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Awesome weather coupled with a TON of shit going on all the time from music festivals, food fests, free concerts and the like. There is always something to do. Not to mention the fact that the city of Chicago is one of the only cities in the country to be planned with an open lakefront, meaning the city itself doesn’t butt up against the water, leaving a ton of beautiful parks and beaches open to Lake Michigan. You can chill on the beach with a beautiful view of the skyline, all day son.
tl;dr tons of shit to do, also fresh-water ocean.