I'm sure some will completely disagree but i would suggest the UK would be a good starting point for your first trip abroad...

If you can convince your reluctant SO to come along with you then you will have the benefit of speaking the same language, the food should be to your tastes (plenty of American style cuisine to be found), its 'only' 6 hours time difference to Chicago should you miss family, friends etc, 'only' 8/9 hours flight time into London, and there is plenty to do and see in London and the surrounding areas..

Obviously the main objective of a holiday/travels is to experience different cultures and to this extent the UK isnt the greatest leap, but i would suggest for your first time abroad, going somewhere that you dont speak the language especially with a reluctant traveller may be a bit of a reach...

*also as a sidenote, you will not need any form of visa to visit the UK as a tourist for <6 months, so theres minimal hassle involved in such a visit*