Chicago has emerged as a major hub for middle market investment banking activity in recent years. The city’s central location, large professional talent pool, and proximity to major Midwest corporations have made it an ideal location for boutique investment banks focusing on the middle market. In 2020, middle market M&A deal value in Chicago reached record levels, with several investment banks dominating the league tables. This article will provide an overview of the key Chicago-based middle market investment banks and their major deals closed in 2020.

William Blair tops Chicago middle market investment banking league tables
William Blair is the clear leader when it comes to Chicago middle market investment banking activity. The firm has a strong focus on technology, healthcare, financial services and industrial sectors. In 2020, William Blair advised on over 100 completed middle market M&A transactions worth over $10 billion in total. Some of their marquee deals include advising DailyMail.com on its sale to DMG Media, representing Paylocity in its acquisition of Samepage, and advising Ascend Learning on its sale to Providence Strategic Growth.
Mesirow Financial excels in diversified industrials sector
Mesirow Financial has carved out a strong position in the Chicago middle market through its expertise in diversified industrials. The firm advised on several major manufacturing, distribution and business services deals in 2020, including the sale of Gas Transport Systems to Chart Industries and Gibson Brands’ acquisition of Mesa Boogie. Mesirow focuses on founder-led businesses and corporate divestitures in the $25-250 million range across the upper Midwest.
Harris Williams builds strength in healthcare
Harris Williams has been aggressively expanding its presence in Chicago, driven by the city’s burgeoning healthcare sector. In 2020, the firm advised on 17 healthcare transactions out of its Chicago office. Notable deals include the sales of Option Care Health to BioScrip and Avella Specialty Pharmacy to Kroger. Harris Williams leverages its broader national footprint to connect middle market healthcare companies with strategic acquirers and private equity firms.
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Lincoln International stands out in the technology space through its Enterprise Software and IT Services group. The group completed over 20 deals in 2020, including representing Hyland Software in its acquisition of Alfresco. Lincoln’s Chicago office has been involved in over 275 transactions in the past five years, reflecting the city’s strength in mid-sized tech companies.
Piper Sandler gains momentum in financial services
Piper Sandler has developed deep expertise in financial services, having advised on over 225 transactions in the sector since 2014. The firm made several notable contributions to Chicago’s middle market banking scene in 2020, including advising First Midwest Bancorp on its merger with Old National Bancorp, and assisting CIBC with its acquisition of Cleary Gull. Piper Sandler’s Chicago-based team focuses on M&A deals between $25 million and $250 million in value.
Chicago has cemented itself as a major hub for middle market investment banking, with firms like William Blair, Mesirow Financial, Harris Williams, Lincoln International and Piper Sandler dominating the landscape. The city’s vibrant mid-market M&A ecosystem provides ample opportunities for boutique investment banks to carve out profitable niches and deliver value to clients across the Midwest.