Yes this trip was actually pretty well planned out until the unexpected happened. Last minute client rush required me to take large package on plane or ship it overnight. Overnight shipping was more expensive compared to Southwest $75 fee which I knew was lower cost than United. Everything went great on Southwest flying into Chicago but on the way out there was some sort of freak storm that cancelled flights out of MDW but not ORD. How this is possible I don't know since they are so close together. Since I needed to be back I booked a ticket on United at last minute (since Southwest should refund or at least give credit) which surprisingly was still a very cheap fare and headed to ORD airport. I already knew United was going to charge $200 oversize which is the reason I went with Southwest the first time but didn't expect the double oversize and overweight. If I had more time I would have just shipped it ground which is $50 but of course couldn't do that when I expecting to get on the Southwest flight until it got cancelled due to weather.

At the end I applaud United for figuring out how to make more money off someone in a bind but again the point of this post was simply to point out the "hidden" (not disclosed in a flight search) fees. I already knew about the $200 oversize vs $75 on Southwest to pick Southwest but assumed wrongly about the double charge.

Again I don't blame United, they didn't have to cut any slack and they didn't. They could have taken the stance that I was already willing to pay $325 vs $425 for 1.5 extra and the bag wasn't free but they stuck to their guns and enforced the fees like the hand of God. Something I would expect from Spirit Airlines but thought (obviously wrongly) that other "premium" airlines were more lenient.

Moral: Avoid Chicago for business. I avoid going to Chicago in the winter as it seemed every time I did the flight was delayed due to snow. Didn't expect "thunderstorms" to cancel the flight so really that was the big lesson: Chicago's weather sucks.