Marketing Chicago Storefront Theatre

I have a new idea for a side business that I'd really love some opinions and advice on.

To start, my mom is a travel agent in St. Louis. She tells me that she regularly puts together weekend trips for little girls, their mothers, and grandmothers to come up to Chicago and go the American Girl Store. I was thinking that St Louis theatre fans might be interested in taking similar weekend trips to see Chicago storefront theatre. It might be tricky or intimidating though to coordinate a trip like this if you weren't familiar with the storefront scene.

My plan would be to set up a small travel service to coordinate these "Chicago Theatre Weekend" trips. For a small fee I could talk to clients to get an idea of their taste in theatre, find a couple shows for them, and even recommend some restaurants for dinner before the show and bars for drinks after. You could conceivably do a Friday evening, a Saturday evening and a Sunday matinée and still get people on the road/train at a decent time to get home to go back to work on Monday.

I would have a great leg-up starting this because I would be able to coordinate with my mom's travel agency, but eventually I think that there would be a market out of Indianapolis, Louisville, Cleveland, Milwaukee, Detroit and all sorts of smaller towns in between.

What do you think? Would you be interested? Do you know anyone who would? How much would you pay for something like this?