1. Shop the Mile: Rodeo Drive in LA has nothing on the Magnificent Mile. That’s a fact. Visitors to the city hit the Mile in droves, but lots of locals do too. Water Tower Place on N. Michigan offers seven stories of fantastic shops, and not all of them are over-priced tourist traps. Chicago Place has eight floors of stores like Saks Fifth Avenue, Ann Taylor and Chiaroscuro. Other faves are the American Girl Place, Bloomingdale’s, Coach, Gucci, Carson Pirie Scott and the original Marshall Field’s.
2. Celebrate: The city has a spectacular calendar of events with dozens of great festivals. Local favorites include the Chicago Blues Festival, the Gospel Music Festival and the Printers Row Book Fair in June, Taste of Chicago in June/July, the Country Music Festival in July, the Chicago Jazz Festival in August/September, the Celtic Festival in September, the International Film Festival in October and the Holiday Sports Festival in December.
3. Take yourself out to the ballgame at Wrigley Field: Seeing a day game at this famous ballpark is a “must” for baseball aficionados. The Wrigley neighborhood has a lot of choice bars and eateries for after the game. The White Sox play on the South Side. The Bears play football and the Fire play soccer at Soldier Field. The Bulls and Blackhawks are your winter options at the United Center.
4. Head from the Cubs to the clubs: Chicago has many great bars and clubs where you can hear local music, sample Chi-Town drink favorites and hob nob with the natives. Jazz bars, cigar bars, sports bars, swanky cocktail lounges and all your favorite drinking establishment genres are right here. Just a few you might want to start with include Red Ivy 1914, Buddy Guy’s Legends, Green Mill Cocktail Lounge, the Pump Room, and Scofflaw.
5. Sample the classic sounds: Classic music means many different things, and Chicago has them all. The Chicago Symphony Orchestra is one of the best in the world. The Sinfonietta and the Renovo String Orchestra offer classic diversity. Chicago is also renowned for American classic genres including soul, jazz, gospel, rock, Dixieland and hip-hop. You’ll find venues all over town to suit your taste in classic music.
6. Browse books in the Loop: There are more than 20 bookstores in the Loop featuring everything from new releases to out-of-print treasures. Look for the Greater Loop Book District pamphlet available at the airport and around town to guide you.
7. Stroll Navy Pier: This is a great place to spend an afternoon overlooking Lake Michigan. The 50-acre Pier offers parks, gardens, lots of cool shops, boats and ships of every kind and a pleasing array of restaurants to suit every taste.
8. Take art to heart: The Art Institute of Chicago has a world-class reputation. Locals get yearly passes that allow them to study the permanent collection at their leisure and catch all the short-run exhibits. No matter when you visit, you’ll find a rich blend of artwork representing every period and style. Don’t overlook other galleries such as the Mexican Fine Arts Center and galleries featuring works from Polish, Swedish, Japanese, Korean and Chinese artists.
9. Treat your taste buds to ethnic dishes: Yes, the locals do indulge in Chicago deep dish pizza. But there’s a much wider gastronomic smorgasbord in the Windy City. Ethnic enclaves around town offer authentic food from around the world. For world-class food, scout Mexican villages along 18th Street, the Puerto Rican Paseo Boricua in Humboldt Park, Greektown on South Halsted, Little Italy on Taylor Street, Indian and Pakistani enclaves along Devon Avenue, Vietnamese restaurants on Argyle and Chinatown and Polish Patches and Little Seoul along Lawrence Avenue.
10. Get tix to the theater: The theatre community is thriving. Outstanding venues include Goodman Theater, Victory Gardens Theater, the Ford Center for the Performing Arts, Broadway Playhouse at Water Place Tower and the Gateway Theater. More than 50 theaters put on productions ranging from the serious to the sublime to the satirical.