This 2006 Jeff Garlin film shot in several locations in Chicago.
The hot dog stand with the "pirate" is:
Budacki's Drive In
4739 North Damen Avenue, Chicago, IL
(773) 561-1322
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The ice cream shop where he meets Sarah Silverman's character was located at:
3731 N Clark, Chicago, IL
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The ice cream shop is closed and it's now a Mexican restaurant.
The shot from the movie I really wanted to know existed was the spot where Garlin's character stopped to eat junk food multiple times in the film.
It appeared to be a quiet neighborhood where you could see the scoreboard from Wrigley Field. I wanted to see if it was a real spot of a faked location.
Sadly, I don't have a screenshot but the location does seem to exist right along this street:
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