Chicago

The Art Institute of Chicago

Attractions

★★★★★

Nighthawks, American Gothic, and a Seurat you know from Ferris Bueller. Enter between the bronze lions on Michigan Avenue.

Millennium Park

Outdoors

★★★★★

Home of the Bean and free summer concerts at the Pritzker Pavilion. The skyline reflection photo is mandatory.

Au Cheval

Food

★★★★★

The diner burger regularly called America’s best. Put your name in, then go for a drink — the wait is legendary and deserved.

Intelligentsia Millennium Park

Coffee

★★★★★

The flagship of the roaster that helped invent third-wave coffee, steps from the park. The Black Cat espresso is the classic.

Bang Bang Pie & Biscuits

Dessert

★★★★★

Logan Square’s pie shop with a backyard garden. Key lime and a biscuit with honey butter make a respectable lunch.

The Violet Hour

Drinks

★★★★★

Behind an unmarked, ever-repainted facade in Wicker Park. High-backed chairs, candlelight, and cocktails that started the city’s renaissance.

The Magnificent Mile

Shopping

★★★★★

Thirteen blocks of flagships on Michigan Avenue, bookended by the Wrigley Building and the old Water Tower.