When you book travel with points, you usually face two doors: the card travel portal, or booking direct with the airline or hotel. Both are legitimate, and the right choice depends on the trip, not on loyalty to one method. The portal's advantages and the direct booking's advantages are almost mirror images of each other.
The portal wins on earning and flexibility. A Sapphire Preferred card earns 5 points per dollar on travel booked through Chase Travel, versus 2 points on other travel, so the same flight earns more than twice as many points through the portal. Points redeemed in the portal are worth more than the one cent per point of cash back, and you can mix points and cash instead of draining your whole balance. Most importantly, the portal needs no award availability: if a seat or room is for sale for cash, you can usually buy it with points. For an ordinary economy flight or a hotel in a town your loyalty program barely covers, that freedom is decisive.
Direct booking wins on recognition and control. A hotel stay booked direct earns elite nights and hotel points and receives elite treatment at check-in, including upgrades and breakfast where your tier provides them. A portal hotel booking is a third-party booking and usually earns none of that. When something goes wrong, a direct booking means dealing with the airline or hotel itself, while a portal booking means going through the portal's help line first, which is fine for small changes and painful during a midnight cancellation.
Flights are the exception that surprises people. A flight booked through a portal is a paid ticket as far as the airline is concerned, so it earns frequent flyer miles and counts toward airline status like any other purchase, as long as your frequent flyer number is on the reservation. Hotels work the opposite way, which is why the portal is a poor fit for stays where status matters and a fine fit for flights almost always.
There is a third door that beats both for the right trip: transferring points to an airline or hotel partner. A business class seat that the portal prices at 200,000 points can often be booked for far fewer miles through the right partner program, because award prices are fixed while portal prices follow the cash fare. The catch is availability: the award seat has to exist, and you have to find it. When it exists, transfers usually win by a wide margin. When it does not, the portal is the fallback that still lets your points pay.
The decision rule is short. For flights, compare the portal price with the airline's own price and with the partner award price, then take the best of the three. For hotels where you want elite nights, points, or recognition, book direct. For hotels where none of that matters, take whichever price is lower, portal or direct. And always check the same trip both ways before you pay, because portal prices are competitive, not automatically lowest, and the difference is sometimes large enough to change the answer.