© City of Chicago / GRC

From awe-inspiring museums, amazing architecture, and a vibrant waterfront to great music, good food on nearly every corner, and legendary sports teams and venues (hello, Wrigley Field), summer in Chicago is a glorious place to be. With plenty of direct flights to Chi-town from Charlotte, you can hop on a plane after work on a Friday, experience the Windy City in a day and a half, and be back in time for your Monday-morning meeting.


Hotel Blake (500 S. Dearborn St., on historic Printer’s Row/South Loop is centrally located—meaning if you walk a few blocks, you’re staring up at Willis (formerly Sears) Tower or strolling down swanky Michigan Avenue. The Blake breaks the stereotypes of hipster boutique hotels with large rooms and even larger bathrooms. (Tip: don’t hesitate to ask for an upgrade. The staff is quite accomodating.) From $129 per night.


It’s practically illegal to visit Chicago and not eat deep-dish pizza. Try Pizzeria Due, part of the Pizzeria Uno family (619 N. Wabash Ave.,, purveyors of the original deep dish. Want to dine like a local? After taking in a Cubs game at Wrigley Field, hit up Lou Malnati’s Pizzeria (958 W. Wrightwood Ave., (about ten minutes from the park). Order the sausage lover’s pie — a massive 11.5-inch patty sits atop a 12-inch pie. For a wine-and-cheese sampler (pick from more than thirty-five varieties), stop by Eno at the InterContinental (505 N. Michigan Ave.,, a good spot to chill after shopping or a night on the town.


Plan on taking the Chicago Architecture Foundation’s boat tour (224 S. Michigan Ave.,, during which a foundation volunteer narrates the cruise and gives you a sense of the city’s history. Later, head to the Art institute of Chicago (37 S. Wabash Ave.,, both a school and a world-class museum, practically pulsating with creativity. Don’t miss the Modern Wing, with the iconic American Gothic by Grant Wood and Nighthawks by Edward Hopper.


The big (and breathtaking) must-see is The Ledge at the Skydeck at Willis Tower, formerly the Sears Tower (233 S. Wacker Dr., A series of glass boxes that extend a little more than four feet from the 103rd floor, The Ledge allows you to see the city in its 180-degree beauty. Use a $30 Fast Pass to skip the long lines. Later, catch a show by the famous Steppenwolf Theatre Company (1650 N. Halstead St., More of a comedy lover? Swing by Upright Citizens Brigade (307 W. 26th St., –where SNL comedian Amy Poehler got her start.

Getting There

There are several daily nonstop flights from Charlotte-Douglas International Airport to Chicago O’Hare. Expect the flight to take a little more than two hours.

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