Old Town Office & Commercial Space
Chicago’s comedy and entertainment district anchored by The Second City, where Wells Street’s boutique retail, historic brownstones, and neighborhood charm create a distinctive urban environment between Gold Coast and Lincoln Park. A compact neighborhood with character, culture, and convenient access to downtown.
Schedule Free Consultation Call (312) 840-9002Old Town: Chicago’s Historic Entertainment District
The Character: Old Town maintains a distinctive identity despite being sandwiched between the Gold Coast and Lincoln Park. The Second City comedy club—which launched the careers of countless comedians from John Belushi to Tina Fey—anchors an entertainment district that includes Zanies Comedy Club and various nightlife venues. Wells Street’s boutique retail corridor and the Old Town Art Fair tradition reflect the neighborhood’s artistic heritage.
Commercial Space Options: Old Town’s compact size limits commercial inventory, but the neighborhood offers boutique office space, neighborhood retail, and restaurant/entertainment space at prices between the Gold Coast premium and Lincoln Park’s more moderate rates. Office rents range from $32-50/SF. Wells Street provides the primary retail corridor with a mix of local boutiques, restaurants, and service businesses. Entertainment venues serve both destination visitors and the affluent residential population.
Why Businesses Choose Old Town: The neighborhood’s convenient location—walking distance to downtown, Gold Coast, and Lincoln Park—appeals to businesses serving multiple adjacent markets. The entertainment district character suits restaurants, bars, and nightlife concepts. Professional services find the neighborhood provides a more intimate scale than downtown while remaining accessible to clients throughout the north side. The affluent residential base supports neighborhood-serving retail and services.
Where Comedy Met Chicago History
Old Town’s history predates the Great Fire of 1871, and some of the neighborhood’s oldest buildings survived that conflagration. The neighborhood developed as a German immigrant community, with St. Michael’s Church—rebuilt after the fire—serving as an anchor. By the 1960s, Old Town had evolved into Chicago’s folk music and comedy scene, with The Second City opening in 1959.
The Second City’s influence on American comedy cannot be overstated. The theater has trained generations of performers and writers who shaped Saturday Night Live, film comedy, and television. This cultural heritage continues to draw visitors and shape the neighborhood’s entertainment-focused commercial character.
Wells Street developed as the neighborhood’s commercial spine, with the annual Old Town Art Fair—one of the nation’s oldest juried art fairs—reflecting the artistic community that once concentrated here. Today the street offers boutique retail, restaurants, and neighborhood services.
The residential population has become increasingly affluent as the neighborhood has gentrified, though Old Town retains more diversity and less exclusivity than the adjacent Gold Coast. Historic brownstones and three-flats mix with newer development, creating varied housing stock and demographics.
Old Town Demographics & Transportation
Understanding the market dynamics of Chicago’s entertainment district
Population & Demographics
Old Town attracts affluent young professionals and empty-nesters who value the neighborhood’s character, walkability, and proximity to downtown and Lincoln Park.
- Resident Population 15,000+
- Median Age 36 years
- Median Household Income $125,000
- Bachelor’s Degree or Higher 78%
- Renter Occupied Housing 55%
- Walk Score 95+
Business & Entertainment Profile
The neighborhood’s entertainment heritage continues with comedy venues, restaurants, and nightlife alongside neighborhood-serving retail and professional services.
- Comedy & Entertainment Venues 10+
- Restaurants & Bars 75+
- Retail Establishments 100+
- Professional Services 50+
- Annual Art Fair Attendance 50,000+
- Second City Shows/Year 600+
Transportation & Accessibility
CTA Brown Line
Sedgwick station nearby. Loop access via elevated.
CTA Red Line
North/Clybourn and Clark/Division stations accessible.
CTA Bus Routes
North (#72), Clark (#22), Sedgwick (#37).
Downtown Access
10 minutes to Loop via LaSalle or Clark.
Walkability
Walk Score 95+. Walking distance to Gold Coast and Lincoln Park.
O’Hare Access
Blue Line from downtown. 45 minutes to terminal.
Parking
Street parking available. Some building garages. $20-35/day.
Biking
Divvy stations throughout. Flat terrain, good infrastructure.
Commercial Property Types in Old Town
Boutique space in Chicago’s historic entertainment district
Professional Office Space
Boutique office space serves professional services, small businesses, and entrepreneurs seeking neighborhood character without downtown formality. Smaller floor plates suit practices requiring 1,000-5,000 SF.
Historic buildings provide character space with exposed brick and vintage details.
Restaurant & Entertainment
The entertainment district character creates opportunities for restaurants, bars, and nightlife venues. Second City and Zanies draw destination visitors who support surrounding dining and drinking establishments.
Restaurant space requires appropriate infrastructure and licensing.
Boutique Retail Space
Wells Street’s retail corridor offers space for boutiques, specialty retail, and neighborhood services. The affluent residential population supports quality retail serving everyday and specialty needs.
Street presence and pedestrian traffic drive retail success.
Medical & Wellness Space
Healthcare practices serving the affluent residential population find appropriate space in Old Town. Dental, dermatology, mental health, and wellness services fit the neighborhood’s demographic profile.
Accessibility and appropriate infrastructure required for medical uses.
Fitness & Wellness Studios
Boutique fitness, yoga, and wellness concepts serve health-conscious residents. The neighborhood supports premium concepts matching its affluent demographic.
Studio spaces require appropriate flooring, ventilation, and utilities.
Creative & Production Space
The neighborhood’s artistic heritage supports creative businesses—design studios, photography, small production spaces. Limited inventory but occasional opportunities in converted spaces.
Character space with flexible layouts suits creative uses.
Old Town Commercial Real Estate Services
Expert tenant representation in Chicago’s entertainment district
Boutique Space Search
Find character space in Old Town’s limited inventory. We search throughout the neighborhood including off-market opportunities and relationship-based transactions.
Restaurant Site Selection
Position your restaurant or entertainment concept near the Second City district. We analyze foot traffic, visibility, and competitive positioning for optimal location selection.
Lease Negotiation
Navigate Old Town’s boutique market with skilled representation. We leverage local market knowledge to achieve favorable terms for neighborhood tenants.
Old Town Commercial Real Estate FAQ
Find Your Old Town Commercial Space
Expert tenant representation in Chicago’s historic entertainment district—at no cost to you.
Schedule Free Consultation Call (312) 840-9002