Wicker Park is an artists’ community filled with trendy shops, funky restaurants, and side streets lined with pricey mansions and other examples of Victorian architecture. Bucktown, traditionally working-class, is alive with new development. Both are favorite nighttime destinations of Chicagoans in search of the latest and greatest clubs and bars, but many don’t get to see the neighborhoods’ historic architecture, which is best viewed during the day.

START: Take El’s Blue Line to Damen station, then go 1 block south to Wicker Park.

1. Wicker Park: One the smaller parks in the city (a mere 4 acres) gave its name to one of Chicago’s most famous neighborhoods. The park was donated to the city around 1870 by siblings Charles (an alderman who made his money building railroads) and Joel Wicker. The brothers had extensive real estate holdings in the area and figured the park could only enhance the value of their property. At the intersection of N. Damen Ave. and Schiller St.

2. 1959–1961 W. Schiller St.: This double home was built in 1886 in the fashionable Second Empire style (note the large mansard roof and decorative sawtooth pattern in the brickwork). Its owner was a ship’s captain and medical doctor. In the 1920s it became a rooming house. It has thankfully been restored with lively Victorian colors.

3. 1951 W. Schiller St.: Built as the residence of Dr. Nels T. Quales, a Norwegian immigrant and humanitarian who founded Chicago’s Lutheran Deaconess Hospital, this house dates from 1873 and features Italianate styling and a Romanesque exterior noted for its use of arches and truncated columns. The addition of Moorish windows on the first and second stories altered the facade around 1890, and the house is currently being restored to its original condition.

4. Harris Cohn House: This mansion (built in 1890–91) was the home of a partner in the Cohn Brothers Clothing Company. The Italian Romanesque facade features square columns of granite (polished to resemble marble) and a turret resting on a shell-shaped base. Stonework on the second-floor balcony follows a checkerboard pattern, and handrails are scrolled with a motif of oak leaves. The residence was reconverted from a boarding house into a single-family home after a fire damaged it around 1980, and underwent extensive interior restoration and beautification in the 1990s. 1941 W. Schiller St.

5. Nelson Algren House: The exterior stonework on this three-story home is worth a look, but more interesting than the facade is the fact that novelist Nelson Algren (1909–81) lived in one of the building’s third-floor apartments from 1959 to 1975. The National Book Award winner (for his landmark The Man with the Golden Arm) and journalist drew inspiration for his writing from the surrounding neighborhood. A sidewalk marker provides info about Algren’s life and writings. 1958 W. Evergreen St.

6. Pritzker School: This Chicago public school is named for its most famous alumnus. A. N. Pritzker, the son of a Russian immigrant, grew up in the neighborhood and graduated from this school when it was known as Wicker Park School (Pritzker’s family went on to found the Hyatt hotel chain). 2009 W. Schiller St.

7. 1407 N. Hoyne Ave.: In the late 19th century, so many brewers built mansions along the stretch of Hoyne running from Evergreen Avenue to North Avenue that it became known as Beer Baron Row. This mansion, built in 1880 by German wine merchant John Rapp, was the largest single-family estate in Wicker Park at the time (the estate’s Coach House is now a separate residence at 2044 W. Schiller St.). The mansard roof and wrought-iron fence are characteristic of the Second Empire style of the estate. For all of its grandeur, however, this was not a happy home: Rapp was murdered here by his bookkeeper, his wife went insane, and their son was convicted of embezzlement. Note that locals refer to this place as either the Goldblatt or Wieboldt Mansion, though no member of these two prominent Chicago mercantile families (both Wicker Park fixtures) ever resided here.

8. 1521 N. Hoyne Ave.: German manufacturing executive Adolph Borgmeier was definitely behind the design of this fetching mansion, built in 1890 (though some claim it was actually built by a war profiteer who scammed the federal government for millions during the Civil War). The design is a brilliant mix of Romanesque and Queen Anne elements; look closely at the metal trim, and you’ll spot a host of decorative symbols (flowers, scrolls, and so on). The likeness of a woman carved into the exterior is a typical embellishment on German-built houses.

9. 1558 N. Hoyne Ave.: Ever fearful of another conflagration after the events of the Great Fire of 1871, the designers of this 1877 mansion stuck to ornamental pressed metal when creating its decorative trim. The Queen Anne–style home was originally built for Hermann Plautz, the president of the Northwestern Brewing Company. From 1927 to 1972, it served as the headquarters for the local American Legion (which is why that seemingly out-of-place cannon is still in the front yard).

