Question: when do the white sox play the cubs
Answer: Chicago Cubs Chicago White Sox First meeting June 16 , 1997 , Comiskey Park ( II ) Latest meeting July 27 , 2017 , Guaranteed Rate Field Next meeting May 11 , 2018 , Wrigley Field Statistics Meetings total 112 Most wins White Sox , 58 Regular season series 58 -- 54 , White Sox Largest victory 12 -- 2 , White Sox ( June 24 , 2005 ) Longest win streak Cubs : 6 ( June 22 , 2007 -- June 22 , 2008 ) White Sox : 5 ( June 27 , 2009 -- June 12 , 2010 ) Current win streak Cubs : 3 Post-season history 1906 World Series : White Sox , 4 -- 2