· Sticking to the Michigan Ave and Loop areas
While the Loop is a lovely place to hang—strolling Millennium Park and Michigan Avenue are worth the trip alone—it’s the neighborhoods that give the city its character. Head to Chinatown for dim sum, Wicker Park to see work by local designers and artists, Lincoln Park to knock a few back at some frat-tastic bars and Wrigleyville to witness the indigenous Cubbies in their natural North Side habitat (more on that later). The truly intrepid tourists can head to the north side's Devon Avenue for the best Indian food this side of Mumbai and some saris to match.
· Heading to the Theater District to see a play.
Now, we’re all for some good theater, and you’ll find some fine shows at stalwarts like the Goodman. But really, you can see Jersey Boys in any major city. Check out the homegrown talent at independent venues like Strawdog Theatre Company, The House Theatre of Chicago, Red Moon, and the really avant-garde Trapdoor Theatre.
· Not booking event tickets ahead of time.
People who come to Chicago are usually in search of two kinds of tickets: Cubs tickets and Oprah tickets. Chicagoans don’t joke about their team allegiances, so even when the beloved Cubbies are having the worst season ever, the stadium sells out. Order your tix in advance on the Cubs’ website. Make like a local and sit with the bleacher bums (the superfans) in the cheap bleachers—and use the cash saved for the fan fave Old Style beer.
Oprah tickets however go faster than her wallet-busting “Favorite Things” show. After years of frustrating fans, the show is revamping its ticket system; instead of getting them on the always-jammed reservation phone line, tickets will be up for grabs on Oprah’s website so long as you are a site member.
· Ordering a hot dog with ketchup.
If you’re caught ordering a dog with just the red stuff, natives will shun you and especially so if you are at Wiener’s Circle at 2622 N. Clark Street. It's one of the best dog dives in town and the temperamental cooks will curse you out. (We’re not kidding on that last part.) Be sure to get your dog with the works (mustard, relish, onions, tomato, a pickle, sport peppers and celery salt) and save the ketchup for your fries.