If you’ve been on a walk through Chicago, you’ve probably found time to breeze along State Street or Michigan Avenue. Fine streets both, but why not try going in a different direction?

North Alta Vista Terrace

Located just a block or two north of Wrigley Field, this quiet residential block appears to have been lifted out of Mayfair. Designed to mimic a clutch of London row houses, it’s also Chicago’s first historic district.

West Burton Place

Just off the bustle of Wells Street in Old Town, this one-block-long enclave features several homes reinvented as a mini-artist’s colony in the 1920s. Peek into the courtyard to see a range of decorative tiles and repurposed architectural fragments.

North State Parkway

From Queen Anne mansions to Art Moderne apartment complexes, this stretch of State Parkway on the Gold Coast is an architectural delight. Along the way, you’ll see Hugh Hefner’s former Playboy mansion and the official residence of the Roman Catholic archbishop of Chicago. It’s hard to miss; it’s got 19 chimneys.

East 58th Street

Slipping onto 58th Street in the center of Hyde Park will guide you by a raft of gray Collegiate Gothic glories on the University of Chicago campus. Along the way you can stop by the Divinity School Cafe (it’s appropriately called “Grounds of Being”) and look over the galleries containing archaeological wonders at the Oriental Institute.

West Wacker Drive

On this stretch of Wacker Drive, you’ll have stunning views of the Art Deco Merchandise Mart to the north while walking in the shadow of modern masterpieces to the south. Be sure to check out the curved glass façade of 333 Wacker Drive and 77 West Wacker Drive, which is topped off with a Roman pediment.

South Dearborn

In this canyon of architectural wonders in the Loop, walkers can stop by the Monadnock Building for a latte at Intelligentsia Cafe and marvel at this early skyscraper. This stretch of Dearborn also includes the Marquette Building, which has elaborate relief sculptures depicting the life of Jacques Marquette, noted 17th-century explorer and Jesuit priest.

North Damen Ave

To walk the blocks of North Damen Avenue between North Avenue and the Bloomingdale Trail (a.k.a. the 606) is to be tempted by culinary delights at just about every step. You can pick up picnic supplies on your walk at the Goddess and Grocer and stop by Mindy’s Hot Chocolate, for, well, you guessed it. Step on up to the 606 to explore this new and wonderful linear park through the heart of the city.

West 18th St

Walking down 18th Street presents the casual stroller with a series of compelling murals depicting the Pilsen community’s history, along with the opportunity to stop by and take in a show at the recently renovated Thalia Hall. Don’t forget to look up at the spire of St. Procopius Catholic Church, which is a fantastic reminder of the area’s Czech past.

East Lake Shore Drive Historic District

This stunning long block along Lake Michigan offers up a heavenly troika of gorgeous apartment buildings by the noted architectural firm of Marshall & Fox. Primarily from the roaring 1920s, the structures here provide a riot of detail, including gorgeous Second Empire-style mansard roofs. Stroll on over to the Drake Hotel for their afternoon tea service after you’re done for petit fours and oolong.

West Armitage

Hopping off the CTA’s Armitage stop, you can wander along West Armitage to explore the vast range of architectural styles (including Italianate) represented in the commercial structures that line these blocks. As you walk around this late 19th-century landscape, you’d do well to stop by Glazed and Infused, a local luxe donut emporium.

—Max Grinnell

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