Billed as "one of the greatest outdoor urban bazaars ever," the historical Maxwell Street Market is the best way to get a true sense of the Windy City. Once a bustling 19th-century Jewish market, Maxwell Street has morphed into a cultural meeting place where all races and nationalities gather for the music, merchandise and cheap eats. Widely famous for impromptu jam sessions, this flea "turns the beat around" with a mix of jazz, blues and Latino sounds filtering through the stalls. Today’s flavor is distinctly Mexican, especially with the many roaming food carts. There’s also plenty to sift through, from tires, autoparts, and old televisions to art and some antiques.

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