Old Town runs along Wells Street on Chicago’s Near North Side, north and south of North Avenue, a block west of LaSalle. It is one of the oldest surviving parts of the city, it is the home of American improv comedy, and it has a run of restaurants and taverns that have been in the same rooms since before the Second World War. It is also small — you can walk the whole commercial strip in twenty minutes — which is exactly why it works.
The history that is still standing
German immigrants settled the area in the 1850s, and community life centred on St. Michael’s Church, which survived the Great Chicago Fire of 1871 — one of a handful of structures in the burn zone that did. Its walls held; the interior did not, and it was rebuilt inside the original shell.
The residential streets west of Wells hold the Old Town Triangle, one of the best-preserved concentrations of pre-fire and immediately post-fire housing in Chicago. Frame cottages, brick workers’ houses, narrow lots — the pattern the fire codes outlawed almost everywhere else in the city. It is a genuinely unusual walk and it costs nothing.
The Chicago History Museum sits at the neighborhood’s eastern edge on Clark Street at the corner of Lincoln Park, and it is the best single explanation of how any of this happened.
Comedy
The Second City on Wells Street is the oldest improvisational theatre troupe to be continuously based in Chicago and the single most important comedy institution in the United States. The list of people who came through it before they were famous includes Bill Murray, John Belushi, Chris Farley, Tina Fey and Chevy Chase, and it is still producing revues rather than trading on the past.
Tickets for the mainstage are worth booking ahead. The free improv set is one of the best-kept secrets in Chicago: every night except Friday, the cast returns after the last show and works without a script, and you simply stay in your seat at no extra cost. It typically starts around 10:30pm, so check when the final revue ends and plan accordingly.
Zanies Comedy Club at 1548 N. Wells Street, a short walk south, is the stand-up counterpart. Open since 1978, it is Chicago’s oldest stand-up club, and its alumni include Jay Leno, Jerry Seinfeld, Chris Rock, Kathy Griffin and Jimmy Fallon. It is a small over-21 room with a two-drink minimum and a booking policy that regularly puts nationally touring comedians in front of a very small audience.
Old Town is a small strip where a few closures change the whole evening.
Neighbors post what is actually happening right now — new openings, closings, wait times, and honest opinions. See what Chicago neighbors are saying or join free and ask them yourself.
Where to eat and drink
Twin Anchors has been open since 1932 and is the neighborhood’s most-cited room — barbecued baby back ribs, a tavern front, and a bar that has appeared in more Chicago films than most actors. It does not take reservations for small parties and the wait on a Saturday is part of the experience.
Old Town Ale House opened in 1958 across from Second City and became the after-show bar for the comedians, musicians and writers who worked the strip. Anthony Bourdain and Roger Ebert were both regulars. The paintings on the walls are the owner’s and they are as much a part of the room as the beer.
The rest of the Wells Street corridor between Division and Menomonee carries a long run of long-standing places: Nookies for breakfast, Topo Gigio and Orso’s for Italian, the Fireplace Inn, Adobo Grill, and Broken English Taco Pub. The Fudge Pot has been making chocolate on Wells since the 1960s, and The House of Glunz is one of the oldest wine merchants in the country, trading since 1888.
The Spice House is the other reason people make a specific trip here — a proper spice merchant with open jars, blends made in-house, and staff who will talk you through the difference between four kinds of paprika.
Getting there
The CTA Brown and Purple Lines stop at Sedgwick, which puts you at the northern end of the Wells Street strip. The Red Line at Clark/Division covers the southern end. From the Loop it is about ten minutes on the train, or a pleasant twenty-five-minute walk north along LaSalle.
Lincoln Park — both the neighborhood and the park itself, with the free zoo and conservatory — begins immediately north and east, which makes Old Town an easy first or last stop on a day built around either.
Living in Old Town
Old Town is expensive, and it is expensive for reasons that hold up: it is one of the most walkable parts of Chicago, it has three train lines within reach, Lincoln Park and the lakefront are minutes away, and the housing stock includes some of the oldest and most distinctive buildings in the city.
