A lot has changed in Chicago—but not everything. Many of the tried-and-trues are as worthy as ever.
If the newer architectural tours are too froufrou for you, Wendella offers this: the timeless two-hour sunset cruise. You'll take in all the sights (Magnificent Mile, Chicago Harbor Lock) as the sun goes down, and then pull into Monroe Harbor to watch the Buckingham Fountain water-and-light show (wendellaboats.com, $26).
"Cheezborger! Cheezborger! No Pepsi, Coke!" Even if the 1970s John Belushi and Dan Aykroyd parody of the Billy Goat Tavern doesn't ring a bell, you'll be entertained while ordering your double cheeseburger at this dingy Greek burger joint (430 N. Michigan Ave., Lower Level, billygoattavern.com, double cheeseburger $4.75).
Little-known fact: Many of Chicago's most famous sights date back to '95: 1895, that is. If you've read Erik Larson's The Devil in the White City, you'll want to visit landmarks from the 1893 World's Fair, including the Art Institute (artic.edu, $18) and the Museum of Science and Industry (msichicago.org, $15).
Yes, Oak Park, Ill., which is a quick El-train ride from the Loop, is both Hemingway's birthplace and the center of Frank Lloyd Wright's Prairie School movement. Be sure to start your cultural tour there on a summer Saturday, with a trip to the Oak Park Farmers' Market Donut Stand (460 Lake St., oak-park.us, May 21–Oct.).
The Cultural Events
In 1995, Lollapalooza was an alt-rock music festival that toured nationwide. Today, the event calls Chicago its sole home (Aug. 6–8). Which isn't surprising: The city has long been a great festival town, with everything from the Chicago Blues Festival (July 11–13) to the Taste of Chicago (June 25–July 4).