Advice needed... Flight from OGG to SFO (a 757). Then SFO to ORD My connection time is 38 minutes. I am currently seated in economy row 28 but I am more then willing to pay the $74 to upgrade if it will ensure I make the connection. There is another flight that I can take that routes me through LAX that wasn't available when I booked for the same miles. However, it is available now for a $75 fee (which I don't want to pay). United assured me that I can make the SFO connection (without even knowing where I was seated).
Secondly, if I miss the connection are they responsible to put me up in a hotel if there is not another flight out. I have never seen San Francisco and this might be a good opportunity.