Route 66 - Chicago Illinois

Welcome to Chicago, Illinois Richard, the third largest city in the United States of America, and a trading post since the late 17th century. The first permanent resident was a free Haitian man, Jean Baptiste Point du Sable - little is known of him before he first appears in Chicago in the 1770s, but he was certainly resident there from 1790 and is known as the founder of the city. By the time Mark Twain said "she outgrows [a man's] prophecies faster than he can make them" in 1883, Chicago had gone from trading post on the river to thriving town.

When the Willis Tower - formerly known as the Sears Tower - was completed in 1973, it was the tallest building in the world, and remained so for 25 years. Although still impressive, the tower is only the second tallest in the States, and has slumped to 14th in the world. It gets its original name from Sears Roebuck, who at the time of construction required a staggering 3,000,000 square feet of office space for its employees.

After 40 years, Sears' naming rights bizarrely expired, and in March 2009, Willis Group Holdings not only leased part of the building but obtained naming rights too. Potentially, the name could change again in 2024, when rights become available again, although the Chicago Tribune notes that "we're stubborn about such things", and that the current name hasn't yet stuck in the mind of locals, let alone the world.

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