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Discontinued Operations (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Discontinued Operation, Income (Loss) from Discontinued Operation Disclosures [Abstract]                        
Income Tax Expense                 $ (2.2) $ (3.1) $ (1.1)  
Income from Discontinued Operations $ 2.1 $ 2.0 $ (0.1) $ 0.1 $ 3.3 $ (0.1) $ 2.3 $ 0.0 $ 4.1 $ 5.5 $ 1.9  
Income from Discontinued Operations Per Unrestricted Share:                        
Basic (in dollars per share)                 $ 0.08 $ 0.10 $ 0.04  
Diluted (in dollars per share)                 $ 0.08 $ 0.10 $ 0.04  
Property and Casualty 931.4       862.8       $ 931.4 $ 862.8 $ 733.9 $ 843.5
Unitrin Business Insurance [Member]                        
Discontinued Operation, Income (Loss) from Discontinued Operation Disclosures [Abstract]                        
Results of Operations                 6.3 8.6 $ 3.0  
Income from Discontinued Operations Per Unrestricted Share:                        
Property and Casualty $ 38.3       $ 50.3       $ 38.3 $ 50.3