How did freedom change between the Gilded Age and the 1920s?
I would argue that the conception of freedom in the Gilded Age was more of a concept of economic freedom. By the time the '20s came around, freedom was defined more in terms of personal choices.
The Gilded Age was an era of laissez-faire capitalism. It was also an era in which only the rich had a great deal of freedom. The rest of the people did not have as much freedom because they did not have enough money. Therefore, their lives were circumscribed by the need to work. During this time, freedom was seen as the freedom to compete economically. The "robber barons" were the ones who won this competition.
By the '20s, there was a much larger middle class than there had been. This middle class had the money and the time to do things for fun. Because of this, freedom came to be defined in terms of personal choices. Freedom now was the freedom to go to a speakeasy or to wear the clothes of a flapper. There was still laissez-faire to a great degree, but the common idea of freedom was more of a personal freedom as opposed to an economic type of freedom.
So, the major difference is that freedom in the Gilded Age was economic freedom and freedom in the '20s was personal freedom.