The Green Line
Chicago's elevated trains are one of the city's most recognizable and entertaining features: Their booming rumbles tipped off Tommy Lee Jones to Harrison Ford's whereabouts in The Fugitive, and driving directly underneath them is like enjoying your own mini-earthquake. The Green Line never goes underground, and the 30-minute path from downtown to the end of the line in Forest Park is a rolling tour of the industrial center that Chicago once was. You'll be able to look down on some of the fire-touched abandoned buildings, junk car lots, graffiti and indeed some thriving industry, such as car repair shops and tuckpointing outposts. There are even a couple parks along the way, including Garfield Park, which has an impressive conservatory.
When you get off at the end the line at Harlem, go out the westernmost exit toward Forest Park; turn right on Circle Avenue and walk a block to Circle Bowling Lanes. The alley opened in the mid-1940s and not too much has changed since — you'll have to keep score by hand. Afterward, walk another block down for the burgers, cheese curds and beer at Goldyburgers.