Old Town

Those who stay true to roots would argue that Old Town is confined solely to the enclave of narrow, pre-grid, horse-and-buggy streets tucked into the southeastern corner of Lincoln Park. At this point, most would agree that Old Town now includes a swath of territory south of North Avenue, on and around Wells Street. Everyone would agree that the location is enviable, with the close proximity to downtown, to Lincoln Park, and to Lake Michigan.

There's a lot going on here. Food-wise, there are outstanding food options, with pretty much any cuisine covered and bars, lots of bars, even for Chicago. When you shop the various and sundry boutiques, the proprietor is likely to be a second, third, or fourth generation owner, and you'll find such stuff here as fudge, pipe and tobacco goods, spices, and one of the country's most renowned aquarium specialty stores. Entertainment options are rich, thanks to Second City (one of the country's premier improvisational venues), Zanie's (with its consistently rich lineup of comedians), and the Piper's Alley Cinemas. Oh, and don't forget to spend a day at the annual Old Town Art Fair.

For renters, there are courtyard and low-rise apartment buildings and converted lofts. There is no convenient el station, although the buses run fairly reliably down Clark Street and North Avenue, allowing for brief rides to the el.