It’s simple to fly anonymously. The first method is to remember you have the legal right to go by whatever name you want. The thing about this first method of flying anonymously is you must recruit a friend or family member to help you. Since 9/11, airlines require you to show identification to fly. The exception is when you have someone with ID willing to escort you to the airport. The airline allows them to show their identification and to vouch for you. Your friend has to confirm you are whom you say. You make a flight reservation in whatever name you want, take cash and your friend to the airport. When you pay for your ticket, the airline will ask for your ID. You say, “I don’t have it because I lost it”. Your friend volunteers, “I have identification”. Your friend shows identification, confirms you are whom you say, and you get a plane ticket anonymously.
The second method that allows you to fly without showing identification is when making a return flight. This means you buy a round-trip ticket and the airline presumes you have used the first part of your ticket to get to where you are now. You have supposedly flown to Chicago and you are now ready to fly back to Miami. You go to the ticket counter and they ask you for your ID. Tell them your wallet was stolen or you lost it while you were in Chicago and you don’t have ID. Since the airline believes you flew from Miami, you won’t have to show ID because they assume you showed ID when you got on the plane in Miami. They let you fly without showing ID. Remember, this happens all the time. People lose their wallets. You paid for a round-trip ticket from Miami to Chicago and back to make it appear as though you came from Miami and now you are just on your way back. You fly anonymously.
NOTE: It is interesting that a round-trip ticket is often cheaper to buy than a one-way ticket!