Old Town: Historic Charm Amid Urban Bustle

If you’re looking for a nice little neighborhood that thrives on its own, Old Town might be for you. Old Town has changed a lot during the last few decades, and has an interesting history of rich and poor, hippie and professional, legal and illegal (the illegal Blues Brothers Bar operated in Old Town on Wells Street). Much of the area’s streets and alleys do not follow the grid pattern established after the Great Chicago Fire since it experienced less destruction than many other areas of the city, which adds to its distinctiveness. This small neighborhood is known for its affluence, upscale (though not necessarily uppity) offerings, and an abundance of independently owned businesses.

In Old Town you can get yourself into a traditional apartment, converted loft, or possibly a town home rental. On average, a studio goes for about $1,100, a one bedroom apartment is near $1,400, a two bedroom averages $1,800, and a three bedroom for about $2,100.

Start your summer with the impressive, juried Old Town Art Fair, then stomp your way into fall at the Wine Crush in Old Town grape-stomping competition, and reward yourself with a wine tasting afterward. Wet your pants at Chicago’s famed Second City comedy venue, where tons of SNL folks got their start, then mix it up and take in some dinner theatre at the Noble Horse Theatre, a horse theatre which is housed in the only remaining horse stable in Chicago.

Although the neighborhood of Old Town is small, public transportation is very accessible. The Red Line stops at North/Clybourn, and a bit further east the Brown Line stops at Sedgwick; both the Red and Brown lines can be taken south to the Loop or to Fullerton, where you can transfer to the other line if need be. City buses run along the major streets of Clark, Halsted, and North in Old Town.