Old Town Limo

Getting Around Old Town

Old Town runs along North Avenue and Wells Street, just west of the Gold Coast, with the Second City theater and Piper's Alley as the landmark corner. Wells Street is the spine — the comedy clubs, the Old Town Ale House, the restaurants and the small shops in the triangle of low-rise blocks that survived the fire. The streets here are narrow and the triangle is one-way in spots, so drivers stage off the main drag and pull up to the theater door rather than fight for curb space on Wells before a show.

Second City and the iO theater drive a steady rhythm of show-night bookings — a ride down for the early set and a guaranteed pickup after, since the block clears out all at once when the show lets out. Old Town is also a favorite for bachelor and bachelorette nights working the Wells Street bars, where a party bus or stretch lets the group move between spots without splitting up. Date-night dinners along Wells, then drinks, then home is the other common pattern, and the neighborhood's walkable enough that one drop and one pickup usually covers it.

For airports, Old Town has quick access to both the Kennedy via North Avenue and Lake Shore Drive a few blocks east, so O'Hare runs are flat $130 sedan and Midway $130, with timing padded around the evening crush. The trips locals book most are Second City show nights, Wells Street bachelor and bachelorette circuits, and date-night dinners through the Old Town triangle.