25MAR202022593550 April 9, 2020 Dear Stockholder: On behalf of our Board of Directors, we are pleased to invite you to the 2020 Annual Meeting of Stockholders (the ‘‘Annual Meeting’’) of United Airlines Holdings, Inc. (the ‘‘Company’’ or ‘‘United’’) to be held on May 20, 2020. A notice of the Annual Meeting and proxy statement follows. Please read the enclosed information and our 2019 Annual Report carefully before voting your proxy. In light of the coronavirus (‘‘COVID-19’’) pandemic, for the safety of all of our people, including our stockholders, and taking into account recent federal, state and local guidance that has been issued, we have determined that the 2020 Annual Meeting will be held in a virtual meeting format only, via the Internet, with no physical in-person meeting. At our virtual Annual Meeting, stockholders will be able to attend, vote and submit questions by visiting www.virtualshareholdermeeting.com/UAL2020. Your vote is important. Even if you plan to attend the virtual Annual Meeting, please authorize your proxy or direct your vote by following the instructions on each of your voting options described in the proxy statement. You may vote your shares by Internet, telephone or mail pursuant to the instructions included on the proxy card or voting instruction card. We encourage you to use the first option and vote by Internet. Thank you for your continued support of United. Sincerely, 28APR201620292684 Oscar Munoz Chief Executive Officer 25MAR202022593550 Notice of 2020 Annual Meeting of Stockholders Date and Time Proxy Voting Wednesday, May 20, 2020 Even if you plan to attend the virtual Annual 9:00 a.m., Central Time Meeting, please authorize your proxy or direct your vote as promptly as possible. You may vote your Location shares by Internet, telephone or mail pursuant to the instructions included on the proxy card or Our Annual Meeting can be accessed virtually at: voting instruction card. The Notice of Internet www.virtualshareholdermeeting.com/UAL2020 Availability of Proxy Materials includes instructions for voting over the Internet and requesting a paper Record Date copy of the proxy materials and proxy card. If you attend the Annual Meeting virtually and want to April 1, 2020 revoke your proxy, you may do so as described in the attached proxy statement and vote during the At the meeting, stockholders will be asked to: Annual Meeting on all matters properly brought before the Annual Meeting. 1 Elect the directors named in this proxy statement. You can find detailed information about voting in the section entitled ‘‘General Information About the Ratify the appointment of Ernst & Young LLP Annual Meeting’’ in the attached proxy statement. 2 as the Company’s independent registered public accounting firm for 2020. Consider an advisory vote to approve the 3 compensation of the Company’s named executive officers. Act on three stockholder proposals, if 4 properly presented before the meeting. Act on any other matters that may be 5 properly brought before the meeting. 22APR201522025321 29MAR202005372995 Jennifer L. Kraft Important Notice Regarding the Internet Vice President and Secretary Availability of Proxy Materials for the Annual Chicago, Illinois Meeting of Stockholders to be Held on May 20, April 9, 2020 2020. The Company’s Notice of Annual Meeting, Proxy Statement and 2019 Annual Report to Stockholders are available on the Internet at www.proxyvote.com. Table of Contents Page Page Proxy Statement Summary ............. 1 2019 CEO Pay Ratio ................. 79 Proposal No. 1: Election of Directors ......6 2019 Director Compensation ........... 81 Director Qualifications ................ 6 Cash Retainers for Board and Committee Directors to be Elected by the Holders of Service ........................ 83 Common Stock ................... 7 Equity Compensation ................ 83 Directors to be Elected by the Holders of Non-Executive Chairman Compensation .... 83 Other Classes of Stock .............. 14 Director Compensation Deferral Under the Corporate Governance ................ 16 DEIP ......................... 84 Corporate Governance Guidelines ......... 16 Stock Ownership Guidelines ........... 84 Bylaws, Committee Charters and Other Travel Benefits ..................... 84 Policies ......................... 17 Charitable Contributions .............. 84 Prohibition on Hedging and Pledging ....... 18Audit Committee Report ............. 85 Director Independence ................ 18 Proposal No. 2: Ratification of the Majority Voting; Resignation Policy ......... 19 Appointment of Ernst & Young LLP as Board Meetings ..................... 19 the Company’s Independent Registered Executive Sessions of Non-Management Public Accounting Firm for the Fiscal Directors ....................... 