I am spending 88 days in Italy, and then travelling for 2 weeks through the UK. It is surprisingly a lot cheaper to book a roundtrip ticket to Milan plus flights to and from Dublin than it is to book a flight to Milan and home from Dublin.
I will not be in the Schengen Area for longer than 88 days, but my flights will look like I am in Milan past the 90 day allowance.
Will this cause problems entering the country, or coming back to the US? Should I just cut my losses and spend the extra money on a multi-city flight?