| Rivian | Rivian Automotive Inc. | state | 2024 | $827,000,000 | | MEGADEAL  |
| Amazon | Amazon.com | multiple | 2015 | $741,450,000 | | MEGADEAL |
| Rivian Automotive LLC and Rivian, LLC | Rivian Automotive Inc. | state | 2024 | $633,846,750 | | grant |
| Roosevelt/Clark Partners, LLC | | Local | 2019 | $551,200,000 | | Tax Increment Financing |
| Gotion | Volkswagen | multiple | 2023 | $536,000,000 | | MEGADEAL |
| Alloy Property Company, LLC | | Local | 2019 | $487,830,000 | | Tax Increment Financing |
| Calumet City Investors, LLC | | local | 2023 | $426,529,139 | | tax credit/rebate |
| Sears Holdings Corp | Sears | multiple | 2011 | $275,000,000 | | MEGADEAL |
| Diamond-Star Motors (now Mitsubishi Motors) | Mitsubishi Motors | multiple | 1985 | $249,300,000 | | MEGADEAL |
| Sears Roebuck | Sears | multiple | 1989 | $242,000,000 | | MEGADEAL |
| Wieland North America | | state | 2024 | $231,000,000 | | MEGADEAL |
| Gotion, Inc. | Volkswagen | state | 2023 | $213,325,495 | | grant |
| Gotion, Inc. | Volkswagen | state | 2024 | $125,000,000 | | grant |
| Wieland North America, Inc. and its Affiliates | | state | 2024 | $122,441,207 | | grant |
| Motorola Mobility | Lenovo | state | 2011 | $117,900,000 | | MEGADEAL |
| Ford Motor | Ford Motor | multiple | 2000 | $100,900,000 | | MEGADEAL |
| Chicago Lakeside Development, LLC | United States Steel | Local | 2010 | $96,859,748 | | tax increment financing |
| RJR Nabisco (now Mondelez International) | Mondelez International | multiple | 1993 | $90,000,000 | | MEGADEAL (Archived) |
| Open 4 Business LLC | Comcast | state | 2013 | $86,530,196 | | MEGADEAL (Archived) |
| Navistar International | Volkswagen | multiple | 2010 | $84,837,000 | | MEGADEAL (Archived) |
| Amazon | Amazon.com | multiple | 2017 | $83,125,187 | | MEGADEAL (Archived) |
| Goldframe LLC | Meta Platforms Inc. | state | 2021 | $80,000,000 | | tax credit/rebate |
| Board of Trustees of the University of Illinois | University of Illinois | local | 2000 | $75,000,000 | | tax increment financing |
| Rush University Medical Center | Rush University Medical Center | Local | 2008 | $75,000,000 | | tax increment financing |
| Mercy Hospital and Medical Center | | Local | 2005 | $60,897,431 | | tax increment financing |
| Nabisco, Inc. | Mondelez International | Local | 1994 | $60,000,000 | | tax increment financing |
| Boeing | Boeing | multiple | 2001 | $56,000,000 | | MEGADEAL (Archived) |
| Metropolitan Pier and Exposition Authority | | Local | 2014 | $55,000,000 | | tax increment financing |
| Wilson Yard Development I, LLC | | Local | 2004 | $54,228,392 | | tax increment financing |
| Rivian Automotive | Rivian Automotive Inc. | multiple | 2016 | $53,234,013 | | MEGADEAL (Archived) |
| Elk Grove Village Property LLC | | state | 2023 | $51,720,000 | | tax credit/rebate |
| Lion Electric Manufacturing USA Inc. | | state | 2024 | $48,949,064 | | grant |
| Elk Grove Village Investments LLC. | | local | 2023 | $46,919,601 | | tax credit/rebate |
| Digital Realty Trust, LP | Digital Realty Trust | state | 2020 | $40,448,235 | | tax credit/rebate |
| S&C Electric Co., a Delaware corp. | | Local | 2005 | $39,735,000 | | tax increment financing |
| S&C Electric Co., a Delaware corp. | | local | 2018 | $39,735,000 | | tax increment financing |
| Microsoft Corporation | Microsoft | state | 2021 | $38,813,493 | | tax credit/rebate |
| Mercy Hospital and Medical Center | | local | 2018 | $38,000,000 | | tax increment financing |
| Handi-Foil Corporation | | state | 2018 | $35,000,000 | | tax credit/rebate |
| Randolph Tower City Apartments, Inc. | | Local | 2010 | $34,000,000 | | tax increment financing |
| Eport 600 Property Owner L.L.C. | | Local | 2001 | $33,243,085 | | tax increment financing |
| W2005 CMK Realty, L.L.C. | | local | 2006 | $31,587,000 | | tax increment financing |
| SCI | | Local | 2014 | $31,000,000 | | tax increment financing |
| SCI | | local | 2018 | $31,000,000 | | tax increment financing |
| KINGSLAND DEVELOPMENT CORP | | local | 2007 | $30,000,000 | | tax credit/rebate |
| L&M Riverbend Venture | | local | 2008 | $29,500,000 | | tax increment financing |
| River Point LLC | | Local | 2012 | $29,500,000 | | tax increment financing |
| Serverfarm LLC dba SF CH1, LLC | | state | 2023 | $28,500,000 | | tax credit/rebate |
| Aligned Data Centers (EGV) PropCo, LLC | | state | 2023 | $28,500,000 | | tax credit/rebate |
| Digital Realty Trust, LP | Digital Realty Trust | state | 2021 | $28,060,835 | | tax credit/rebate |
| NNT Global Data Centers | | state | 2020 | $27,600,000 | | tax credit/rebate |
