re: Cities / Places that you've been and enjoyed, but no desire/need to go back

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By all means, please explain how my personal opinion on Chicago and Paris are wrong.

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You self-admitted to doing the "touristy stuff," which is all downtown. Chicago is a neighborhood-centric city - no one stays in The Loop past their 9-5. Go into the neighborhoods and you'll get a real dose of how Chicagoans live, eat and drink. Summertime in Chicago is incredible, especially with street fests every weekend (i.e. Wicker Park Fest, Andersonville Midsommarfest, Pilsen Fest), rooftop parties, outdoor concerts and music fests (i.e. Northerly Island shows, Windy City Smokeout, Lolla, Riot Fest), boating on Lake Michigan (i.e. Playpen), etc.

Not that I expect everyone to love Chicago, but it just doesn't sound like you know where to go outside downtown. Little more difficult to find that information as a weekend visitor.