Most tourists in Chicago can be spotted from a mile away, and most travelers are OK with that. It works in Chicago, as, generally, the locals are happy to help out the lost visitor. Before you go, you'll want to get off the beaten path, do a little research on the CTA (Chicago Transit Authority) trip planner and get lost in a brand-new experience.
As soon as you walk into the front entrance to Navy Pier -- one of Chicago's most popular tourist attractions -- and see that one of its anchor restaurants is the Bubba Gump Shrimp Company chain, it's obvious from the start that Navy Pier has nothing to do with Chicago and exists for one reason only: to suck money out of tourists' wallets. Most locals won't go to Navy Pier on a bet. There is one good reason to visit the pier, however, and that's to board an Odyssey dinner cruise on Lake Michigan -- the lights and views can soften even the most hard-hearted native.
While Chicago's grid system of streets make it easy to navigate around the city by car, the traffic does not. So get out of the comfort zone of your rental car and take Chicago public transportation instead. It's easy to take public transportation to almost all major Chicago attractions, with some buses providing almost door-to-door service, and the CTA provides 1-, 3-, and 7-day unlimited ride passes making it even more convenient. You can also figure out your exact route ahead of time with the Regional Transit Authority trip planner. And trust me -- riding in some Chicago cabs is way scarier and intimidating than taking the subway.
The historic brick and ivy at Chicago's Wrigley Field is too alluring to say "skip the Cubs game" to a die-hard baseball fan. You're encouraged to also head down to 35th street to check out the Chicago White Sox. The only Chicago team to win a World Series in the last 100 years, the White Sox play in U.S. Cellular Field, built for the team in 1991 (call it "new Comisky" to really sound local -- Comisky Park being the Sox's former home). It's located in Bridgeport, which is adjacent to Chinatown.
Eat Some Real Chicago Pizza
While Chicago-style deep dish pizza might be worth experiencing once to say you've tried it, if you want to get more of a sense of what most Chicagoans are ordering on Friday nights go somewhere you can try Chicago's take on the thin crust pizza. Its thin crust also has a regional flair of its own and tends to have a thinner, crispier crust than its New York counterpart. A couple of good options are Pat's Pizza in Chicago's Lincoln Park neighborhood, or if you're traveling with people that simply have to have deep dish, head to Lou Malnati's where you can get the best of both worlds.
Head South of Madison Street
Madison Street in Chicago is the official north/south dividing line of the city, and visitors tend to stay mostly on the northern portion of that divide. But by doing so, you'll be missing out on a lot of culture on the city's South Side such as the Hispanic Pilsen neighborhood, and Chicago's Chinatown. Chicago's Hyde Park neighborhood is also on the South Side, which is home to University of Chicago, the Museum of Science and Industry, and is the Chicago home base for someone you may have heard of, President Barack Obama.
Head a little further south and encounter Stony Island Arts Bank, which has been completely restored and now holds long-forgotten treasures, films and artwork from up-and-coming artists.
Watch Where You're Going on Michigan Avenue
With Michigan Avenue's array of hotels, shopping, and businesses, it has the most congested pedestrian traffic in Chicago. And one of the biggest complaints you hear from locals is that out-of-towners are completely incognizant while traversing the Magnificent Mile. So this one's easy to look like you're just out on your lunch hour than visiting from out of town: don't walk abreast if you're in a group, stay to your right and simply be aware of other people around you.
Find an Alternate Skyscraper View
Sure, you can go to the Hancock Observatory or Willis Tower to take a look at Chicago from up high, but why not get a little more creative? A favorite place to show off the city and lake is Cite Restaurant, on the 70th floor of Lake Point Tower across from Navy Pier. While not quite as high, the views are still stunning and you can get an appetizer and cocktail with the money you would have spent on an observatory ticket.
Visit a Lesser-Known Museum
Places like the Art Institute and the Field Museum are world-class museums, but I would also encourage you to visit some other smaller museums off the beaten path that not only offer unique exhibits but also, quite frankly, could more use your support. A few worth highlighting are the Intuit Center for Intuitive and Outsider Art just west of downtown, the DuSable Museum of African-American History in Chicago's Hyde Park and the National Vietnam Veterans Art Museum.