hours. A stopover stretches that same connection into several days, and some programs will let you do this at no extra cost in points beyond the base itinerary — you're just choosing to linger where you'd otherwise have rushed through.
The catch: not every program allows stopovers, and the ones that do often cap how many you can take on a single ticket, or charge a modest add-on. Whether a stopover is free, limited, or unavailable depends entirely on the specific program's rules, so it's the first thing to check before building a routing around one.
The open jaw: fly into one city, home from another
An open jaw is when your outbound and return flights don't mirror each other — you fly into one city and, at the end of the trip, fly home from a different one, making your own way between the two by train, car, or a separate short flight.
This matters because a round trip on points is usually priced as a single unit, and most programs are happy to let the two endpoints differ as long as the overall itinerary still fits their rules. That means you can fly into a coastal city, work your way inland by ground, and fly home from wherever you end up — all on one award booking, at the same price as a plain round trip. Skip the open jaw and you'd otherwise fly back to your entry city just to catch your return flight, burning a day and some points on a leg you never needed.
The positioning flight: buying your way to a better starting line
A positioning flight is a separate, usually inexpensive ticket — paid for in cash, not points — that gets you from home to a different departure city before your award trip even starts. You're not trying to get anywhere interesting on this leg; you're relocating to a better launch point.
Why bother? Award availability and program value aren't evenly spread across every departure city. A route out of your home airport might be scarce, expensive in points, or routed through several connections, while the identical award seat departing from a city a short hop away might be wide open and far more direct. A cheap positioning flight to reach that better departure can save a meaningful chunk of points, or unlock an itinerary that wasn't bookable from home at all.
Stacking all three
These tricks aren't mutually exclusive. A single trip might start with a positioning flight to reach a better award departure, include a stopover on the way to the main destination, and finish with an open jaw so you don't have to backtrack home the way you came. Each piece solves a different limitation, and together they can turn one modest award redemption into a multi-city trip that would otherwise take several separate bookings.
None of these tricks change how many points you have. They change how far those points go — by refusing to waste a connection, a return leg, or a departure city that isn't working in your favor.
The cautions: what can go wrong
- Positioning flights are separate tickets. If one is delayed or cancelled, the airline has no obligation to protect your onward award itinerary — as far as the system's concerned, they're two unrelated trips. Build in a buffer of at least a full day so a delay doesn't torch the whole plan.
- Program rules vary and change without much notice. Some programs allow generous stopovers, others none at all; some treat an open jaw as free, others restrict how far apart the endpoints can be. Confirm the current rule for the specific program you're booking with — don't assume this year's rule matches what you read somewhere last year.
- Complexity adds fragility. The more moving pieces in an itinerary, the more places something can go sideways, and the harder it is to unwind if plans change. A simpler routing is easier to insure against disruption, even if it's slightly less clever.
- Award seats still have to actually be available. A stopover or open jaw only works if the segments you want exist as bookable award space on the dates you need. The trick doesn't create availability; it just makes better use of what's there.
How to actually build one
- Start with where you want to end up, then work backward to see whether a stopover city or a different arrival/departure pairing sits naturally along the way.
- Check the specific program's rules on stopovers and open jaws before getting attached to an itinerary — the rulebook, not habit or hearsay, decides what's allowed.
- If a positioning flight is part of the plan, price it in cash and compare the total cost against simply booking from home, so the "trick" is actually saving something.
- Leave real time between any separate, unprotected legs. A positioning flight landing the same day your award trip departs is a bet against weather and mechanical delays you don't need to make.
- Book the more availability-constrained segments first, since award seats can disappear while you're still deciding on the rest.
