Charles Bailey may refer to:

• Charles Bailey (medium) (1870–1947), Australian apport medium
• Charles G. Bailey, faculty manager of WMUL, Marshall University
• Charles Justin Bailey (1859–1946), American soldier
• Charles P. Bailey (pilot) (1918–2001), one of the Tuskegee Airmen's most decorated combat fighter pilots
• Charles P. Bailey (surgeon) (1910–1993), American pioneer in heart surgery
• Charles R. Bailey, American Army chaplain
• Charles W. Bailey II (1929–2012), American journalist, newspaper editor and novelist
• Charlie Bailey (American football) (born 1940), American football coach
• Charlie Bailey (footballer) (born 1997), English footballer
• Charlie Collins (musician) née Charlene Bailey, Australian musician

• Charles Baily (1815–1878), English architect and archaeologist
• Charles Bayly (fl. c. 1630–1680), first overseas governor of the Hudson's Bay Company
• Charles Baillie (disambiguation)