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[title]1870s–1900
In 1870, Charles and Joel Wicker purchase 80 acres of land along Milwaukee Avenue. It becomes a desired address as families look to rebuild after the Great Chicago Fire of 1871. Initial immigrants include Germans and Scandinavians. Hoyne Street becomes known as Beer Baron Row due to the large number of brewer owners who build residences on the street.
Originally coined an “old-fashioned” in 1880 (by a Chicago newspaper no less!), this classic libation can be found today at the speakeasy-ish Violet Hour (1520 N Damen Ave, 773-252-1500), whose version mixes Weller 107, Demerara Syrup and Angostura Bitters.
Yep, Wicker Park and Bucktown both predate e-mail, fax machines and even the telephone. Return to the art of letter writing at Paper Doll (2027 W Division St, 773-227-6950), where it’s fun to check out and feel paper products from the likes of Egg Press, Spark, Bella Figura, Smock, Alee & Press, Tag & Co., Sugarcube Press, and the Happy Envelope.
1900–1930s
Jews and Poles migrate to the area, so much so that Wicker Park also becomes known as the Polish Gold Coast. Migrating Poles bring with them a large number of goats, giving Wicker Park’s sibling nabe the affectionate name Bucktown. In 1929, the stock market crashes, ushering in a period of decline.
The Division Street Russian and Turkish Baths, which opened in 1906, were once a fashionable place for men and women to enjoy a traditional schvitz. At Red Square (1914 W Division St, 773-227-2284), a newly renovated spa, restaurant and cafe that has taken over the former bathhouse, staffers are on hand to give you a healing plaitza or “rub” just like the locals enjoyed back then.
This was Al Capone’s town at one time. To get a taste of Chicago during the roaring twenties, pick up a fedora or cloche at Goorin Bros. (1533 N Milwaukee Ave, 773-384-4287) or a flapper dress at Store B Vintage (1472 N Milwaukee Ave, 773-278-7130) or Vintage Underground (1834 W North Ave, 773-252-4559).
1960s–1970s
The Kennedy Expressway is completed in 1960 and a new wave of settlers, priced out by gentrification in Old Town and Lincoln Park, move to the area. As the city’s overall population declines, the area continues to fall into disrepair.
Mid-century Chicago is alive and well at Corbett vs. Dempsey (1120 N Ashland Ave, third floor, 773-278-1664), a gallery that specializes in living artists who came of age in the ’50s, ’60s and ’70s like Karl Wirsum and Diane Simpson.
For a blast from Chicago’s soul past hit Danny’s Tavern (1951 W Dickens Ave, 773-489-6457) for its monthly Soul Night or build your own collection by thumbing through the extensive LP collection at Reckless Records (1532 N Milwaukee Ave, 773-235-3727).
1980s–1990s
Attracted by cheap rents and proximity to the Loop, a new wave of artists and young urban professionals move into both neighborhoods. In 1989, the now defunct Around the Coyote arts festival is established, and businesses like Soul Kitchen, Okno and Red Dog become neighborhood fixtures.
The Wormhole wears its reverence to blockbuster films of the ’80s right on its sleeve. If you don’t believe us, check out that giant DeLorean (a nod to the Back to the Future franchise) staring at you near the back of the cafe. There’s nothing retro about the beans (they’re provided by local roasters HalfWit), or the snacks by Fritz Pastry, but all this café needs is a sequel location to make its ’80s transformation complete.
Nothing says the ’80s quite like the rise of video games. While you’ll have to dig up your old Atari for a round of Pong, at Emporium Arcade Bar (1366 N Milwaukee Ave, 773-697-7922), you can chug one of two dozen beers on tap while trying your hand at Reagan-era classics such as Frogger, Donkey Kong, Q-Bert and Rampage.
2000s–present
Development and gentrification continue. Milwaukee Avenue, Division Street, Damen Avenue and North Avenue are lined with some of the most cutting-edge shops, restaurants, galleries and spas in the city.
What exactly is that futuristic Milwaukee Avenue storefront that glows like Mars? It’s the Mercury Method (1444 N Milwaukee Ave, 773-661-2994), a high-energy fitness technique in which participants workout in an environment heated to 98.6 degrees. Is it really the wave of the future? Only lean bodies and sound minds will tell.
Despite what theme parks might try and tell you, the ice cream of tomorrow isn’t Dippin’ Dots, it’s iCream (1537 N Milwaukee Ave, 773-342-2834), a local café where patrons custom create their own frozen treats on demand using an in-house liquid nitrogen machine. You say you want a non-fat, soy-based, root-beer ice cream topped with gummy bears and granola? You got it.