Let's Make a Deal. Here
Are Some New Rules.
THURSDAY, NOVEMBER 21, 2019 -- Here's what I've learned over the many years we've been together in this little slice of Cyberspace: Business travelers do a lot of planning for the next year's leisure trips between Thanksgiving week and the days before the Christmas rush.

Let me offer my current best thinking on booking some good 2020 holidays during the next few weeks. Some of this you may know. Some of this goes against what used to be called the accepted wisdom. And some of this you should have already known. But no recriminations. Let's just score some real bargains while less wily travelers pursue the phony-baloney Black Friday deals.

Remember when the airlines (and hotel chains) took out newspaper ads listing sale prices? Remember when they put up promotional pages on their Web sites? Yeah, that doesn't happen much anymore. The reason: The Transportation Department essentially told airlines that ads or Web site promos of prices must be backed up with at least 5 percent of inventory. The airlines don't want to do that--or run afoul of DOT rules. So now they drop prices--domestic and international--on a tactical and largely unpublicized basis. Certain days, certain flights, select routes, very tailored prices. Very granular stuff. That makes it hard for journalists like me to tip travelers like you to a fare sale on the Steals & Deals page because the entire concept of overarching public sales is basically obsolete. What's it mean? You're gonna miss out on some terrific low prices because they came and went without announcement or promotion. What to do? Be more flexible. Move days and times around when you search for fares. Be less rigid about when you can travel. Poke around airline and hotel Web sites. Certainly use tools like ITA Matrix and those monthly low-fare finder ribbons of which the airlines are now so enamored.

As flyers have wisely deemphasized frequent flyer programs and stashed more credits in bank plans such as Amex Membership Rewards, Chase Ultimate Rewards and Citi ThankYou, the more financial institutions have tried to get us to book with them. The lure is often that our points are worth more at the bank's proprietary travel-booking service. Sometimes that's true. But often it's not--especially if you are booking an independent hotel, something the bank programs' booking sites often emphasize over chain properties. Just last week I stumbled on a great, unbranded suite hotel in Lisbon and decided to book with Chase points. When I got to the Chase site, however, its cash price for rooms was 25 percent higher: US$1,200 for a five-day stay compared to US$900 booking direct with the hotel. That essentially negated the supposed 25 percent bonus I was getting if I booked using my points at the Chase site. As I continued to check independent properties at Chase and Amex, nightly rates were routinely $25-$50 higher than booking direct. I ended up booking my Lisbon stay for cash directly with the hotel. That's a win: Not only will I get 1,800 points for charging the hotel payment to my Chase Sapphire Preferred, I can get a $900 statement credit by cashing 90,000 points. That is thousands of points less than Chase was charging to book the hotel for points based on its inflated $1,200 price.

More and more international carriers now offer a free stayover/stopover in their hub cities if you book a connecting flight. That's true even if you book coach. The stayover programs allow you to spend up to a week in the hub city (or anywhere) between flights at no charge. It's a cool way to squeeze more holiday into your holidays. Many airlines also offer free perks--tours, restaurant discounts, hotel deals--as part of their hub city stayover plans, too. If you've been around long enough, you'll recall that "stay-on-the-way" schemes were once common with international carriers. Their revival--you can find them on carriers from Icelandair and TAP Air Portugal to Japan Airlines and Royal Air Maroc--is a valuable perk too few otherwise savvy travelers are using.

We're in an extended period of divergent airline pricing: International business class fares are through the metaphoric roof while coach prices are at record lows. There are about a half-dozen reasons for the dichotomy, but every problem is an opportunity. Create your own business class by buying two coach seats--or three if you're traveling together. Hell, why not buy an entire row of four or five seats in the center section of a widebody? Even five coach seats often will be cheaper now than a single business class ticket. The trick? Make sure the airline knows what you're doing. Don't book on your own. Call the carrier and explain so you can book properly and have them enter the appropriate codes and generate the proper ticketing. Or have a good travel agent take care of it for you. Is even an entire row of coach as comfortable as business class? Of course not. But it's way cheaper--and it's way better than squeezing yourself into one seat.

When airline code-shares were new, each partner priced seats separately and it was common for one carrier to charge more than the other on the same flight. But as immunized joint ventures and "metal-neutral" arrangements meant airlines shared the total revenue generated on a code-share flight, price differences largely disappeared. That isn't a universal rule, however. Double-check the prices offered by both sides of a code share. Mister Meatball recently discovered it was several hundred dollars cheaper to book premium economy seats on an Air France-operated flight under its Delta code than Air France was charging on its own Web site.

Travelers naturally think linearly. We want to go point-to-point and tend to consider only the point-to-point price. But airlines price dynamically. There are hub-based price wars on domestic flights and wonky price disparities based on which international hub you use on an itinerary. And even in these days of ubiquitous code-sharing, not every carrier serves your airport. If you're finding a point-to-point price too high, consider booking over another hub. Or book a "self-connect" itinerary where you use two carriers to complete a trip. A roundtrip on one airline to an intermediate point and a second roundtrip between the intermediate point and your final destination might be substantially cheaper than a point-to-point roundtrip. Learn how to self-connect--carry on or remember to leave enough time to claim and recheck bags--if the two carriers don't interline or won't interline on separate tickets.

U.S. carriers are so determined to "monetize" first class cabins rather than award free upgrades to elite flyers that they have reduced the cash price of seats up front. You can often book in first for not much more than coach. Even if you don't, airlines have become extremely aggressive selling "TOD" (tens of dollars) upgrades either at check-in or at other touch points before departure. Check out the offers. You'd be surprised how few dollars an airline will take to divert an upgrade from an elite and sell it to you instead.

Hotels haven't yet monetized their suites as effectively as airlines are filling first class. Hotels are still largely awarding them--well, standard suites--to their super-elites. But that doesn't mean you can't buy your way into an upgrade for a few dollars at check-in. It doesn't ever hurt to ask how much it'll cost to get into that larger room. You'll be surprised how flexible a well-run property can be on pricing their best accommodations when the clock is running down and the room may go empty.