The educational philosopher John Dewey is often mentioned as an inspirational figure of the P4C movement. The educational principles that Dewey set-up supports philosophy with children as it was applied later in the educational movement that was led by Matthew Lipman, Ann Margaret Sharp and their predecessors. In Korczak’s ideas and work, as well as in Dewey’s, there appears to be theoretical foundations for philosophy with children. However, a close analysis reveals that philosophizing with children in Korczak’s style is different from the Deweyan way and objectives. In the paper I will present the concept of Philosophy with children as it has been brought forward in Dewey’s writings, and as it is has been brought forward in Korczak’s writings, and I will compare between the two. I would like to suggest that these two different philosophical ideas offer distinctive approaches that may be beneficial for anyone who is interested in philosophical dialogues with children, for clarity and accuracy.