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Discontinued Operations (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2017
Sep. 30, 2017
Jun. 30, 2017
Mar. 31, 2017
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Discontinued Operation, Income (Loss) from Discontinued Operation Disclosures [Abstract]                        
Income Tax Expense                 $ (0.7) $ (0.5) $ (2.2)  
Income from Discontinued Operations $ 1.5 $ (0.1) $ 0.1 $ 0.2 $ 1.0 $ (0.1) $ 0.0 $ 0.1 $ 1.7 $ 1.0 $ 4.1  
Income from Discontinued Operations Per Unrestricted Share:                        
Basic (in dollars per share)                 $ 0.03 $ 0.02 $ 0.08  
Diluted (in dollars per share)                 $ 0.03 $ 0.02 $ 0.08  
Property and Casualty 1,874.9       1,016.8       $ 1,874.9 $ 1,016.8 $ 931.4 $ 862.8
Unitrin Business Insurance [Member]                        
Discontinued Operation, Income (Loss) from Discontinued Operation Disclosures [Abstract]                        
Results of Operations                 2.4 1.5 $ 6.3  
Income from Discontinued Operations Per Unrestricted Share:                        
Property and Casualty $ 27.5       $ 32.8       $ 27.5 $ 32.8