This scenic and exclusive neighborhood of leafy streets and historic mansions fronts Lake Michigan and is home to some of Chicago’s most famous and moneyed families. It dates back to the 1880s, when retailing wizard Potter Palmer built a lakeshore castle in the midst of what was then wild marshland (his spectacular home, at what is now 1450 N. Lake Shore Dr., was eventually torn down and a high-rise complex built in its place). After buying up the neighboring land, Palmer watched the city’s most prominent social families follow his lead, turning his marshland into real estate gold.

START: Oak St. Beach, Lake Shore Dr. just south of Oak St. Bus: 151.

1. Residence of the Roman Catholic Archbishop of Chicago: This 2 1/2-story Queen Anne–style mansion dates back to 1880 and stands on the grounds of a former cemetery. One of the oldest and most notable residences on the Gold Coast, it’s also one of the best preserved. Note the elaborate chimneys—there are 19 of them. The red-brick structure is the current home of Cardinal Blase Cupich. 1555 N. State Pkwy. (at North Ave.).

2. Madlener House: Designed as a private residence by Richard E. Schmidt in 1902, this National Historic Landmark foreshadowed the Art Deco style that would not emerge in Chicago for another 20 years. The brick-and-limestone structure’s clean lines and its doorways ornamented with delicate bronze grillwork offer hints of both the Prairie and Chicago schools of design. It’s currently home to the Graham Foundation for Advanced Studies in the Fine Arts, which has installed a collection of fragments from famous Chicago buildings in the courtyard. It’s a must for architecture buffs and historic home fans. Time: 30 min. 4 W. Burton Place. tel. 312/787-4071. Gallery/bookshop open Wed–Sat 11am–6pm.

3. Patterson-McCormick Mansion: Designed by New York architect Stanford White, this palazzo-style mansion was commissioned in 1893 by Joseph Medill, owner of the Chicago Tribune, as a wedding present for his daughter. The Georgian structure is faced with Roman bricks of burnt yellow and terra-cotta trim, and marked the beginning of an architectural movement toward classical exteriors. The home was purchased in 1914 by Cyrus McCormick, Jr., son of the inventor of the reaper and the first president of International Harvester. McCormick had it enlarged to its current size in 1927. The building now houses condominiums. 20 E. Burton Place.

4. 1525 N. Astor St.: This attractive town house (on a block full of multimillon-dollar homes) is the former home of Robert Todd Lincoln (1843–1926), the son of Abraham and Mary Todd Lincoln. Lincoln operated a private law practice in Chicago before moving on to serve as secretary of war to Presidents Garfield and Arthur. Upon the death of George Pullman, one of his clients, Lincoln became president of the Palace Car Company in 1897.

5. 1451 N. Astor St.: Designed by Howard Van Doren Shaw, who built several of the mansions on ritzy Astor Street, this mansion showcases the unique “Jacobethan” style (a mixture of 16th- and 17th-c. features of Elizabethan and Jacobean architecture). It was originally built for brewer Peter Fortune in 1912.

6. 1449 N. Astor St.: The origins of this grandiose château remain a mystery, though it was definitely built around 1890. The exterior features, including an intimidating stone porch, decorative friezes, and a large front bay, make for worthwhile viewing.

7. Charnley-Persky House: This 1892 National Historic Landmark was built by the firm of Adler and Sullivan, back when a 19-year-old draftsman named Frank Lloyd Wright was laboring there in obscurity. Wright’s role in designing the building (he called it “the first modern house in America”) is evident in its progressive shape, especially when compared to its fanciful neighbors, homes that drew on styles based in antiquity. Even today, this home is an excellent illustration of the timelessness of Wright’s ideas. Charles Persky donated the building to the Society of Architectural Historians in 1995, and the society runs public tours on Wednesdays (45 min.) and Saturdays (60 min.). Call for information. Time: 1 hr. 1365 N. Astor St. tel. 312/573-1365. Apr–Oct, tours are free Wed at noon; Sat tours at 10am and noon include other historic neighborhood residences and cost $10 adults, $8 seniors, and $5 kids 5–13.

8. Astor Court: If this building evokes images of England when you look at it, that’s because of its Georgian formality, typical of the architecture you’d find in London. It was designed in 1914 by Howard Van Doren Shaw. Look up at the ornament over the central drive, which leads to a formal inner court surrounded by residential units: The ornament is the source of the structure’s nickname, “The Court of the Golden Hands.” 1355 N. Astor St.

9. Playboy Mansion: Built in 1899, this very traditional-looking mansion was home to Playboy’s Hugh Hefner during his Chicago heyday in the 1960s. The building has been converted into very expensive private condos, so you’ll need your imagination to envision Hugh romping here with his bunnies and hosting legendary parties. (Playboy Enterprises no longer has a presence in Chicago; it’s now in Los Angeles.) 1340 N. State Pkwy.

10. 1310 N. Astor St.: John Wellborn Root (1850–91), one of the founders of the Chicago School of Architecture and a former director of the American Institute of Architects, is best known for his work on skyscrapers with Daniel Burnham (their collaborations include the Monadnock and Rookery buildings). But this lovely brick town house, built by Root in 1887, must have struck a chord with the architect—he moved in and lived here with his family (including his son, John Root, Jr., a renowned architect in his own right) until he died of pneumonia at the young age of 41.

11. Three Arts Club: This four-story Chicago landmark, which is now a Restoration Hardware retail store and cafe, was built in 1914 by architect John Holabird to house a club dedicated to providing women with a suitable environment for the study of painting, music, and drama. Many of the club’s founders were prominent women of the time, including social reformer Jane Addams and socialite Edith Rockefeller McCormick. The club’s residential units were arranged around a central courtyard, in the style of a Tuscan villa (a lot of the exterior ornamentation is also Byzantine in nature). The ornamental mosaics over the terra-cotta entrance salute the three branches of the arts that the club is named for. 1300 N. Dearborn St. 



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.