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1.
A somewhat small town in Northwest Indiana. It consists of some pretty cool people, and lots and lots of corn. It is also considered a suburb of Chicago. It has some nice beaches, even though Michigan has better ones on lake Michigan, and it is way way way too flat.
Hey! where are you going? I'm going to Chesterton.
by CMLB July 10, 2008
 
2.
Chesterton is a small town in Northwest Indiana, a little less than an hour away from Chicago. The towns buildings are mostly fast food related, with the exception of Broadway, a street full of small town businesses that are never hiring. The high school is full of mostly druggies, dirty kids, and skanky freshman girls, with some rare relatively cool people as well. The army is always at the high school school, which is all the rage amonst the dirty kids, but most normal people find it extremely irritating. It's no surprise that most kids are druggies, considering the only things this town has going for it is a tiny ass bowling alley that smells like cigarettes and a put put golf course.
Person 1: Wanna buy some drugs and hit on some skanky freshmen?
Person 2: Sure, let's go to Chesterton.
by Senior Burrito January 29, 2011
 
3.
Chesterton is a small town in Northwest Indiana full of corn and dirty kids. It is less than an hour away from Chicago and 20 minutes from the nearest Walmart. The school system has money for an astro-turf football field but not enough money for paper. A common hobby of most teenagers here is doing and selling drugs when they should be focusing on their education because they are higher then their grades. This town is getting worse then Portage. Please help.
What do you think of Chesterton? Man, that place sucks.
by Chestertonsucks. January 12, 2012
 
4.
Describes the act of one man or woman defecating on the chest of a man, preferably with a very hairy chest.
"Bob just gave Hubert a giant Chesterton."
by copey July 20, 2006