Lake Forest stands out for its high incomes, historic estates, and easy access to Lake Michigan and downtown Chicago. Published on March 23, 2026 Senior couple walking in a neighborhood. Credit: Connect Images/Getty Images While the East Coast and the West are known for their high cost of living and affluent retirement communities , the Midwest also offers plenty of wealthy towns to enjoy your golden years. Set on the north shore of Lake Michigan, Lake Forest, Illinois, has been named the richest retirement town in the Midwest by GOBankingRates . The historic Chicago suburb, located about 30 miles north of the city, places No. 2 in the nationwide ranking, only behind Saratoga, California. For this 2026 study, GOBankingRates considered cities with populations of 15,000 in which at least 25 percent of the population was aged 65 and older. Lake Forest’s median household income is $235,081, while its livability score is 67 out of 100.…