Off the Beaten Path Chicago: Portage Park and Jefferson Park

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Most visitors to Chicago explore its downtown attractions and well-known nightlife areas, such as Wrigleyville to the north and Wicker Park on the Northwest Side. However, while they are great places to visit, Chicago has much more to offer.

Portage Park and the adjacent Jefferson Park are two diverse neighborhoods that offer quality entertainment without the crowds. You can reach them from downtown on Blue Line trains and Milwaukee Avenue buses. Both Portage Park and “Jeff Park,” as the far Northwest Side neighborhood is often called, are transforming from strictly residential areas to Chicago’s next hub of cultural activity. Here are a few places that are worth the trek.

The Gift Theatre

Don’t judge a book by its cover, or . . . a theater by its square footage. The intimate, 50-seat venue in Jefferson Park is small on space, but big on production value. Co-founded in 2005 by neighborhood resident Michael Patrick Thornton and his University of Iowa classmate William Nedved, the Gift introduced live theater to the area. Since then, the ensemble company has staged a number of world premieres and award-winning plays. If you like improvised comedy, catch Natural Gas performances on Wednesday nights.

Fischman Liquors and Tavern

After catching a show at the Gift, walk a few feet to this laid-back neighborhood bar/store for one of the best selections of craft beer and microbrews in Chicago. Take a seat at the counter and you might spot familiar faces from the theater, as the ensemble often meets at Fischman‘s post-performance. The Jefferson Park staple also hosts live music, trivia nights, and a weekly food truck rally outside.

Filament Theatre

A fixture in Portage Park since 2014, this formerly itinerant group is helping transform the area into Chicago’s new arts destination. In addition to diverse plays, staged in the former furniture warehouse, Filament hosts concerts and community events. The company is focused on green practices and “creating theatre in a folk tradition.” After taking in a performance, check out the neighboring businesses along Milwaukee Avenue.

Portage Theatre

Across the street from Filament is the historic Portage Theatre. With its Art Deco marquee, it’s a popular fixture of Portage Park. Built in 1920 as a movie theater, it’s one of the oldest venues of its kind in Chicago. These days, it hosts music performances, film screenings, and private parties in a grand auditorium designed in the Beaux-Arts opera house style. In 2013, Portage was granted landmark status by the city.

Portage Grounds Coffee

This bright, airy cafe—located across the street from the scenic 36-acre Portage Park—is a favorite gathering place of neighborhood residents. On a typical visit, you may run into lounging families, artists, musicians, study groups, or even running clubs. Bring a book to read in front of the fireplace, or sit by the tall windows to get some sun. If you visit Portage Grounds in the summer, enjoy your java on the outdoor patio. Besides coffee from Chicago’s Passion House Roasters, the café serves tea, seasonal drinks, and locally-made baked goods.

  • Fischman Liquors and Tavern

    4780 N Milwaukee Ave, Chicago, IL 60630, United States

    (773) 545-0123

  • Filament Theatre

    4041 N Milwaukee Ave, Chicago, IL 60641, United States

    (773) 270-1660

  • Portage Theatre

    4050 N Milwaukee Ave, Chicago, IL 60641, United States

    (773) 283-7244

  • Portage Grounds

    5501 W Irving Park Rd, Chicago, IL 60641, United States

    (773) 930-3693

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