Many of Chicago’s signature buildings are found along the stretch of Michigan Avenue known as the Magnificent Mile. From private clubs to posh condominiums and historic churches, this entire area rose from the ashes after the Great Fire of 1871. Today, Michigan Avenue is one of the most architecturally significant avenues in the country. 

START: Chicago/State El Station or Bus 151 (Michigan Ave.) to Walton St.

1. The Drake Hotel

This landmark 13-story building was constructed in 1920 of Bedford limestone in a design inspired by the Italian palazzos of the late Renaissance. You can stroll through the ornate lobby or stop in for finger fare at the serene Palm Court, one of the city’s top spots for afternoon tea (call tel. 312/787-2200 for reservations).

Time: 20 min. 140 E. Walton Pl. El: Red Line to Chicago/State. 

2. Palmolive Building

This “monument to cleanliness” was built in 1929 for Colgate-Palmolive, the world’s leading soap manufacturer, but was known as the Playboy Building from 1965 to 1989, when it housed the famous skin mag (the publication moved to Los Angeles in 2012). The picturesque Art Deco landmark was Chicago’s first commercial skyscraper built outside the Loop. It now houses luxury condos.

Time: 5 min. 919 N. Michigan Ave. El: Red Line to Chicago/State.

3. Fourth Presbyterian Church

This church, built in 1914, was the creation of Ralph Adams Cram—America’s leading Gothic Revival architect, best known for New York’s Cathedral of St. John the Divine—and parishioner/architect Howard Van Doren Shaw. The church is an amalgam of English and French Gothic styles, while the parish buildings are Tudor in form. Check the website to see if a concert is playing while you’re here. The courtyard is a serene photo spot.

Time: 15 min. 126 E. Chestnut St. (at N. Michigan Ave.). El: Red Line to Chicago/State.

4. John Hancock Center

The first giant on the Chicago skyline was erected in 1969 and featured several structural innovations, including crisscross steel framing and a tapering form that creates an illusion of super proportions, making the building look larger than it is. At 360 CHICAGO, the 94th-floor observatory, a fairly new attraction called TILT—glass boxes that tip toward the ground—will get your heart pumping. For a tamer experience, grab a drink at the Signature Lounge on the 96th floor and you can skip paying admission (although drinks aren’t cheap).

Time: 1 hr., if you visit 360 CHICAGO. 875 N. Michigan Ave. tel. 312/751-3681. Admission to observatory varies by time: $21–$23 adults, $14–$16 children 3–11, free for children 2 and under; TILT $8. Daily 8am–11pm. El: Red Line to Chicago/State.

5. Chicago Water Tower and Pumping Station

Built in a castellated Gothic style, these two National Historic Landmarks, which sit across from each other on Michigan Avenue, were the only ones in the area to survive the Great Fire of 1871. Why the duo escaped unscathed when virtually every other building in the vicinity was wiped out remains a mystery. Made of a distinct yellow-tinted Illinois limestone, the buildings now house a city art gallery, the Lookingglass Theatre Company and Water Works, a sweet little public library. 

Time: 30 min. Michigan Ave. at Chicago Ave. El: Red Line to Chicago/State.

Take a break: For a drink, snack, or something more elaborate, head to Marisol, at the Museum of Contemporary Art. The menu is seasonal and therefore always changing, but you can expect artfully plated pastas, seafood, salads, and inspired dips, like sunflower hummus. 205 E. Pearson, in MCA. tel. 312/799-3599. $$–$$$.

6. Woman’s Athletic Club

Modeled on elegant Parisian buildings, this 1929 creation of Philip B. Maher (1894–1981) is marked by French Second Empire influences. The nine-story structure houses a private club and the oldest women’s athletic facility in the United States.

Time: 5 min. 626 N. Michigan Ave. El: Red Line to Grand.

7. Medinah Temple

Built in 1912, this Moorish-style palace was the regional headquarters of the Shriners and site of their annual circus until 1998. The building, one of the finest examples of the Islamic Revival style in the country, nearly fell into ruin before it was declared a historic landmark and restored as a Bloomingdale’s home furnishings store.

Time: 10 min. 600 N. Wabash Ave. El: Red Line to Grand.

8. Tree Studios

To encourage visiting artists working on the 1893 Columbian Exposition to stay in Chicago, this row of cottage-like buildings was built in 1894. The Queen Anne–style buildings feature retail stores on the street level and artists’ studios upstairs (the latter are closed to the public).

Time: 5 min. 601–623 N. State St. El: Red Line to Grand.

9. The Wrigley Building

The Wrigley family, of chewing gum fame, owns and operates this building, which was erected between 1919 and 1924. Its white, terra-cotta cladding (more than 250,000 tiles’ worth) glitters in the sunlight and reflects the water of the nearby river. Six shades of white, darkest at the base and lightening up to the roofline, distinguish the exterior tiles. The shading is especially beautiful when the building is illuminated after dark. Another highlight is the south tower’s immense, four-faced clock, which was inspired by the Giralda Tower in Seville, Spain.

Time: 15 min. 400 and 410 N. Michigan Ave. El: Red Line to Grand.

Take a break: During Chicago’s most glorious months (May–Sept), head down the steps at Dearborn Street and Wacker Drive to the Riverwalk. This beautifully landscaped 1.25-mile path takes you through floating gardens, under bridges, and past wine bars, restaurants, and patio cafes that burst at the seams with the happy-hour crowd. There’s been a lot of turnover since the reformed Riverwalk opened in 2016, but one reliable stop, generally open May through October, is Tiny Tapp & Cafe, an excellent, locally owned spot for wine, cocktails, and creative gastropub fare. 55 W. Riverwalk South; no phone;

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.