One Simple Insight Helps You Time Your Upgrades and Increase Your Success Rate

One of baseball’s greatest hitters of all time was Wee Willie Keeler, who introduced the ‘hit and run’ play to the game when he was a member of the Baltimore Orioles. It was his 44-game hitting streak that Joe DiMaggio broke. It was his record of 8 consecutive seasons with 200 hits or more than Ichiro Suzuki broke.

His batting advice was simple: “Keep your eye clear, and hit ’em where they ain’t.”

That’s also some of the best advice for upgrades. Pay attention, and travel where and when other travelers ain’t.

  • Whether you want an upgrade on a flight or at a hotel, you’re looking for a seat or room that would otherwise go unsold.

  • So you want to avoid paying customers, and where there’s the most competition for upgrades.

At hotels, the keys are:

  • Shoulder season. When a location is still nice, but fewer people go there, hotels are less crowded and there’s both fewer paying premium guests and less competition for upgrades.

  • Start of week or middle of week checkin at resorts. When you’re checking in matters. If you’re arriving when everyone else is, you’re competing with many other guests for a room. Everyone may check out on Sunday (or Monday) so you want your arrival to be Monday through Wednesday… not Thursday or Friday when everyone else’s trips begin.

  • Short stays. An upgraded room needs to be available for your entire stay in order to be assigned the room. Plus hotels want to sell their premium rooms, not tie them up. If you’re staying for a night or two they’re going to be more willing to give you a room, and it’s more likely the room will be available, than if you’re staying somewhere for a week.

  • Lots of suites relative to total rooms. A hotel with 80 suites is an easier upgrade than one with 8. It’s not just the number of suites that matters, it’s the percentage of rooms that are suites. If 20% of a hotel’s rooms are suites, you just need to be in the top fifth of most important guests during your stay.

  • Two Bedroom Villa at the Conrad Koh Samui

    For airlines, the keys are:

  • Stay away from premium routes with limited capacity. People actually pay for business class between the US and Sydney. London is a premium route, but from New York there are tons of flights, check out early evening London – New York flights if you want to clear an upgrade.

  • Stay away from the highest status upgraders. Pre-pandemic this was easy, you’d just avoid flying when most business travelers do. That meant Monday morning first flight and Thursday and Friday afternoons between 5 and 7:30pm. Things spread out a little bit more down but you still want to focus on Tuesdays, Wednesdays, and Saturdays and middle of the day.

  • Fly during the holidays. There are fewer business travelers on the road. That doesn’t make upgrades easy with full flights, but there are fewer people with status competing for what empty seats up front there might be.

  • American Airlines Domestic First Class

    One clue for both airlines and hotels is price. When a hotel’s price is high, it’s likely in high demand and therefore full. When it’s selling at a discount that doesn’t just mean you can get a deal, it means you’re more likely to get both a deal and an upgrade.

    The same is true for airlines’ US domestic flights. When a flight is cheap close to departure there’s a good chance upgrades will be easier to come by as well.

    Internationally though what you want to check is the spread between economy and business class fares. During the holidays economy often gets more expensive while business class gets cheaper. That’s because business travelers aren’t filling the forward cabins, but leisure travelers are packing in the back. Upgrades are more likely, but it’s also a time when it may even be worth coming out of pocket — where paid business class may be a few hundred dollars more than coach, rather than quadruple or quintuple the price. The absence of long haul business travelers over the past two years doesn’t really change this.

    If you’re positioning for an upgrade you’ll still need a justification for it — status, or spending miles or other instruments — but this can make those strategies more likely to succeed.

    Traveling where and when they ain’t can help you get both a good deal and make an upgrade more likely. It can improve your travel batting average, and land you in the frequent flyer hall of fame…

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