My wife and I have been flying all over the world for years, always in the economy section. Buying a business class ticket straight away always seems to be at least triple the price of economy which I still can't justify. The other day we flew from SF to Copenhagen in business class after discovering optiontown.com and upgrading for about $450 each. What a treat. Unfortunately optiontown.com only works with a few airlines which we don't fly very often. Are there any other ways to purchase business class upgrades at a discount?

Using a miles credit card makes sense and my business charges nearly $50K/month on credit cards, but I use a 1.5% cash back card now which translates into about $750/month. Would I accumulate miles worth more than that? The other thing about miles credit cards is they're associated with a particular airline and we fly with various airlines (although we do fly United a lot).

Many carriers will allow you to upgrade at check-in or the airport, if there is space. Last time I checked US will charge 500 for a TATL.

Another option is points and cash. A poor value, IMHO.

Third you can get an award ticket. Two months of your current spend will get you to a lot of places in the world in comfort. As an example 67.5k AA miles will get you to Hong Kong one way in F on CX. Coupled with sign up bonuses you be living large.

Ultimately you have to decide if premium class travel is of more value than cash rebates.

Could you elaborate on this a little bit? Two months of spending on my 1.5% cash-back card is worth about $1500. On the United 1.5 miles/dollar card, it's worth 150k miles. Can I do more with 150k miles than I can with $1500?

Do your own math. There's no way you may fly CX from US to HK in C with $1500. However, 150K miles in the right programs can certainly do (in Gamecock's example itinerary):

Also if you had checked the award chart on UAL.com, you'd find the possibility of award tix in Business Class from SF to Copenhagen using 100K miles (Saver Award).

Now you can be the judge whether $1500 or 150K miles is more valuable.

There are many consolidators who sell business class tickets at a discount. Just Google "business class discount".

Flyertalkers routinely get well over 1.5% implied rebate on business/first class redemptions, but it depends on whether you would have been willing to pay cash for a biz seat and how much. There are literally thousands of posts here on FT about the valuation of miles.

Ah, now I'm putting the pieces together! Thanks for the link. I can rack up 200K miles in about 3 months on the 1.5miles/dollar card. That gets me two business class round-trip direct-flight tickets from SF to anywhere United or its partners fly in Europe (according to award seat availability)?

If so, that's a lot better than the $2000 cash back I would have earned over the same period of time.

How is award seat availability usually?

Perhaps this is the point where you need to log into UA.COM and start playing around with that information. Only then will you be able to make an informed descision.

Fair enough, thanks a lot to everyone for your help. I'm finally figuring this out.