The Illinois move is a tax-reset story more than a price story. Chicago-area prices run higher, with the metro median around $375K to $380K, and the statewide median is about $310K, while property taxes are among the highest in the country, commonly cited near 2% of home value. Around Bowling Green, the median sold price runs $302,495 (Paragon MLS, August 2026) and property tax bills usually land well under 1% of value.
The income tax gap is smaller but still real: Illinois holds a flat 4.95%, Kentucky's flat rate is 4% and ratcheting down. Neither state taxes Social Security income, so retirees keep that line even. What changes is everything on the housing side: newer builds, larger lots and acreage at prices that left Illinois years ago.