Old Town is an eclectic residential neighborhood that mixes frame cottages, brick town houses, historic taverns, and churches. Home to the city’s German immigrant population at the turn of the 20th century, Old Town became famous in the '60s as a hippie haven (a time that saw the birth of the area’s most famous landmark, The Second City comedy theater). After falling down on its luck in the '70s, the area has reinvigorated and is now a top destination for boutique shopping, dining, and theater.

START: Intersection of Clark St. and North Ave. Bus: 22 (Clark)

1. Germania Club: This lovely red-brick building, built in 1889, was the original home of a German-American Sangverein (singing society), a social outlet for immigrants in Chicago. Today, it’s home to a Starbucks. Note the elaborate terra-cotta ornamentation on the exterior and the oversize, arched windows on the second floor. 1536 N. Clark St.

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2. The Moody Church: Dwight L. Moody came to Chicago from Massachusetts in 1856 to work as a shoe salesman, but eventually became one of the city’s most colorful evangelists. He worked as a missionary mostly in the city’s poorer sections, notably the area that later became known as Cabrini Green, one of the nation’s most notorious housing projects (once located at Clybourn St., Cabrini Green is disassembled, and its residents have moved to low-rise, mixed-income housing). The church he founded was originally at Chicago Avenue and LaSalle Drive, where the Moody Bible Institute is now located. This building, dating from 1925, incorporates Byzantine (the decorative exterior) and Romanesque (the arched stained-glass windows) designs. Visitors are welcome to attend services. Free campus tours are offered Monday through Friday at 11am. 1635 N. LaSalle St. Tel: 312/327-8600. www.moodychurch.org.

3. Crilly Court: Resembling homes in an old quarter of New Orleans (complete with wrought-iron balconies in the back), these well-maintained row houses sit on one of Chicago’s oldest streets. The houses (and the apartment buildings opposite them) were built by contractor Daniel F. Crilly around 1885, when he cut a lane, named it for himself, and offered cottages to working families on the lower end of the economic scale. The owl-eyed among you might spot the names of the Crillys’ children carved into the entrances to the Queen Anne–style buildings. Block of Eugenie St., just west of Wells St.

4. 315 & 319 W. Eugenie St.: These privately owned homes are excellent examples of the wooden dwellings built outside the city limits in the years immediately following the Great Fire of 1871 (wooden buildings were outlawed in the city proper following the conflagration). They are noteworthy for their fanciful exterior trim work, not a rare sight in this immigrant neighborhood, where so many skilled artisans once made their homes.

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Stop in for the famous ribs at Twin Anchors Tavern, a neighborhood watering hole. This down-home spot, decorated with memorabilia dating back to the days when Frank Sinatra was a frequent visitor, is a favorite of locals. 1655 N. Sedgwick St. Tel: 312/266-1616. www.twinanchorsribs.com. $–$$.

5. Anton Franzen House: This classic Chicago cottage measures a story and a half and features a broad gabled facade. Built in 1880 of brick (as opposed to the prevailing wood), it is not so different in appearance from Frank Lloyd Wright’s original Oak Park cottage. If you want to see a prime example of the typical late-19th-century Chicago house, this is it. 1726 N. Hudson Ave.

6. St. Michael Church: It’s said that if you can hear the bells of St. Michael Church, you know that you’re in Old Town. Historically a German parish (as opposed to the Irish parishes found elsewhere in the city during the early 1900s), St. Michael is a massive Romanesque church that reveals a strong Southern European influence. The latter is especially evident in the stained-glass windows, embellished with Catholic iconography, that were imported from Munich at the turn of the 20th century. 1633 N. Cleveland Ave. (btw. North Ave. and Eugenie St.). Tel: 312/642-2498. www.st-mikes.org.

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7. A New Leaf: North Wells Street offers great window-shopping, and this store is a standout. The loft-style space is filled with cut flowers, vintage plant varieties, tropical foliage, succulents, and everything else you need to make a house a home, including candles in a rainbow of colors, ribbons to match, votive holders, and other tabletop necessities. 1818 N. Wells St. Tel: 312/642-1676. www.anewleafchicago.com.

8. Piper’s Alley: This entertainment space was the site of a bakery owned by Henry Piper in 1880. During the 1960s, it was Old Town’s most popular tourist zone, filled with boutiques and bead shops. Today it’s home to an art film cinema, several theaters and shops, and, since the 1950s, The Second City comedy club. 1616 N. Wells St.

9. The Fudge Pot: Walking down the steps to this chocoholic’s dream shop is a little like stepping back in time. It’s been here since the ‘60s, and the Wonka-like treats are made in house. The chocolate artists can create just about anything you dream up in cacao form, including the face of Abraham Lincoln. 1532 N. Wells St. Tel: 312/943-1777. www.thefudgepotchicago.com. $.

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10. West Burton Place: What was once a short block of cookie-cutter Victorian homes was remodeled in 1927 into inspired apartment buildings by Sol Kogen and Edgar Miller, two Old Town artists who had studied together at the Art Institute in 1917. The heavily embellished structures were rehabbed with an assortment of salvaged materials (glass, marble, terra-cotta, etc.) from various demolished buildings in the area. Miller’s masterpiece is 155 W. Burton Place (observe the bounty of transparent stained glass—Miller’s favorite medium). At the time of writing, a unit here was for sale for a cool $1.5 million, if you’re interested in moving in.

11. Chicago History Museum: Founded in 1856, the History Museum is one of Chicago’s oldest cultural institutions, and, somewhat secretly, one of the best. Its handsome Georgian red-brick headquarters underwent a massive renovation in 2006. The galleries feature interactive exhibits, including a re-creation of an 1890s El station; an exhibit on “Facing Freedom in America” (covering everything from women’s suffrage to Japanese internment); and a section on Illinois’s most famous native son, Abraham Lincoln. There’s a special gallery just for kids, where you can dress up like a giant Chicago hot dog with all the fixings and admire yourself, hot peppers and all, in the mirror. 1601 N. Clark St. (at North Ave.). Tel: 312/642-4600. www.chicagohistory.org.

 

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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.