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East & West Old Town

Wedged between Lincoln Park and the Gold Coast, Old Town offers the best of both of these neighborhoods and shines with a serious charm of its own. Appropriately named, this community boasts a big chunk of Chicago history, with many of its homes and buildings dating back to the Victorian era.

You’ll notice that some of Old Town’s streets don’t fit into Chicago’s navigational grid; that’s because they predate the Great Chicago Fire. In fact, there’s even a landmark here that went untouched by the catastrophe. That’s right, St. Michael’s Church was one of the few buildings still standing after the flames.

Years after the Great Fire, Old Town became a melting pot for artists and musicians. Small studio spaces were built to house students of the nearby Art Institute of Chicago and folk musicians like Janis Joplin and Mama Cass frequented local venues. Eventually things calmed down and the energetic scene became more of a mecca for families and young urban professionals.

Despite it being one of the smaller neighborhoods of Chicago, Old Town offers the world at your fingertips. The streets are lined with a diverse array of restaurants, coffee houses and eclectic shops. Boutiques offer a more personalized shopping experience than those at big-name department stores and specialty shops range in everything from exotic spices to rare books.

In recent years, a few chain restaurants have reared their way into Old Town, but local cafes and authentic eateries still thrive in this historic spot. Neighborhood pubs are not only inviting, but also a great place to mingle after catching a show at the world-famous Second City Theatre. Cast members of Second City frequent some of these bars and have been known to strike-up conversations with theater enthusiasts. When you do feel like breaching the border of Old Town, you can hop on the Brown or Purple line at the North Sedgwick El station. 

he majority of residential Old Town is compromised of townhomes and single-family brick-style units. Most homeowners here have gone to great lengths to renovate and restore these homes to resemble their original structures. Because of its vintage charm and close proximity to the Loop, this neighborhood is prime real estate for the affluent. However, rents are still a notch below those of the Gold Coast.

Interested in Old Town real estate? Old Town Restaurants & Bars
Old Town Resources Old Town Schools
Old Town Shopping  

Dining in Old Town

Flat Top Grill
1000 W Washington Blvd
Cuisine: American
Bistrot Margot
1437 N Wells St
Cuisine: French
Adobo Grill
1610 N Wells St
Cuisine: Mexican
Dinotto Ristorante
215 W. North Avenue
Cuisine: Italian
Father and Son Pizza
645 W North Ave
Cuisine: Pizza
1401 N Wells St Fl 1
Cuisine: Italian
Cafe Sushi
1342 N Wells
Cuisine: Japanese/Sushi
Las Pinatas Mexican Food
1552 N Wells St
Cuisine: Mexican
1252 N. Wells St.
Cuisine: Mexican
Old Jerusalem Restaurant
1411 N Wells St
Cuisine: Middle Eastern
Kamehachi Cafe
1400 N. Wells
Cuisine: Sushi
Fireplace Inn
1448 N. Wells
Cuisine: American
Burton Place
1447 N. Wells
Dragon Room
809 W. Evergreen
1446 N. Wells
North Park Tap
313 W. North
Old Town Ale House
219 W. North
1240 N. Wells
1555 N. Dayton

Resources in Old Town

Chicago Police-Public Housing
365 W. Oak
Near North Police
1160 N. Larabee
Fire Department Breathing Apparatus
044 N. Orleans

Shopping in Old Town

Atom Antiques
1219 N. Wells
Barbara's Bookstore
1350 N. Wells
Crate & Barrel Outlet
800 W. North
1427 N. Wells
See Hear Music
217 W. North
1343 N. Wells
The Spice House
1512 N. Wells
Vagabonds Boutique
1357 N. Wells

Schools in Old Town

Catherine Cook School
226 W. Schiller
Edward Jenner School
1009 N. Cleveland
Franklin Fine Art Center
225 W. Evergreen
Byrd School
363 W. Hill
Schiller Elementary
640 W. Scott
Sojourner Truth School
1443 N. Ogden
Walter Payton College Prep
1034 N. Wells