Just the name of the street --- Astor --- conveys an image of prestige and power. Indeed, Astor St. WAS the home of many of turn-of-the-century Chicago’s wealthiest families, and some of their mansions still stand. Strolling past them is a great way of unwinding after a day of power shopping on Michigan Ave.
The southernmost block of Astor St. now contains many high-rise condos and isn’t as attractive as it used to be. So, let’s start our walking tour at Division St. and North State Parkway and admire a mansion with a different sort of notoriety: The conjoined buildings at 1336-1340 N. State are the former Playboy Mansion --- the late Hiugh Heffner’s infamous "Bunny Hutch".
Continue north to Schiller and turn toward the lake. At the intersection of Schiller and Astor is the Charnley House, built in 1892 by the firm of Louis Sullivan, an employer and mentor of Frank Lloyd Wright. Walk north along Astor and imagine yourself living in one of the magnificent old greystones you’ll pass. The Patterson-McCormick Mansion, 1500 Astor, is an even statelier example of Prairie School design. (The "McCormick" was Cyrus R., who reaped a fortune from inventing the first successful mechanical grain harvester.) This isn’t a Wright building, but there are several of his works --- including his own home --- in nearby Oak Park.
Admire the parkway gardens --- gardening is a competitive sport here --- as you continue north to The Cardinal’s Residence. This angular brick mansion, with nearly a score of chimneys, has been the official residence of Chicago’s Roman Catholic archbishops for a century and a half. In the late 1970s, I watched the then-Pope address congregants from its balcony.
If it’s a pleasant day, you can enjoy magnicient views of Navy Pier, the north end of the Magnificent Mile, and the Chicago skylne by walking a block east to the lake, through a pedestrian underpass beneath Outer Lake Shore Drive, and as far out as you care to venture onto the breakwater at North Ave. Beach.
The quirky Museum of Surgical Science is in the 1500 block of Inner Lake Shore drive, just south of the pedestrian underpass. It normally charges admission to its collection of centuries-old medical tools and memorabilia, but is free on Tuesdays.
You can walk back along the lakefront seawall to Michigan Ave. or swing back west through the Gold Coast for some garden-walking.
Chicago’s Latin motto, Urbs in Horto means "City in a Garden." Some of Chicago’s finest private gardens are along North Dearborn Parkway, a block west of State and the Cardinal’s Residence. You can follow Dearborn back to Division St. and catch a subway train back to the Loop, or, better yet, turn back north and visit Lincoln Park