Harry Caray's Steakhouse is cool, at the bar you are below street level but the way the windows are set up all you see are legs walking by on the sidewalk, kinda like Houston's in mid town Manhattan. Great homemade potato chips to have with a cold beer. Wrigleyville has many cool places to barhop before and after the game. I haven't been in a while, but Chicago had some pretty good street festivals on the weekends. Last time I was there I enjoyed the River North Festival, live music, food and drinks.