Begin your walk at the (1) Michigan Avenue Bridge (Michigan at Wacker Drive)
over the (2) Chicago River, the flow of which was famously reversed in 1900 to keep sewage from flowing into Lake Michigan, the source of the city's drinking water. On the north bank, two important buildings square off across the street from one another, the gleaming white, terra cotta tiled (3) Wrigley Building (400-410 N. Michigan Avenue; www.wrigley.com/wrigley/about/about_story_building.asp) of the 1920s to the west, and the Gothic looking (4) Tribune Tower (435 N. Michigan Avenue) to the east. With flying buttresses at the top of the building that mimic the Rouen Cathedral of France, the Trib Tower only looks ancient; it was the winning design in a 1922 competition. Take a closer look at the façade, which is embedded with 120 stones from famed sites around the world-China's Great Wall, for example-and each of the 50 states, such as Massachusetts' Bunker Hill.
Across from the Trib Tower look for a staircase that leads to Lower Michigan Avenue and the famed (5) Billy Goat Tavern (430 N. Michigan Avenue; www.billygoattavern.com), a subterranean hole-in-the-wall long patronized by local journalists and made famous in the 1970s by actor John Belushi's classic "Cheezborger, Cheezborger" skit on "Saturday Night Live." No Pepsi, Coke!
Return topside and continue your stroll north until you are opposite the (6) InterContinental Chicago hotel (505 N. Michigan Avenue), originally built as the Medinah Athletic Club in 1929. It's worth a peek inside to see the greeting "Es Salumu Aleikum" or "Peace be to God" etched into the marble entryway and the ornate interiors including a terra cotta fountain at the top of the marble stairway.
Back outdoors, northbound, this section of the Mag Mile is home to luxury designer shops like Polo/Ralph Lauren, luxe department stores such as Neiman Marcus, and vertical malls. At Chicago Avenue you'll find the area's lone public building survivors of the Great Fire of 1871 in the (7) Water Tower (Michigan and Chicago Avenues) and its 1869 sibling across the street, the Pumping Station, both in Gothic Revival style. A pleasant pocket park surrounds the Water Tower, a symbol of the city's determination, though critics have long questioned its architectural value including writer Oscar Wilde who called it, "a castellated monstrosity with pepperboxes stuck all over it."
Continue north to the (8) John Hancock Center (875 N. Michigan Avenue), a tapering 1970, 100-story skyscraper by architects Skidmore, Owings & Merrill. An observatory (www.hancock-observatory.com) on the 94th floor offers panoramic views. More relaxing, (9) The Signature Lounge (875 N. Michigan Avenue; www.signatureroom.com) on the 96th floor offers the same perch for the price of a cocktail. Finish your walk at (10) Oak Street Beach (Oak Street and Lake Michigan) via an underground passageway that marks the end of the avenue at the Lake Michigan shore.
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