Map out a world-class donut crawl
Chicagoans don’t have a problem with a little extra Midwestern girth, especially following another grueling winter trapped in cold and darkness. If you want to truly experience the city like the locals do, you should also eat like they do. Which means eating donuts. Lots of them. Try creating your own crawl of any of the best donuts in Chicago or sit back and leave it to the experts. Either way, you can’t go wrong with a visit to Do-Rite, one of the best in the nation.
...Or take a boozy boat tour
On a nice summer day in Chicago, there’s no better way to see the city than by boat (just ask Vince Vaughn in The Break-Up). But not all booze cruises are created equal. From laid-back architecture tours to raucous floating tiki bars (with waterslides) that you can rent out with 70 of your idiot friends, Chicago knows that this is the best way to enjoy its picturesque lake and river views.
Go on a culinary expedition at a local food hall like Revival or Eataly
While food halls are all the rage these days, Chicago got in on the scene early and now offers a number of massive urban temples teeming with culinary delights. The 24,000-square-foot Revival Food Hall, housed in a historic 1907 building downtown, offers everything from tacos and ramen, to BBQ and gelato. Meanwhile, more specialized food halls include Eataly (famous for its high-end Italian cuisine), Latinicity, and Chicago French Market.
Stuff your face in a train car at Silver Palm
Have you or your friends ever eaten dinner in a train car? If not, a trip to Silver Palm should definitely be on your list. The legendary neighborhood hang is known for its massive 3 Little Piggy sandwich piled high with ham, pork, bacon, egg, and an onion ring, but the fried chicken and ribs are no slouches either. Whatever you eat, there’s no denying the experience is enhanced by eating it in a train car.
Instead of dragging your out-of-town guests to some stupid skyscraper tourist trap, let them enjoy the jaw-dropping views while hanging out with real-life actual Chicagoans at one of the many excellent rooftop bars that dominate the city skyline. Drumbar in Streeterviller, the J. Parker in Lincoln Park, and Cindy's in the Loop are all fine options. And several of our rooftop bars are open year-round, so you have no excuse not to pay at least one of them a visit.