Why I Fell Back in Love With Chicago After Years Away in New York

I touched down in Chicago during a freak February warm spell that stretched five days—three longer than my weather app predicted. I'd packed cashmere, but the thermometer hit the 50s and 60s, breaking a single-day record. As a lover of crisp winter air, I was let down. Locals, however, flocked to Lake Michigan, biking and strolling the 18.5 miles of uninterrupted shoreline from South Shore to Edgewater. I swapped my sweaters for cotton and joined them.

There's nothing quite like walking that lakefront in my hometown. I'm embarrassed to say I only recently learned most of it is man-made—ash from the Great Chicago Fire was used as landfill in places. It's all thanks to architect Daniel Burnham's 1909 vision that the waterfront would stay "forever open, clear, and free of any buildings." And it does. That contrast hit me hard when I later moved to West Chelsea, New York, where the Hudson River, just two blocks away, was considered dangerous and off-limits. Today, of course, it's a completely different story.

I've now lived in New York longer than anywhere else and call it home. But I return to Chicago several times a year and feel proud the city is getting its due. A native son (a White Sox fan, I'll admit) was elected pope last year, The Bear keeps generating buzz, and the Obama Presidential Center opened in June in a park designed by Frederick Law Olmsted for the 1893 World's Fair. Chicago has all the makings of a first city: an iconic skyline, world-class museums, a ridiculous food scene, and 77 distinct neighborhoods shaped by waves of migration.

But where New York runs on ambition and Los Angeles on dreams, Chicago runs on opportunity. As Claire Warner of Volume Gallery told me, "You can still create something with an idea here." She and cofounder Sam Vinz noted that Chicago lets you incubate in ways New York or LA don't. For me, it's America's quietly confident city—industrious without being frantic, proud without being performative, cosmopolitan without forgetting its manners. Every shop I visited greeted me warmly. In a country that often shouts for attention, Chicago simply gets on with being great. I don't see myself leaving New York, but every time I return, I find myself browsing real estate listings.