oh Pitchfork

So I head to Pitchfork after work today and am greeted with the headline "Sunset Rubdown, Voxtrot, Joggers to Play Pitchfork Fest Pre-Party, More Events Announced" and I'm thinking please be while I'm there. I open up the page and find out that tix are on-sale and that it is the night I get into Chicago. The only problem is that I've already purchased Dashboard Confessional tickets for that evening. DC is supposed to start @ 7pm while Pitchfork is slated for 9pm. Do I try and catch both? I have a reeling Pitchfork will go alot later into the evening. DC does have two openers and could stretch long. The venues are 5 miles apart. Do I try and do two shows in one night on my first night in a city I've never been to? I'm leaning yes, my travel companion will make the final call. Oh, and BV says that The Roots may be playing the Windy City July 31st. If that's true I think I'll have to hit that up. This trip is shaping up to even more kickass than I imagined. Cubs game anyone?