I would recommend going to Dublin from ORD and connect in Dublin to Aer Arran who fly DUB - GWY. A travel agent should be able to get you an interline ticket or else buy a separate ticket on www.skyroad.com. AT DUB you will clear immigration - depending on your ticket you may have your bags cleared to GWY. At worst you will lose about 300 miles RT on the DUB - GWY legs

Aer Arran are a small efficient airline on the Ryanair model - they operate ATR turboprobs and flight time to GWY is about 40 mins. The airport is very convenient for most of the industrial estates/business parks in Galway

Let me know how you get on with the ORD Evip upgrade as I plan to fly that a lot this year and have 8 to burn...