Choose close-together activities that will stretch your dollar. We dropped $47 for bike rentals, but that gave us a cheap, fun way to zip along the lakeshore, checking the 31st Street Beach, Navy Pier and the Lincoln Park Zoo (all free!) off our list. And, since the bikes came with locks, we could stop and sightsee -- or join families wading in Millennium Park's Crown Fountain (left).
Go where the crowds don't. Pre-trip research clued me in to the little-known Bridgehouse Museum, where, for just $3 apiece, we saw the massive gears that lift the Michigan Avenue bridge, and we learned all about the Chicago River. Visiting that hidden gem freed up the last of our $500 for two not-so-cheap rides up the Hancock Tower for Juan's first bird's-eye view of Chicago.
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