Take it from a native son: Chicago is at its best as summer moves toward fall, when the hot, humid days of August are already forgotten and locals can remain in denial about wi-n-ter’s inevitable onslaught for a while longer. This is the season for catching a Cubs game (the team is actually showing signs of life) or roaming the revived Chicago River, reinvigorated neighborhoods, and innovative parks that carry on the City Beautiful vision of 19th-century urban planner Daniel Burnham. They’re a reminder of how a restless Chicago forever looks ahead, even as it venerates a past of steel mills, stockyards, and the birth of the blues.
Old-school Chicagoans might scoff at the notion of $3 doughnuts—that is, until they bite into the praline, white chocolate, and lavender-honey confection at the La Salle Street outlet of downtown’s Glazed and Infused. You can eat it along the ever-expanding Chicago Riverwalk, which leads past kayaking concessions and waterfront plazas, to reach Lake Michigan. Thanks to Burnham’s transformative 1909 plan, the Third Coast’s first coast remains virtually free of development. Grab a pair of wheels from Divvy, Chicago’s bike-share service, then ride a stretch of the 18-mile Lakefront Trail as it connects parks, beaches, and such cultural attractions as Hyde Park’s grand old Museum of Science and Industry. Right off the trail near downtown, a serpentine brushed stainless steel bridge designed by Frank Gehry connects the inventive playscapes of the newly unveiled Maggie Daley Park to Millennium Park and Anish Kapoor’s shimmering Cloud Gate sculpture, better known as “The Bean.” Don’t miss Lurie Gardens, a tapestry of native plants that creates the illusion of the city’s skyscrapers rising from a prairie.
Across Michigan Avenue the Chicago Athletic Association Hotel ($269-$1,200) just debuted in a renovated 1893 Venetian Gothic building, where you can linger over coffee in the lobby and admire the vintage details. On the rooftop, 13 floors above a street-front Shake Shack and the second level’s clubby Cherry Circle Room, Cindy’s mixes lake views, picnic tables, and lavish seafood platters. The hotel is two blocks from the Art Institute of Chicago, notable for Renzo Piano’s light-washed modern wing, but it’s also within strolling distance of the Virgin Hotels Chicago ($157-$350), which occupies a 1928 bank building and marks the Branson brand’s first foray into lodging. Above a screechy bend in the “L” tracks and a block from the river and Michigan Avenue, the hotel’s rooms have a playful, contemporary feel, sporting separate dressing and sleeping areas. Inevitably you’ll head to the 26th-floor lounge, Cerise, for drinks and izakaya small plates, but you’ll also want to take a quick walk to Eataly, an emporium that overwhelms with 63,000 square feet of wines, cheeses, breads, and olive oils, along with several restaurants. Chicago is compact, so it’s simple to ride the Red Line L from Grand Avenue to Wrigley Field, which, in spite of a major modernization campaign, remains the country’s most beautiful ballpark. Or take the Blue Line to The 606. Newly opened, the 2.7-mile-long park was created atop a defunct ele-vated train line that connects the happening Wicker Park and Logan Square neighborhoods. About a mile north of the 606, Longman & Eagle, a Michelin-starred rustic hang that helped spark Logan Square’s revival, draws crowds with such brunch offerings as a wild boar sloppy joe.
If you do just one Chicago Architecture Foundation tour, try the twilight journey up the Chicago River to see the city’s most famous skyscrapers, from 1920s landmarks to more recent classics, like Adrian Smith’s 92-story Trump Tower. Over in the West Loop’s Fulton-Randolph Market District, a meatpacking and produce area that has evolved into a dining destination, James Beard Foundation winner Stephanie Izard’s adventurous Girl & the Goat lives up to its name with such starters as goat empanadas and carpaccio. At bellyQ, Charlie Trotter alum Bill Kim serves Korean barbecue, as well as tuna with coconut grits, in an old pickle factory. After dinner, cab it north 20 minutes to the Green Mill, one of the city’s most atmospheric jazz rooms and a favorite of Al Capone’s. In case you’re peckish at closing time, Wiener Circle (ten minutes away) stays open until 5 a.m., the port of last call for Chicago nighthawks hungry for classic char dogs.
Stretching along 15 miles of Lake Michigan, Indiana Dunes National Lakeshore has its very own Mount Baldy—all 126 feet of it—as well as trails through oak savannah, beech-maple forests, and sand prairie habitat. Views from the beach offer a unique perspective on the Chicago skyline 50 miles away. It’s 80 minutes via the South Shore Line commuter rail.
The Blue Line L rapid transit train takes about 40 minutes to reach downtown from O’Hare International Airport. The Orange Line L from Midway Airport takes 20 to 25 minutes.
Summer festivals along the lakefront attract crowds, despite the humidity. But late summer into autumn is prime, with warm days and changing leaves by the middle of October.
In September, one of Chicago’s best weather months, the average high is 76 degrees, with progressively cooler conditions as fall advances. Rain is always a possibility.