Sadly, no. There are definitely entrepreneurial/startup-minded people in the Midwest, but they are scattered and not organized, there's nothing approaching the concentration of talent and events that exists in the Bay Area.
That's one of the main reasons why I'm dropping everything and moving to San Francisco in about a week to work on my startup. As much as I like Chicago, the connections and resources just aren't there yet.
So, no then? I'm pretty sure he didn't ask his question because he was unaware of the existence of flight. Your link initially led me to believe that there is actually some other conference called Hipmunk in the Midwest, but instead it was a LetMeGoogleThatForYou.com-style flight search page.
For those of you actually interested in events in the Midwest, I can tell you that we're doing some interesting things in Cleveland that I can scrounge up more information about. Nothing conference-level that I'm aware of, but events with founders and incubators are becoming more and more frequent.
I think PG hears a lot about location ("We're the YC of Alaska!", "Do we have to move if we get into YC?") and is getting tired of it. If you want to start a startup, moving to a startup hotspot will help a lot. If you want to attend cool conferences, move somewhere that frequently has cool conferences, or be willing to get on a plane for a good event.
The Midwest won't have a successful Startup School clone (at least not with speakers of this caliber) because it's not dense enough with startup people. Maybe there are enough people to make the event worthwhile in all of the Midwest, but it's such a huge area that a lot of people would still be facing very long drives or flying.
When people say "I want an event like this in <my region>", they really mean "I want an event like this within a 2 hour drive of my house, preferably closer." They don't mean "I live in Ohio and would happily travel to Kansas for this event." If someone were to announce an event like this in, say, Minneapolis, a lot of people form Indiana and Ohio would realize that that's not what they had in mind when they asked for a Startup School clone in the Midwest.
And now PG's invested in a flight comparison startup, so just as people sometimes link to http://www.justfuckinggoogleit.com/, he can link to Hipmunk to say "just fucking fly here."
I didn't mean anything quite so rude. I meant it more as invitation. Lots of the people who come to Startup School fly in to do it. That's why we have 2 weeks between acceptances and the date of the event-- so people can buy cheap plane tickets.
I think asking why Silicon Valley almost completely ignores the midwest when there is engineering talent here in spades (I'm in Chicago and we have the population and the top flight engineering schools to, I believe, merit some attention) is perfectly legitimate and saying "just go to SV" is a "let them eat cake" answer which misses the fundamental issue.
Even if the answer is as simple "YC's plate is totally full just keeping up with the SV scene" or "pg hates the cold", that would be more compelling than just a brush off and link to some plane tickets.
pg's written entire essays on the subject. But the bottom line is: if you're into startups, Silicon Valley is the best place. It'll take more than a conference or two to make Chicago a startup hub.
If you want a different opinion, read 37signals' blog and books. They're right there in Chicago.
"Why does Silicon Valley ignore the Midwest" strikes me as missing the point entirely. Regions don't become entrepreneurial by the careful attention of people from other, more entrepreneurial regions. They do it themselves. That is the point of entrepreneurship!
