Chicago’s vibrant entrepreneurial landscape is home to numerous small business owners who have transformed their visions into successful enterprises. Their stories not only highlight individual determination but also underscore the city’s supportive ecosystem for startups and local businesses.
Double Trip Press: Reviving Traditional Craftsmanship
In the Lincoln Square district, Double Trip Press has established a unique letterpress studio that marries traditional printing techniques with modern design. The 1,000-square-foot space, designed by Danielle Beaulieu of Lieu architectural studio, reflects the tactile essence of letterpress printing. Housing a vintage Vandercook press, the studio emphasizes a blend of craftsmanship and thoughtful design, offering a refined environment that honors the analogue roots of the art form. Read more
Babe’s Sports Bar: Championing Women’s Sports
Set to open in Logan Square, Babe’s Sports Bar is part of a national trend of establishments dedicated to women’s sports. Inspired by founder McConnell-Johnson’s experience of struggling to find venues airing the WNBA championship in 2021, Babe’s aims to showcase a variety of women’s sports, from basketball to roller derby. This initiative reflects the growing popularity and viewership of women’s sports, creating a community hub for fans to gather and celebrate female athletes. Learn more
Boxville: Innovative Business Incubation
Boxville, Chicago’s first business incubator built out of shipping containers, has become a community hub in the Bronzeville neighborhood. Founded by Bernard Loyd, Boxville has grown from hosting four businesses to nine, offering a diverse range of services from bike repairs to food vendors. This innovative approach provides a platform for entrepreneurs to establish and grow their businesses, contributing to the revitalization of the South Side. Discover more
Urban Source: Elevating Interior Design
Urban Source, founded by Jennifer Rossignuolo and Rose Tejeda-Navarre, offers unique textiles, wallpapers, and window treatments to the public—items typically available only to trade professionals. With guidance from SCORE counselors, they optimized their showroom and focused on core products, leading to a significant increase in sales. Their success story exemplifies how targeted mentorship and strategic planning can drive business growth. Read their story
Empowerment Through Financial Support
Old National Bank’s Empowerment Small Business Loan Program addresses the need for increased access to capital for small businesses, particularly those owned by minorities and women. Since its launch in 2023, the program has approved $45 million in loans, with 37% assisting Chicago small businesses. This initiative fuels dreams and supports entrepreneurs in achieving their business goals. Learn about the program
These narratives showcase the resilience and innovation of Chicago’s small business community. From preserving traditional crafts to pioneering new business models, these entrepreneurs contribute significantly to the city’s economic vitality and cultural richness.