Old Town Historic District
Free
Historic TownHistoryLocal LifePhoto Spot
Overview
The Old Town Historic District is a charming, tree-lined neighborhood that captures a distinct, old-world European romance within modern Chicago. Renowned for its beautifully preserved Victorian-era architecture, brick-paved alleys, and historic gas lamps, the area feels completely removed from the nearby skyscraper rush. Strolling along Wells Street reveals an eclectic collection of artisanal coffee shops, legendary comedy clubs like The Second City, and cozy bistros, offering a wonderful taste of vintage artistic neighborhood character.
Practical Info
Suggested DurationAbout 1.5-2.5 hours
Best TimeWeekend mornings through afternoons from May to October are perfect for an architectural stroll. Locals decorate windows with flowers, and walking along Wells Street reveals beautifully preserved 19th-century Victorian brick buildings. It pairs nicely with brunch at a local vintage cafe.
Getting ThereTake the 'L' Brown or Purple Lines from downtown to the Sedgwick station. Upon exiting, walk east for approximately 3 minutes to enter the heart of the historic landmark district.
Travel Tips
- On weekends and Friday evenings, Wells Street's famous bars and comedy clubs (like The Second City) draw massive crowds. Street parking becomes impossible and is mostly restricted to local permits. Take the CTA Brown Line to Sedgwick instead.
- If planning a downstream trip to the iconic Second City comedy club, buy tickets online weeks in advance. Walk-ups are rarely available, and there is a mandatory one-drink minimum purchase inside the theater.
Photo Tips
Photo Rules
- When photographing the signature 19th-century Victorian brick buildings along Crilly Court, stay strictly on public sidewalks. Private stoops and front yards are strictly off-limits; trespassing will trigger resident complaints.
Reviews
Positive
- The streets are lined with a wealth of gorgeous late 19th-century Victorian brick homes; its architectural depth and visual charm are fully real.
- This is the legendary birthplace of The Second City comedy troupe; its cultural history is rich, filled with indie theaters and vintage shops.
- Transit is highly convenient via the CTA Brown Line directly to the heart of the district; walking its tree-lined streets feels wonderfully serene.
- Directional signs are very clear; the area is dotted with charming sidewalk cafes and upscale restaurants, maintaining great order and safety.
Heads up
- With recent gentrification, some traditional independent shops have been replaced by generic corporate chains, diluting the raw historic vibe.
- During weekend evenings or the Old Town Art Fair, tourist density spikes on the main strips, making it noisy, packed, and parking a total nightmare.
- As an upscale historic enclave, the local dining and craft bar pricing is generally premium, incurring high costs for secondary spending.
- Some century-old, narrow brick sidewalks are uneven and bumpy, making accessible walking bumpy for wheelchairs or strollers.