Originally Posted by
ftnoob
(Separate reservations may, however, increase the difficulty related to checking bags through to the final destination.)
It shouldn't. All you'd have to do is show your two BPs (or two confirmation #s).
Two things to note about checking bags if you have two different confirmation numbers. One: show up a little earlier. You'll actually need to stand in the line and see the real counter agent--the kiosk won't do it. Two: make sure the agent deletes the standby leg on the original PNR.
They'll add a standby leg on the first PNR to check a bag, so PNR #1 would read MDW-DEN-SNA, with DEN-SNA showing "standby." If they don't delete this, there can be some confusion when you get to your stopover airport. I do this all the time and normally can price tickets out to be roughly the same cost, or slightly more (~$10). Well worth it in my book. If I can save some money and get an extra segment, then even better!