Sounds like most of us are in the same boat. A full blown wedding in Chicago just wasn't the way I wanted to spend $25K+. We had a goal on what we can save in a year and we're already more than 1/2 way there, it's only been 3 months. We could do the city wedding, but the way we see it, no matter what family is traveling, whether to Chicago or to Punta Cana - we LOVE the Caribbean, it's our favorite way to spend our vacation time so why not start our life off where we love to spend our time.
My parents are SUPER excited. My FI's, not so much. His sister, who's getting married 3 months before us decided to extend their trip and make it their honeymoon, his brother (who's supposed to the Best Man) spent 30 minutes complaining about every thing on Sunday. I know my FI will never forgive his brother if he doesn't come, but at this point I feel if they really love you, if they really want to be a part of your life, they will find a way. Even my aunt who's on dialysis is planning to go. My father who just found out he has cancer (a very treatable kind, fingers crossed), is planning to be there.
It's not easy planning a wedding knowing that not everyone you care about wants to be part of it, but the deeper into the planning I get the more excited it get for all of us that are there. It's going to be so special and different from any other wedding in Chicago (and we've been to a lot).
Good luck with your planning and I hope your family and his get on board! Either way, it's about the two of you and how you two want to start your life together.