Karen A. Hayes


[email protected]

Phone: (312) 360-6545

Fax: (312) 360-6520



Karen Hayes is a Partner in the Corporate Practice Group who advises clients federal income tax matters. Karen represents corporations, partnerships and private equity funds involved in a variety of taxable and non-taxable transactions, domestic and cross-border mergers and acquisitions, divestitures, investments, reorganizations, partnerships and joint ventures.

In addition, Karen has represented tax credit syndicators, banks and other institutional investors with respect to investments in affordable housing projects that generate low-income housing tax credits under Section 42 of the Internal Revenue Code. Karen also has experience advising real estate investment trusts (REITs) with respect to tax matters.

In 2016, Karen was recommended by The Legal 500 in the area of non-contentious tax. Prior to joining Freeborn, Karen was a Partner at Sidley Austin LLP. 


  • Represented a U.S. multinational company in its sale of a business division to a non-U.S. buyer in a transaction valued at $5.4 billion
  • Represented a Boston-based private equity firm in multiple investments and acquisitions, including the recent acquisition of a large online media company
  • Represented a Midwest-based private equity firm and its portfolio companies in numerous acquisitions and sale transactions, including the recent acquisition of a technology solutions provider and the acquisition by a U.S. portfolio company of a Canada-based business
  • Represented a large U.S. multinational company in its sale of a business division to a New-York based private equity firm

Honors & Awards

Honors & Awards

  • The Legal 500, Non-Contentious Tax, 2016
  • Illinois Leading Lawyers - Emerging Lawyers - 2020

Professional Activities

Professional Activities

  • Member, American Bar Association, Taxation Section
  • Former chair, Corporations (Business) Taxation Division of the Federal Tax Committee of the Chicago Bar Association, 2010 - 2012

Speaking Engagements

  • "Ethical Issues for Tax Professionals," Tax Executives Institute State and Local Tax Seminar, Chicago (March 2018)
  • "Tricks and Traps with Acquisition/Rehab Transactions" — American Bar Association Forum on Affordable Housing and Community Development Law (May 23, 2014).