When to use the Chase Travel Portal

A friend recently asked me a question:

Does it matter if I buy the flight through the Chase website or transfer the points to, say, British Airways and book on their website?
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The simple answer is: it does. With the Chase website and its Ultimate Rewards Travel Portal, your points are essentially cash, which are, depending on your card, worth 1.25-1.50 cents/piece.  If you transfer those same points to a transfer partner (i.e. United, British), you could do better or worse than “cashing in” your points.  That calculus all depends on award availability.  For example, with British Airways, you can book most domestic American Airlines first class tickets for 7,500 points plus a few bucks in fees each way.  This is usually a great deal because a ticket like that will run you around $400.  So, in effect, you’re getting around 5 cents a point. This is incredible if you think about the fact that you’re earning 3 points per dollar spent on most purchases with the Reserve card.  That’s the equivalent of 15% cash back.  #worthit. 
 
The fun thing about points and the Chase cards is that you can play around with the frequent flyer programs for Chase’s transfer partners.  To hop across the pond, I might find a terrible deal on Virgin Atlantic, but an absolutely fantastic deal on United.  It all depends on which route I am taking and timing.