Biggest problem with the JL routing for me is the mid-con red-eye to get to ORD. My body would be hurting when I got on the JL plane -- not sure I could enjoy the food and drinks
You should be able to have up to a 23 hour 59 minute connection at ORD... Any way you can get an earlier SFO-ORD the day before and spring for a hotel in CHI or, worst case, out at the airport?