There's something infinitely cool about hitting the beach while the skyline of a major American metropolis towers above you. If you happen to visit Chicago in the warmer months, do what the residents do and stake out your own piece of the 26 miles of sandy beaches along Lake Michigan. Virtually all the coastline is open to the public (there are very few private beaches). Oak Street and North Avenue beaches are where the more fashionable crowd hangs out; Rogers Park and Rainbow Beach are a bit more laid back. Bring your trunks, towel and one of the city's famous hot dogs.