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I'm assuming this only works with Chicago?
That's a long drive for a beer.
Something that really pisses me off about Yelp and others is that it's now pretty much impossible to figure out where to go. Search Happy Hours on Yelp and you get a bunch of expensive restaurants that might not even be open, not $1 beers. The results are so cluttered with other non-useful data that finding the closest, cheapest, dingiest bar at 5 on a Friday is just not gonna happen.
It's the Citisearch problem. They aren't compiling information any more useful than a review and whatever checkboxes the site has decided they're going to provide. Pure data-entry sites always get swamped under the weight of their content, you have to provide something more than that. As an example, Facebook and Twitter evaded this problem by creating their own ad networks and using the data for revenue rather than just eyeballs on someone else's ad inventory.
You can filter/sort by price too on yelp but I know what you mean. A lot of it is the format of their results and how impossibly slow the maps are.

Might be solvable with a "find similar" function that lets you put in a bar you like and finds similar listings close to your location.

Unfortunately in SF $ can apparently mean $15 for a sandwich and says absolutely nothing about the price of their happy hour beer. The thing is that I really don't want similar places, I want to know which places have a happy hour and how much a beer is. More specifically, I want to know the closest place offering dollar beer.
I just searched on Yelp for restaurants near my hotel and the top rated result was a Wawa gas station.
This is cool, now I just have to move to Chicago.