Old Town

CHICAGO, IL

Despite its name and historic roots, Old Town is a mix of old and new. Victorian-style buildings, modernist architecture, trendy cafes, sports bars and busy comedy bars all coexist in a small neighborhood just south of Lincoln Park. Residents love the mellow atmosphere and proximity to the lakefront. And for buyers who want more affordable apartments, Old Town is a great place to look.

Old Town residents can take the CTA’s Brown and Purple lines to the Loop, suburbs, or Ravenswood. The Red Line also runs through Old Town to the north and south sides.

• Historic landmarks. Old Town retains some of its historic buildings, including a few churches, a design studio, and Germania Place, a century-old hall where German immigrants in the 19th century stayed which now feature immersive exhibits such as Monet and Van Gogh.

• Food and drink. Old Town Pour House is the quintessential neighborhood bar, decorated with niche art and frequented by locals from all walks of life. Other spots worth a visit include pastry haven cocoa + co, Frank Sinatra-favorite Twin Anchors, lively pizza place Happy Camper Pizza; Mexican eatery Adobo Grill; Kamehachi for some of the best sushi Chicago has to offer; and two of Wells Street’s Italian staples, Orso’s and Topo Gigio.

• A breeding ground for some of the greatest names in comedy. One of the longest-standing improv theater troupes in Chicago, The Second City is considered a breeding ground for some of the greatest names in comedy. Zanies is a popular bar which constantly features new and old talents. Utopian Tailgate is a rooftop bar that has fun activities such as super-sized Jenga, drinking games, disco dance party, and more with elevated eats and whimsical drinks; and Bastu, a fun bar and lounge where comedians compete in challenges of all kinds with the losers receiving a punishment.

Old Town offers a variety of housing options, from vintage walk-up apartments to luxurious high-rise condos with views of the lake. There are also a number of single-family homes, new construction multi-units and brick townhomes available, and you’ll find a few brownstones next to storefronts.