20Year Ending December 31, 2020 ...... 87 Board Leadership Structure ............. 20 Independent Registered Public Accountants . 87 Board Oversight of Risk Management ...... 20 Audit Committee Pre-Approval Policy and Communications with the Board .......... 22 Procedures ..................... 87 Code of Ethics and Business Conduct ...... 22 Independent Registered Public Accounting Environmental Sustainability ............. 22 Firm Fees ...................... 88 Community Engagement ............... 23 Ratification of the Appointment of the Nominations for Directors .............. 24 Independent Registered Public Accounting Committees of the Board .............. 26 Firm .......................... 88 Compensation Committee Interlocks and Proposal No. 3: Advisory Vote to Approve Insider Participation ................. 29 the Compensation of the Company’s Certain Relationships and Related Transactions . 30 Named Executive Officers ........... 90 Beneficial Ownership of Securities ........ 32 Proposal No. 4: Stockholder Proposal Certain Beneficial Owners .............. 32 Regarding Stockholder Action by Directors and Executive Officers .......... 34Written Consent .................. 93 Equity Compensation Plan Information ...... 35 Statement in Opposition to Stockholder Executive Compensation ...............36 Proposal ....................... 94 Compensation Discussion and Analysis ...... 36 Proposal No. 5: Stockholder Proposal Named Executive Officers ............ 37 Regarding a Report on Lobbying Executive Summary ................. 37Spending ....................... 96 Tight Linkage between Performance and Statement in Opposition to Stockholder Executive Pay ................... 40 Proposal ....................... 97 Our 2019 Executive Compensation Proposal No. 6: Stockholder Proposal Governance Practices .............. 42 Regarding a Report on Global Warming- Philosophy and Objectives of Our 2019 Related Lobbying Activities .......... 99 Executive Compensation Program ...... 44 Statement in Opposition to Stockholder Compensation Process and Oversight ..... 45 Proposal ....................... 100 2019 Compensation Components ....... 48 General Information About the Annual Other Compensation Components ....... 56Meeting ........................ 102 Other Executive Compensation Matters . 57 Submission of Stockholder Proposals for Compensation Committee Report ......... 58the 2021 Annual Meeting ............ 108 2019 Summary Compensation Table ....... 58Householding ...................... 108 Grants of Plan-Based Awards for 2019 ...... 61Annual Report ..................... 108 Narrative to 2019 Summary Compensation Other Business ..................... 109 Table and Grants of Plan-Based Awards for Appendix A: Reconciliation of GAAP to 2019 Table ...................... 62Non-GAAP Financial Measures ........ A-1 Outstanding Equity Awards at 2019 Fiscal Year-End ........................ 64 Option Exercises and Stock Vested for 2019 . 66 2019 Pension Benefits Table ............. 67 Narrative to Pension Benefits Table ........ 68 Potential Payments upon Termination or Change in Control ................. 70 Proxy Statement Summary This summary highlights certain information contained elsewhere in this proxy statement. This summary does not contain all of the information that you should consider, and you should read this proxy statement and our 2019 Annual Report carefully before voting. This proxy statement and the accompanying proxy card are being made available to you on approximately April 9, 2020. 2020 Annual Meeting of Stockholders Information Date and Time: Wednesday, May 20, 2020, at 9:00 a.m., Central Time Location*: Our Annual Meeting can be accessed virtually via the Internet at: www.virtualshareholdermeeting.com/UAL2020 To participate in the virtual Annual Meeting, you will need the control number provided on your proxy card, voting instruction form or Notice of Internet Availability of Proxy Materials. If you are not a stockholder or do not have a control number, you may still access the meeting as a guest, but you will not be able to submit questions or vote at the meeting. Record Date: April 1, 2020 * In light of the coronavirus (‘‘COVID-19’’) pandemic, for the safety of all of our people, including our stockholders, and taking into account recent federal, state and local guidance that has been issued, we have determined that the 2020 Annual Meeting will be held in a virtual meeting format only, via the Internet, with no physical in-person meeting. At our virtual Annual Meeting, stockholders will be able to attend, vote and submit questions. Whether or not you plan to attend the virtual Annual Meeting, we urge you to vote and submit your proxy in advance of the meeting by one of the methods described in these proxy