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How about a sporting event (like a Cubs game)? Comedy Club? Racetrack outing?
Happy hours might be good for initial get-togethers but you need some larger event in the works to sustain interest.
I like the idea of getting together with a sorority alum group. Our Windy City Club does a lot of events downtown and I'd imagine most groups have a lot of younger members in Chicago as well. Trust me, not all sorority alumnae clubs are little old blue-haired ladies who go to tea!
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