Douglas Antonio

Douglas J. AntonioPartner

  • Chicago: (312) 704-2198
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Douglas J. Antonio is one of Chicago’s most highly regarded attorneys for his work on real estate transactions financed through federal, state and local government programs.  His years of experience in working with these programs allows Doug to bring a unique perspective to his client’s transactions and to develop creative solutions that help them close even the most difficult transactions.  His clients include developers, syndicators and investors in commercial and residential real estate and affordable housing and community development projects.


American Bar Association
Illinois State Bar Association



Selected by peers as a Leading Lawyer in :  Public Finance; Commercial Real Estate, Real Estate Finance and Business Tax (2001-2017)

Selected for inclusion in Illinois Super Lawyers (2005-2016)

Martindale-Hubble AV rated (1992-2015), 5.0/5.0 Overall Client Rating –

Top Commercial Real Estate Lawyer, Mid-West Real Estate News (2005)

American Jurisprudence Award in Decedants, Estates and Trusts

Beta Gamma Sigma, Business Honors Fraternity

Omicron Delta Epsilon, Economics Honors Fraternity

Pi Mu Epsilon, Mathematics Honors Fraternity


Civic & Professional

  • Real Estate Investment Association
  • Adjunct Professor, The John Marshall Law School, Affordable Housing, 1999-2003; Partnership Taxation, 1996-97
  • Illinois Chairman, Earned Income Tax Credit Outreach Program, American Bar Association
  • American Bar Association, Sections of Taxation (Partnership and Real Estate Committees); Business Law Section; Real Property, Probate and Trust Law; and Forum on Affordable Housing and Community Development Law
  • Chicago Bar Association, Federal Taxation Committee, Executive Committee (2000-present); Chair (1999-2000);  Vice Chair (1998-1999); Secretary (1997-1998)
  • Chicago Bar Association, Partnerships, Real Estate and other Tax Shelter Investments, Chair (1992-1994) 
  • Chicago Bar Association, Ad-Hoc Committee on the Partnership Anti-Abuse Regulation, Chair (1994-1996), Principal Author of the CBA's comments to the following Regulations: (1) Treasury Regulation §1.1001-2; (2) Treasury Regulation §1.707-3 through -6; (3) Treasury Regulation §1.704(c); and (4) Treasury Regulation §1.701-2.

Douglas J. Antonio's recent or notable engagements and experience includes:

  • Represented developer in connection with 100 unit HUD assisted project in Chicago, Illinois.  Devised a plan to allow the acquisition and rehabilitation using bond financing, Illinois Affordable Housing Tax Credits, Low Income Housing Tax Credits and other assistance; helped client stave off likely loss of the purchase to another party.
  • Represented developer of 240 unit HUD assisted project in Park City, Illinois; made client aware of financing source ultimately used to fund the project;  brought in competing investors so that the client could maximize the credit yield;  closed one of the only HUD insure-upon-completion loans in the Chicago office.
  • Represented client in the acquisition, rehabilitation and syndication of a HUD subsidized scattered site apartment project using bonds, low-income housing tax credits, TIF proceeds, HOME grants, Illinois Affordable Housing Tax Credits and FHA insurance; devised a creative way to satisfy the 50% test to assure the project qualified for tax credits.
  • Provided tax opinion for large New Markets Tax Credit Project in Chicago, Illinois.
  • Represented developer with successful bid for purchase and the ultimate syndication of Low Income Housing Tax Credits and Historic Tax Credits, Section 8 and FHA insurance under 221(d)(4) for a 628 unit housing project in Chicago, Illinois.
  • Assisted client through successful litigation with HUD to ultimately acquire, rehabilitate and syndicate a 357 unit project in Chicago, Illinois using Low Income Housing Tax Credits.
  • Represented developer in all aspects of structuring, acquisition, rehabilitation and syndication of 147 unit project from the Chicago Housing Authority.
  • Represented client in developing a structure for utilizing insurance proceeds from a major fire and used a bankruptcy proceeding to allow the client to acquire, rehabilitate and finance a 458 unit apartment complex in Chicago, Illinois.