10. Hermann Weinhardt House: When furniture company exec Hermann Weinhardt commissioned a home that would remind him of his German roots, this must-see mix of fairy-tale Victorian and Bavarian gingerbread was the result. The 1888 mansion features three stories of extraordinary detailing, including an elaborately carved balcony and an unusual juxtaposition of green stone and red-brick limestone. 2135 W. Pierce Ave. (btw. N. Hoyne Ave. and N. Leavitt St.).

11. Hans D. Runge House: This 1884 home, built by the treasurer of the Wolf Brothers Milling Company, is considered a prime example of the intricate Eastlake style (named for 19th-c. English designer Charles Eastlake) of ornamentation, and it features lots of elaborate woodwork. Architecture aside, the house is best known for a 1930 concert given by the great Polish pianist and statesman Ignacy Paderewski from the upper level of the building’s two-story porch, when the home functioned as the Polish consulate. 2138 W. Pierce Ave. (btw. N. Hoyne Ave. and N. Leavitt St.).

12. 2156 W. Caton St.: Import-export entrepreneur Ole Thorpe built this German-influenced Romanesque mansion in 1892. The most obvious feature is the round, domed turret rising from the flared and rough-surfaced foundations. Other highlights include a host of stained-glass windows and a notable sunburst design over the door on the second-story porch.

13. Flat Iron Building: Wicker Park is known for its artistic bent, and this office building, designed in 1929 by the firm of Holabird & Root, is best known as the home of many artists’ lofts and galleries (most are open to the public, so feel free to wander around inside). 1569 N. Milwaukee Ave. (at W. North Ave.).

14. Luxor Baths: Also known as the North Avenue Baths, this building dates back to the 1920s, when public baths were all the rage. The baths were a popular meeting spot for wheelers and dealers back in the day, and, according to legend, were also a mob hangout. The gleaming terra-cotta exterior is all that remains of the past; the interior has been transformed into a bunch of private yuppie apartments. 2041 W. North Ave.

15. Northwest Tower Building: One of the finest examples of Art Deco architecture in Chicago, this handsome 12-story building, which is now a trendy hotel called The Robey, was built in 1929 and was the tallest structure outside of the downtown area at the time. During the Prohibition era, the building was the terminus for a secret underground tunnel (now closed) that allowed patrons to escape a speak-easy across the street during raids. 2018 W. North Ave. www.therobey.com.

16. 1934 W. North Ave.: The coolness quotient of the Wicker Park/Bucktown area may have soared in 2001, when MTV selected it as the site of that season’s hit reality soap opera, The Real World, but quite a number of locals were anything but thrilled by the accompanying publicity. This Wicker Park loft apartment will be familiar to viewers as the spot where the young and the restless lived during filming (several of the seven cast members worked a few doors down, at the hip pizzeria Piece.

17. Window-shop along Damen Avenue: The best way to travel from Wicker Park into Bucktown is to window-shop along Damen Avenue, the street that marks the heart of the neighborhood. Start at its intersection with North Avenue and work your way up. The busy thoroughfare is loaded with vintage and designer clothing stores, cozy coffee shops, and trendy bars. Good shopping bets include p45 and Scotch and Soda. It’s also fabulous for people-watching.

Refresh and refuel at Mindy’s Hot Chocolate, a sophisticated sit-down restaurant where you can go sweet (the namesake hot chocolate and ridiculous desserts, like hot fudge cream puffs) or savory (an awesome burger as well as fancier fare, ranging from seafood to roast duck). And you can’t go wrong with a boozy hot chocolate. 1747 N. Damen Ave. tel. 773/489-1747. www.hotchocolatechicago.com. $–$$.

18. St. Mary of the Angels: The dome on this Renaissance-style Roman Catholic church dominates the neighborhood’s skyline, and was modeled on the Vatican’s St. Peter’s Basilica. The immense building—it takes up an entire block—opened in 1920 to serve Bucktown’s Polish parish, but by the 1980s had deteriorated to the point that it had been slated for demolition. A massive outcry from the local community led instead to a huge restoration campaign (the repairs cost more than the price of the original construction). Today, the dome of the church has been renovated, and the rest, from the carved angels on its rooftop to its stained-glass windows, is in picture-perfect shape. 1850 N. Hermitage Ave. (at W. Cordlandt St.). tel. 773/278-2644. www.sma-church.org.






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.