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Pie Hole Pizza Joint, 737 W. Roscoe St.; 773-525-8888 (Red, Purple, Brown Lines-Addison or Belmont)

What's a late-night eating compilation without a pizza place? Pie Hole, in the midst of Boystown, offers one-of-a-kind pizzas such as the Angry Pesto, featuring a sun-dried-tomato pesto sauce, and the foul breath-inducing Bad Date, complete with garlic, onions and anchovies. Open until 3 a.m. weeknights and 5 a.m. weekends; visit for the all-you-can-eat special Wednesdays and karaoke Thursdays.
Chicago Tribune
Pie Hole Pizza Joint, 737 W. Roscoe St.; 773-525-8888 (Red, Purple, Brown Lines-Addison or Belmont) What’s a late-night eating compilation without a pizza place? Pie Hole, in the midst of Boystown, offers one-of-a-kind pizzas such as the Angry Pesto, featuring a sun-dried-tomato pesto sauce, and the foul breath-inducing Bad Date, complete with garlic, onions and anchovies. Open until 3 a.m. weeknights and 5 a.m. weekends; visit for the all-you-can-eat special Wednesdays and karaoke Thursdays.
Chicago Tribune
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In the wee hours that straddle Chicago’s late-late nights and early mornings, the streets and sidewalks fill with an eclectic mix of commuters. Some have just finished a late shift, while others are on their way to an early one. Some have endured a multi-bar blitz on the liver, while others are simply killing time in the midst of an episode of insomnia.

Whatever the reason for their verticality, many late-nighters have one goal in common—satisfying their odd-hour hunger. The city has several notable late-late-night dining establishments with diverse cuisines. The best offer one-of-a-kind atmospheres and convenient access to public transportation. –Joe O’Donnell