The man wants to go somewhere and he is asking a valid question. I don't think he's asking to be judged as to whether he could afford it or not, or who's paying for it for that matter. I suggested deletion for YOUR post. And at 45 years old at most, with all due respect, you should think twice about posting such a "pointless post" yourself.
Any flight out of ORD
(if you are a United flyer) should be pretty worthwhile, particularly to popular (and high load factor) destinations such as SFO
to name a few. Value-wise, your best bang-for-the-buck places to visit are the west coast cities. I fly ORD
all the time and often see deals either under or a little above $200. Of course flying from TPA
will be a little more but if you can get a flight with decent times for around $300, I say go for it. You get a good amount of miles as well for a great price.
If you're thinking international locations, flights to Asia tend to be a little pricier and there are a lesser amount of deals out there compared to flights to Europe. I fly ORD
twice a year and have never really found a great value for those routes. ORD
on the other hand might be a good option if flights ever go back down to around $700 or so.
In any case, there are plenty of options flying in and out of ORD
Its better to be on the ground wishing you were in the air than be in the air wishing you were on the ground. Fly safe!