Claim and Claim Adjustment Expense Reserves - Schedule of Net Strengthening or Releasing of Prior Accident Year Reserves (Workers' Compensation) (Detail) - Property and Casualty Operations [Member] - Workers' Compensation [Member] - CNA Financial [Member] - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2018	Dec. 31, 2017	Dec. 31, 2016	Dec. 31, 2015	Dec. 31, 2014	Dec. 31, 2013	Dec. 31, 2012	Dec. 31, 2011	Dec. 31, 2010
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	$ (32)	$ (63)	$ 145
2009 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	1	11	7	$ 5	$ 10	$ 5	$ 2	$ 10	$ 7
Net Strengthening or (Releases) of Prior Accident Year Reserves	58
2010 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(1)	3	20	12	22	22	22	$ 49
Net Strengthening or (Releases) of Prior Accident Year Reserves	149
2011 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(2)		25	(8)	12	6	$ 34
Net Strengthening or (Releases) of Prior Accident Year Reserves	67
2012 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(2)	(5)	9	10	32	$ 26
Net Strengthening or (Releases) of Prior Accident Year Reserves	70
2013 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(11)	(25)	26	20	$ 35
Net Strengthening or (Releases) of Prior Accident Year Reserves	45
2014 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(2)	(27)	(1)	$ 13
Net Strengthening or (Releases) of Prior Accident Year Reserves	(17)
2015 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	2	(25)	9
Net Strengthening or (Releases) of Prior Accident Year Reserves	(14)
2016 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(9)	(21)
Net Strengthening or (Releases) of Prior Accident Year Reserves	(30)
2017 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(8)
Net Strengthening or (Releases) of Prior Accident Year Reserves	(8)
Total net development for the accident years presented above [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	(32)	(89)	95
Adjustment for Development on a Discounted Basis [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves		(3)	(3)
Total net development for the accident years prior to 2009 [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	7	28	$ 53
Unallocated Claim Adjustment Expense Development [Member]
Claims Development [Line Items]
Strengthening or (Releases) of Prior Accident Year Reserves	$ (7)	$ 1