The problem is that you need to connect with the person who is traveling at exactly the right time. too soon and you lose mind-share, too late and it's no longer necessary. you need to figure out the delivery mechanism that works well. Maybe see if you can partner up with groupon travel destinations as an adder and offer them a split of it. so if groupon sells a hotel package in Chicago you should be offering your Chicago package. I think living social offers vacation packages too.

You can offer a few different levels of service too: default is web/you print at home. You can offer a full color printed version with the order if you want as well. logistically this is harder but it seems like more of a deal.

There is also the fandango way of doing it too. offer the ability to prepay for the tickets and take a small commission off the top for that. that's tougher to sell to the consumer because you don't have the trust relationship and might leave them stranded at the venue with no valid tickets. It would be slick to have this so that they didn't have to wait in line at all. make it opt in though and let them select what they want to actually go to see/do.

An iPhone app that has everything integrated would be great but it could also be as easy as just an interface for the pdf. If you got it into the appstore you would increase your visibility a bit especially if you target the "what should I do in x" queries with adwords that linked to a specific version of your app. you could also have inapp purchases that would download a new guide. cross selling in your apps is a good thing in this case.

pretty interesting idea. I'd probably buy the sf one if I go there ever but you have to reach me at the right time....