Every Route 66 adventure begins in Chicago, where history and modern energy meet. Known as the birthplace of the skyscraper, the city offers multiple ways to experience its impressive skyline. Begin your city exploration with the Chicago Architecture Center’s River cruise aboard Chicago’s First Lady for an interesting, narrated tour of the buildings along the way.
Take your pick from one of the many museums in the city, stroll down the iconic shopping district of The Magnificent Mile 360 or wander through Millenium Park and see ‘The Bean’ for a reflective view of the city skyline. For an elevated jaw-dropping view, Skydeck Chicago and 360 CHICAGO observation decks offer day and night-time timed visits.
There will be plenty of dining choices in the city, including the popular Italian beef sandwich and the classic Chicago pizza!