We like to avoid the Midwest winters so we have been somewhat regular cruisers (usually with NCL) since 1978 on the Skyward. Memorable cruises have included the Norway. We were on the cruise prior to the unfortunate, tragic 2003 Miami boiler room explosion that was the beginning of the end for that beautiful ship. Another memorable cruise was the slow passage by Monserrat shortly after that deadly volcanic eruption. The captain narrated the best "excursion" we have ever experienced as we passed the island and viewed the somber devastation. It was like an Alaskan glacier experience but more awesome in scope.
So resuming, we had the "free air" package and flew from Chicago to Charlotte (about 1.5 hour gap) then on to Tampa on American. We had a nonstop return from Tampa on American. All went smooth including our one day in advance Park,Stay,andFly from Hyatt Regency O'Hare. For the price of a reasonable one night hotel stay we had parking provided at no additional cost for the duration in their covered parking tower. Shuttle was free to O'Hare for our morning flight.
We paid the $25 deviation fee for our Tampa flight to insure we arrived a day prior. We know that snow and flight delays can cause anxiety and frustration to embarkation. So we stayed at the Holiday Inn Westshore the night before our cruise. Shuttle provided from airport and we arranged a shuttle to cruise port for $10 per person
El Morro and Old San Juan shops