What residents mention as trade-offs are the size — the commercial strip is short, so a weekly shop means going elsewhere — and weekend noise on Wells, which carries a comedy-club and bar crowd from Thursday through Saturday. The residential triangle west of Wells is noticeably quieter than the blocks fronting it, and the price difference between the two is smaller than you would expect.
Frequently asked questions about Old Town, Chicago
Where is Old Town in Chicago?
On the Near North Side, along Wells Street north and south of North Avenue, a block west of LaSalle. The CTA Brown and Purple Lines stop at Sedgwick and the Red Line at Clark/Division, both about ten minutes from the Loop.
What is Old Town known for?
The Second City comedy theatre, some of the oldest surviving housing in Chicago in the Old Town Triangle, St. Michael’s Church which survived the 1871 fire, and a run of taverns and restaurants that have occupied the same rooms for eighty years or more.
Where should I eat in Old Town?
Twin Anchors at 1655 N. Sedgwick, open since 1932, for baby back ribs, and the Old Town Ale House at 219 W. North Avenue, open since 1958, for a drink. Nookies, Topo Gigio and Orso’s cover the rest of the Wells Street strip.
Is Second City worth it?
Yes, and the value is better than most people realise. Every night except Friday, a free improv set follows the last show — you stay in your seat and watch the cast work without a script at no extra cost, usually starting around 10:30pm. Book the mainstage in advance.
How long do I need in Old Town?
The commercial strip is walkable in about twenty minutes, so an afternoon covers the shops and the historic triangle, and an evening covers dinner and a comedy show. Many people combine it with Lincoln Park, which starts immediately north.
Is Old Town expensive to live in?
Yes — it is among the higher-priced Chicago neighborhoods, reflecting the walkability, transit access, proximity to Lincoln Park and the lakefront, and the distinctive older housing stock. The residential triangle west of Wells is quieter than the strip for a smaller price difference than most expect.
Old Town and Lincoln Park together
Old Town is small enough that most people combine it with Lincoln Park, and the two fit together neatly because they cover completely different needs.
Lincoln Park Zoo is free, open every day of the year, and one of the oldest zoos in the country. It is a fifteen-minute walk from the northern end of Wells Street. The Lincoln Park Conservatory next to it is also free and is the better option on a cold day — a Victorian glasshouse of palms, ferns and orchids that stays warm and humid through a Chicago February.
The park itself runs north along the lakefront from North Avenue Beach, which is the city’s oldest and busiest beach and about a twenty-minute walk east. The Alfred Caldwell Lily Pool, tucked behind the zoo, is a small landscaped hideaway that almost nobody outside the neighborhood knows exists.
The practical route: comedy or dinner in Old Town in the evening, zoo and conservatory in the morning, or the reverse. It fills a full day without a car and most of it is free.
Old Town through the year
Summer brings the Old Town Art Fair in June, one of the oldest juried outdoor art fairs in the country, which fills the residential triangle for a weekend and is worth planning around.
Autumn is the neighborhood at its best — the strip busy but not overwhelmed, the historic streets at their most photogenic, and comedy shows easier to book than in high season.
Winter suits Old Town better than most Chicago neighborhoods because so much of it is indoor and close together: a comedy show, a tavern that has been warm since 1932, and a chocolate shop within three blocks of each other.
Spring is quiet and cheap, and the easiest time to walk the Old Town Triangle without company.
Is Old Town safe?
Old Town sits among the lower-reporting parts of the Near North Side, and around three-quarters of Chicago’s neighborhoods rate A or B on the standard safety indices. Its immediate neighbours give useful bounds: the Loop reports an overall crime index of roughly 174 and River North around 176, both well above the national average and both inflated by huge visiting populations measured against small resident bases. Old Town has a much higher ratio of residents to visitors than either, and its numbers reflect that.
The realistic pattern is property crime concentrated on and around the Wells Street commercial strip late at night — vehicle break-ins, thefts from parked cars, occasional street theft as the comedy clubs and bars empty. The residential triangle west of Wells is quiet.
For a specific address, use the City of Chicago open data portal, which publishes every reported incident by type, date and block. Read the volume within two or three blocks, the incident type, the time of day, and the trend across a year or two rather than a single month. Then walk the block twice — once in daylight and once after dark — and look at lighting, foot traffic and whether cars on the street have items visible in them.