| Microsoft Corporation | Microsoft | state | 2021 | $27,500,000 | | tax credit/rebate |
| LaSalle Street Capital, Inc. | Bank of America | local | 2003 | $27,037,699 | | tax increment financing |
| BR Congress Owner, LLC | | local | 2023 | $27,000,000 | | tax increment financing |
| Primestor 119, LLC | | Local | 2005 | $26,600,000 | | tax increment financing |
| W9/MLM R.E. L.P. and W9/MLM Brickyard, L.L.C. | | Local | 2003 | $26,500,000 | | tax increment financing |
| Chirisa Volo LLC | | state | 2023 | $26,200,000 | | tax credit/rebate |
| UAL Corp. and United Airlines, Inc. | United Airlines Holdings | local | 2017 | $25,889,768 | | tax increment financing |
| MEDP Mission Critical Facility, LLC dba Metro Edge | | state | 2023 | $25,712,395 | | tax credit/rebate |
| Aligned Data Centers | | state | 2021 | $25,250,000 | | tax credit/rebate |
| Microsoft Corporation | Microsoft | state | 2020 | $25,200,000 | | tax credit/rebate |
| Rosenwald Courts Apartments LP | | Local | 2012 | $25,000,000 | | tax increment financing |
| STACK Infrastructure | | state | 2020 | $25,000,000 | | tax credit/rebate |
| T5@Chicago II, LLC | | state | 2020 | $25,000,000 | | tax credit/rebate |
| Coresite, L.P. | American Tower Corp. | state | 2020 | $25,000,000 | | tax credit/rebate |
| Quality Technology Service (QTS) | | state | 2021 | $25,000,000 | | tax credit/rebate |
| SDC CHI I, LLC | | state | 2021 | $25,000,000 | | tax credit/rebate |
| CyrusOne (C1 Chicago) | CyrusOne | state | 2022 | $25,000,000 | | tax credit/rebate |
| SDC CHI II Busse, LLC | | state | 2022 | $25,000,000 | | tax credit/rebate |
| EdgeConneX | | state | 2023 | $25,000,000 | | tax credit/rebate |
| UAL Corp. and United Airlines, Inc. | United Airlines Holdings | Local | 2009 | $24,389,768 | | tax increment financing |
| A. Finkl & Sons Co. | Swiss Steel | Local | 2011 | $22,500,000 | | tax increment financing |
| Solo Cup Company | Dart Container | Local | 1999 | $22,090,000 | | tax increment financing |
| Open 4 Business Productions, LLC | Comcast | state | 2022 | $21,031,843 | | tax credit/rebate |
| Loyola University Chicago | | Local | 2005 | $20,400,000 | | tax increment financing |
| Archer Daniels Midland Company | Archer Daniels Midland | state | 2008 | $20,218,274 | | tax credit/rebate |
| CFUJ III Harper Court LLC et al. | | local | 2011 | $20,045,000 | | tax increment financing |
| Harper Court Partners LLC | | Local | 2010 | $20,045,000 | | tax increment financing |
| Sears Holdings Management Corporation | Sears | state | 2016 | $20,013,310 | | tax credit/rebate |
| BR Congress Owner, LLC | | local | 2022 | $20,000,000 | | tax increment financing |
| HRE Crawford LLC | | local | 2019 | $19,671,393 | | property tax abatement |
| Twentieth Century Fox Film Corporation | Walt Disney | state | 2023 | $18,980,791 | | tax credit/rebate |
| Chicago Theater Group | | Local | 1997 | $18,800,000 | | tax increment financing |
| Livent Realty (Chicago) Inc. | | Local | 1996 | $18,399,077 | | tax increment financing |
| Open 4 Business LLC | Comcast | state | 2018 | $18,202,192 | | tax credit/rebate |
| Open 4 Business, LLC | Comcast | state | 2021 | $18,117,892 | | tax credit/rebate |
| Michigan Cermak Indiana LLC | | local | 2016 | $18,035,279 | | property tax abatement |
| Blackstone Hotel Developer LLC and Urban Heritage Chicago Blackstone Hotel LLC | | local | 2005 | $18,000,000 | | tax increment financing |
| Tenaska, Inc. | Tenaska | state | 2009 | $18,000,000 | | grant |
| Sage Hospitality Resources | | Local | 2005 | $18,000,000 | | tax increment financing |
| Evergreen Imagine JV LLC | | local | 2022 | $18,000,000 | | tax increment financing |
| mHUB | | local | 2023 | $17,650,000 | | tax increment financing |
| Palmet Venture, LLC | | Local | 1997 | $17,600,000 | | tax increment financing |
| mHUB | | local | 2023 | $17,550,000 | | tax increment financing |
| Universal Television, LLC | Comcast | state | 2022 | $17,507,503 | | tax credit/rebate |
| Chicago Manufacturing Campus, LLC | | Local | 2001 | $17,183,334 | | tax increment financing |
| Universal Television, LLC | Comcast | state | 2023 | $16,800,653 | | tax credit/rebate |
| Open 4 Business LLC | Comcast | state | 2018 | $16,369,060 | | tax credit/rebate |
| Radfords Run, LLC fka Twin Forks LLC | | state | 2017 | $16,311,607 | | tax credit/rebate |
| Open 4 Business LLC | Comcast | state | 2017 | $16,117,552 | | tax credit/rebate |
| Tennis Corporation of America, Inc. & Columbia Equities, LLC | | local | 2019 | $15,881,730 | | property tax abatement |
