2. Take Public Transportation
Chicago Subway Entrance. Photo by Tim Boyle/Getty Images
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 more scary and intimidating than taking the subway. More »
3. Go to a White Sox Game
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4. 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 sense of what most Chicagoans are ordering on Friday nights go somewhere you can try Chicago's take on the thin crust pizza. Our 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.
5. 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, U.S. President Barack Obama.
6. 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 I 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.
7. Find an Alternate Skyscraper View
Sure, you can go to the Hancock Observatory or the Sears Tower Skydeck to take a look at Chicago from up high, but why not get a little more creative? My 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.
8. Visit a Lesser-Known Museum