Chicago beaches are one of the best things about Chicago summer, yours to enjoy at less crowded but still centrally located spots like the criminally underrated Ohio Street Beach. With its on-site Caffe Oliva slinging drinks and fish tacos with the downtown buildings to one side and the equally underrated Milton Lee Olive Park on the other, there’s not a bad view to be had.
Devour an Italian beef sandwich
Little Italy/University Village
No doubt Johnnie's Beef in suburban Elmwood Park certainly makes a damn fine Italian beef sandwich. But if you’re in the city with out-of-towners and want to show them a unique slice of life, a trip to Chicago’s Little Italy/University Village neighborhood should be high on your agenda. Pair your beef sandwich from the historic neighborhood Al’s Beef stand with an Italian ice from Mario’s Italian Ice to give your visitors a a damn fine taste of old-school Chicago.
Perhaps the number one touristy activity that locals will be most secretly psyched to participate in is a cruise on the Chicago River. Yes, the boozy variety is an option, but as your fourth-grade teacher once said, you’re here so you might as well learn something. The Chicago Architecture Center runs an excellent 90-minute river cruise aboard Chicago’s First Lady (with a bar on the boat offering up a heady Chicago Mule, so there ya go). CAC volunteers talk you through the architectural styles, historic landmarks, and new developments that mix and mash along Chicago’s gorgeous riverfront, like the very tremendous Trump Tower, those towers from the Wilco album cover, and the Sears, er, the Willis Tower.
Do deep dish -- the right way
So yeah, most out-of-towners will inevitably inquire about deep dish pizza at some point in the conversation. While you can tell them that that Chicagoans by far prefer thin-crust pizza and that the tourist-packed deep dish joints downtown are akin to Michael Scott’s visit to the Times Square Sbarro, there are still neighborhood joints doing deep dish the right way. Pequod’s in Lincoln Park is a fine example within city limits, with Burt’s Place out in suburban Grove is more than worthy of a little road trip.
Understand why the Chicago-style hot dog is the only style
Complete the holy trinity of Chicago food by taking down a Chicago-style hot dog at a local institution like retro drive-in Superdawg, which hasn’t changed much since opening in 1948. Or if you’re particularly hungry, a trip to The Weiner's Circle may be in the offing. Just be prepared; it's one of Chicago's most foul-mouthed culinary experiences.
It's been a last meal request. It's been a hangover cure. President Obama dined there. As did President Clinton. As did just about every politician who ever set foot in Chicago. And so should you. Power lunch on a Reuben or beef pastrami in this legendary cafeteria-style diner where business (and the occasional shady deal, of course) gets done in Chicago.