Old Town Chicago Walking Tour: History & Architecture Self-Guided Route

"Built in 1869 by German immigrants and gutted in the Great Chicago Fire just two years later, St. Michael's was rebuilt by 1873 using the original brick walls, which had survived the flames. Its twin spires, rising 210 feet, became a landmark used by disoriented residents to relocate their homes after the fire erased most street markers. The church anchored what was then a heavily German enclave, and the surrounding blocks still carry that immigrant-era street grid."

The church is generally open during the day for visitors; step inside to see the ornate German Baroque-influenced interior, which is more elaborate than the plain brick exterior suggests. There's no admission fee — a small donation is appreciated if you sit for a few minutes.

"The Old Town Triangle Historic District, roughly bounded by North Avenue, Ogden Avenue, and Larrabee Street, contains one of Chicago's densest clusters of pre- and post-Fire cottages. Many of the small wood-frame houses on Cleveland, Crilly Court, and Lincoln Park West were built quickly and cheaply by working-class families rebuilding after 1871, using salvaged materials and simple balloon-frame construction. The district was formally designated a Chicago Landmark in 1977, protecting the irregular mix of scale and setback that gives the area its patchwork feel."

Walk the interior streets slowly — Menomonee Street and Cleveland Avenue between Eugenie and Willow have some of the best-preserved cottages. Look for the small plaques on several houses noting construction dates; anything built before 1874 in this area is genuinely rare for Chicago.

"Developed in 1885 by real estate businessman Daniel Crilly, this short block introduced Romanesque Revival row houses on one side and a courtyard apartment building on the other, an unusual mixed-density layout for its time. Crilly's son later named the block's row houses' street after his father and reportedly courted controversy by carving family members' names into building cornerstones. The block survived mid-20th-century urban renewal efforts that razed much of surrounding Old Town, largely due to preservationist pushback in the 1940s and '50s."

It's a quiet residential street, so keep voices down — people live here. The row houses on the west side and the courtyard building entrance on the east are the two things worth stopping to actually look at closely.

"Opened in December 1959 at 1616 N Wells Street, The Second City grew out of the University of Chicago's Compass Players and pioneered long-form improvisational comedy as a legitimate theatrical form. Alumni include Alan Arkin, Joan Rivers, John Belushi, Bill Murray, Gilda Radner, Tina Fey, and Stephen Colbert — a list that essentially maps the last 60 years of American sketch comedy. The theater's original building burned in a 1967 fire and was rebuilt on the same stretch of Wells Street, where it's operated continuously since."

You don't need a ticket to appreciate the exterior and marquee, but if timing allows, evening shows run most nights and tickets typically range $30–$45. The building itself is unassuming — the history is the draw more than the architecture here.

"Founded in 1957, the Old Town School of Folk Music started in a storefront and helped launch the Chicago folk revival that ran parallel to what was happening in Greenwich Village. Its original Old Town location on Armitage Avenue (the school later expanded to a larger Lincoln Square building in 1998) hosted early performances tied to the neighborhood's brief run as a bohemian, countercultural center in the 1960s. Old Town's identity as an arts destination — separate from its immigrant and architectural history — largely traces back to this era."

The original building's exterior is worth a quick photo stop if you're tracing the folk-revival history, though most programming now happens at the Lincoln Square campus. Check the current schedule online if you want to catch a concert while you're in the neighborhood.

"Wells Street between North Avenue and Armitage was Old Town's main commercial spine through its various reinventions — German beer halls and shops in the 19th century, then head shops, boutiques, and music venues during the 1960s hippie era when the strip earned comparisons to San Francisco's Haight-Ashbury. Much of that countercultural retail energy faded by the 1970s as rents rose and the neighborhood gentrified, but a handful of longtime businesses and building facades still hint at that period. The mix of low-rise 19th-century storefronts with later infill gives the street an uneven, layered look that's mostly disappeared elsewhere downtown."

Walk the full stretch rather than cutting through — the storefront architecture varies block to block and rewards a slower pace. This is also where you'll find most of the neighborhood's shops and cafes if you want to browse before the meal stop.

"Operating since 1932 at 1655 N Sedgwick Street, Twin Anchors began as a corner tavern during Prohibition's tail end and became known for ribs after the current owners' family took over in 1978. Frank Sinatra was a regular in the 1960s, reportedly requesting the restaurant stay open late for him after Second City shows, and his corner booth is still marked. The building itself is a low brick corner structure typical of Old Town's pre-Fire commercial architecture, largely unchanged since it opened."

Ribs are the reason to come — expect a wait on weekend evenings since they don't take reservations for parties under six. Arrive by 6pm on weekdays to skip the worst of the line, and expect to spend $25–$35 per person.