Austria and Prague 2019 - A Tale of a Confusing Beginning and Travel Luck

So this was our plan, in order to make the airfare affordable we were to fly to Lisbon, layover 6 hours then continue to Vienna. There we would spend one day and two nights. We would continue by train to Salzburg, where we would stay for two nights. Then we would end our trip with three nights in Prague, a place we had discussed visiting for the better part of ten years.

The night before our departure we received a rather confusing text message regarding our flight having been delayed. The next morning we checked Air Portugal's website and it reported the flight leaving at its scheduled time. So, luggage in hand, we ordered a UBER and headed towards O'hare.

The driver's GPS had him wind through a number of the neighborhoods on Chicago's north side, scenic but not particularly efficient. En route we received an email telling us our 6 p.m. flight was delayed seven hours. It was now scheduled to depart at 1 a.m. The Air Portugal app still listed the flight leaving as originally scheduled. We continued to O'Hare. Upon arriving at the airport we discovered that our flight to Lisbon was, indeed, delayed for seven hours which would mean we would miss our connecting flight to Vienna. Questions were mounting. Would we have to scrub Vienna from our plans altogether? Would we be paying for a hotel room we wouldn't be using  if we were further delayed?

We got in line at the Air Portugal counter with several other concerned and confused flyers. After waiting an hour Air Portugal employees appeared. A young man in a soiled white dress shirt said "Oh, your connecting flight will be leaving before this one arrives." We dryly informed him that we were aware of this. He pushed a few buttons on his keyboard and proclaimed "There is a non stop to Vienna on Austria Airlines that leaves at 4:30 and arrives in Vienna at 8:30 a.m." After pushing a few more buttons he handed us our passports and directed us to the Air Austria desk where they would issue our boarding passes. It was now 3 p.m.

So, in summary, our flight that was scheduled to leave at 6 p.m. with the 6 hour layover would put us in Vienna at 7 p.m. the next day. We, however, were now booked on a non stop to Vienna, which would be leaving earlier then our original flight, that would deliver us to Vienna at 8:30 a.m. the next day, ten and a half hours before our initially scheduled arrival time. Not only would we not miss Vienna we would pick up an extra day there. We rushed through security to the gate.