Photo: Michael Lazarev (Asmadeus), CC BY-SA 2.0 via Wikimedia Commons
A stunner. Chicago history lies in rest here, from the major names (Burnham, Sullivan, Field, Pullman, Mies) to the footnotes (Charles Dickens' obscure brother Augustus). Some credit Sullivan's 1890 design for the Getty Tomb as the opening act of modern architecture. (And Inez Clarke's grave is one of the most famous "haunted" spots in Chicago.) The new (and warm) office can supply a map for the grounds, which are quite large. Come with time to wander.
Graceland Cemetery is a large historic garden cemetery located in the north side community area of Uptown, in Chicago, Illinois, United States. Established in 1860, its main entrance is at the intersection of Clark Street and Irving Park Road. Among the cemetery's 121 acres (49 ha) are the burial sites of several well-known Chicagoans.
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Uptown got short-changed when it comes to beaches compared to its neighbors on the north and south, but this is what's there, a short walk east on Wilson. One bonus: it's officially Dog Friendly. The smaller Foster Beach is a few blocks north at 5200 N Lake Shore Drive.
For a distinctly non-seedy music experience, try the kids-friendly classical and world music concerts at this community-based not-for-profit music school.
Built in 1926 with an interior that is meant to recreate a Spanish palace courtyard, the Aragon cost more than two million dollars at the time, and the well-preserved interior still has the otherworldly brilliance. It shifted from big-band sensation to prizefight arena and swinging mod disco, but it's been in good hands for more than thirty years now, as promoters for Latin dances and rock shows split nights of the week.
Jazz and lots of it at this Uptown landmark, famously an old hangout of Al Capone (who's not, though, around as much as he used to be). Go on a Sunday evening for the weekly poetry slam. There are a few excellent resident jazz ensembles.
Not a tourist sight, necessarily, but a center for the local South-east Asian community, young and old. Ten languages (besides English) are spoken by the staff. Volunteer opportunities like English teaching and elderly care abound.
From 1907-17, Hollywood was in Uptown. A dizzy list of silent movie giants shot films here, Charlie Chaplin and local girl Gloria Swanson among them, and the city's awful winters played a part in shifting production to California for part of the year. When Chaplin left, the studio collapsed, and California started seeming more attractive year-round. The building is now a protected landmark, and houses the bi-lingual http://www.staugustine.edu/ St Augustine College]. No tours are available, but check out the grand name above the doorway.