It’s the first week of September, most of the kids are back at school and no one can believe how fast the summer has flown by. But it’s not over yet. Set off on one of four great trips from Chicago, ranging from road trips to a deal-busting direct flight and perfect for an end-of-summer hurrah.
1.5 hours by car
Why Go Now: From September 3 to 7, Harley riders flood the city for the Milwaukee Rally & Custom Bike Show at the Harley-Davidson Museum. Not a Harley rider? You’ll still be in awe of the high-style eye candy both at the museum and rumbling around town.
While There: See art of a different kind at the waterfront Milwaukee Art Museum. It is largely closed for renovation, but there’s still one big redeeming exhibit: “Van Gogh to Pollack: Modern Rebels,” which ends September 20 and includes works by Frida Kahlo and Roy Lichtenstein. If you have the kids, walk next door to Discovery World, a sprawling museum packed with interactive science and technology exhibits (compete with a robot in tic-tac-toe!), and one of the best aquariums spotlighting the Great Lakes (touch a giant sturgeon!). In between, grab a bite in the Third Ward at the buzzy Milwaukee Public Market.
Stay: At the loft-style Iron Horse (from $179), a boutique homage to Americana and hog riders, less than a five-minute ride from the Harley-Davidson Museum.
2.5 hours by car
Why Go Now: Chicago ex-pat chefs Dan Fox and Dan Bonnano of Pig in a Fur Coat host a Mangalitza pig dinner at Fox’s pub-vibbed Heritage Tavern, alongside Barbara Meyer, a Mangalitza breeder from the Netherlands and author of a new book on the breed. Fox, who worked at Everest and Spring before moving to Madison, raises his own Magalitzas at a nearby farm. “The Mangalitza has unbelievable fat and meat quality,” says Fox. “It cannot be compared to any other pig.” The dinner happens September 9 at 5:30 p.m. ($95).
While There: On Saturday, hit the capital grounds for the world’s largest producer’s only farmer’s market in the U.S., while it’s still outside. Climb the stairs to the capital building, too, for a look at its soaring ceilings.
Stay: At the college-cool Graduate Madison (from $159), a new brand from Chicago’s own AJ Capital. Nab a seat on the new rooftop for some of the best Parisian-style views of the capital.
5 hours by train
Why Go Now: In early August, Iowa Pacific took over the Hoosier State train run by Amtrak between Chicago and Indy, classing up the once underwhelming experience with a domed parlor car, full meals served on white tablecloths with flowers, a full bar, Wifi, and a nicely upgraded ride. The Hoosier State train runs four days a week with tickets from $24.
While There: Head to Indy’s Monument Circle for Spark, a huge social art experiment that’s about creating dynamic places. They call it “placemaking,” which pans out to interactive art making, story sharing and listening booths, ping pong, pop up parks, and guided bike tours. Spark runs daily from 11 a.m. to 8 p.m. through October 16.
Stay: Crowne Plaza at Historic Union Station keeps the train theme alive; sleep in one of its 26 original Pullman train cars, still on their original tracks (from $119).
Meatpacking District, New York
2 hours by plane
Why Go Now: Take advantage of amazing fares from O’Hare to New York’s LaGuardia Airport—as low as $97 on Spirit Airlines—to get to the new Whitney Museum of American Art for the one-time-only “America is Hard to See.” Drawn entirely from the museum’s outstanding collection, the show depicts moments in American history as chapters across its eight floors. Don’t miss the outside gallery and Mary Heilmann’s exuberant “Sunset.”
While There: If you haven’t yet seen the 9/11 Memorial and Museum, which opened in May of 2014 and will necessarily upend you, there’s no more timely month than September. Before you go, download the free museum walking tour apps narrated by Robert DeNiro.
Stay: Plant yourself in the Meatpacking District at the Gansevoort Meatpacking NYC hotel (from $275), a five-minute walk from the Whitney, High Line, and Chelsea Market.