Rent
Neck and neck
Oakland and Madison are about even on rent.
Oakland
$2,150/mo
Madison
$2,150/mo
What this means for your life
Typical rent in Oakland is $2,150 a month versus $2,150 in Madison, close enough that housing cost should not decide the move by itself. Factor it into your budget alongside salary differences between the two markets, then pick the city that wins the categories you actually live in: safety, schools, pay, or weather.