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Post-Fire cottages and Crilly Court rowhouses in the landmark Triangle, with Wells Street carrying the restaurants and Second City anchoring the comedy corner of the city. The Sedgwick Brown Line stop puts the Loop nine minutes away.
Old Town sits between Lincoln Park and the Near North Side, with North Avenue as its spine street and Wells Street as its main strip. The heart of it is the Triangle, the wedge of narrow streets northwest of North and Wells where the street grid bends and the lots shrink to cottage scale.
The neighborhood grew up fast after the Fire of 1871 burned through, which is why so much of what stands here dates to the 1870s and 1880s. St. Michael’s, whose walls came through the Fire, still rings the hours over the Triangle.
The Sedgwick stop on the Brown and Purple Lines sits at Sedgwick and North, a short ride from the Loop in one direction and Lincoln Square in the other.
Lincoln Park itself begins at the neighborhood’s northeast corner, which puts the zoo, the Conservatory and the lakefront within a walk. Inside the neighborhood, the Menomonee Club and the small Triangle gardens carry the green; the district association keeps the courtyards and parkways famously well tended.
The Triangle is one of the city’s oldest landmark districts: wood workers cottages that beat the 1874 fire limits, brick Italianates, and the 1885 Crilly Court rowhouses, one of Chicago’s first planned residential courts. Landmark rules shape what owners can change on the outside, which is part of why the blocks look the way they do.
East and south of the Triangle the stock shifts to mid-century towers, courtyard condos and newer infill, so the same neighborhood covers both a vintage cottage and a high-rise two-bedroom.
The Old Town Art Fair has run in the Triangle every June since 1950, joined the same weekend by the Wells Street Art Festival, and Second City and Zanies keep the comedy calendar full year round.
Check our events calendar for current dates.
An easy first errand in a new place: the rooms locals have kept in business for decades, each checked as open when this guide was last updated.
The Fudge Pot · 1532 N Wells · map
Hand-made chocolate on Wells since 1963.
Twin Anchors · 1655 N Sedgwick · map
Ribs in a corner tavern that has been serving since 1932.
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From a landmark cottage in the Triangle to a high-rise with a lake view, Old Town covers more ground than its size suggests. Tell us what you are looking for and we will walk any building with you.
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