Chicago is a world class city, but Philly isn't?
Ridiculous!
Culturally, Philly is light years ahead of Chicago and don't get me wrong, I love Chicago (my wife's home town).
Liberty Bell, Independence Hall, Ben Franklin's influences, Nations' first hospital, Nations' first medical school, Big 5 basketball, Barnes Foundation, Museum of Art, Rodin Museum, Phila. Orchestra, Phila. Ballet, Curtis Institute, etc., etc.
Food, I'd give Chicago a slight edge, maybe. Vetri, Zahav, the Fountain, Alma de Cuba, Osteria, etc. are all world-class.
Chicago's bigger and taller, but that's about it. I'll take the 17th and 18th century examples of architecture in Philly vs. the post-fire stuff in Chicago.
Lake Michigan is nice, but the Jersey shore isn't far.
As for golf, Philly is #2, only behind NYC/LI.
I've only played Medinah #3, both courses at Olympia Fields and Flossmoor, but have an invite to CGC and am very excited about playing there.
Jim Sullivan's Philly list looks good to me.
Medinah #3 wouldn't make the top 10 in Philly!