Businessman Willie Wilson running for Chicago mayor for 4th timeBusinessman Willie Wilson announced he is joining the 2027 Chicago mayoral election race, marking his fourth bid for Chicago mayor. Businessman Willie Wilson announced he is joining the 2027 Chicago mayoral election race, marking his fourth bid for Chicago mayor. Businessman Willie Wilson announced he is joining the 2027 Chicago mayoral election race, marking his fourth bid for Chicago mayor. Businessman Willie Wilson announced he is joining the 2027 Chicago mayoral election race, marking his fourth bid for Chicago mayor. CHICAGO (WLS) -- Chicago businessman Willie Wilson is running for mayor, ABC7 learned Wednesday.