Our group has done this the past two trips (both ways)and it was really easy. We fly Southwest going down to SJU then this trip we flew Intercaribbean to EIS. We got the SJU-EIS for $99.00 each way. After we landed in SJU we got our bags and headed upstairs to check-in for Southwest. We had TSA precheck and it was really easy. Coming back it was also very easy. A helpful airport employee showed us an elevator after we went through customs and got our bags and it took us right to the check in area.

In Wichita it is very tricky to make the trip in one day for an affordable price. We have always had best luck on Southwest for what we need price wise. There is an extra flight in there that some wouldn't like but we have always made it down there and home on southwest.