5-Day Route 66, Chicago Mafia, Harley-Davidson Museum, Michigan Avenue, Hemingway House Tour from Chicago

On the designated pick-up area

Holiday Inn Express Chicago-Schaumburg or similar

U.S. Route 66 (US 66 or Route 66) nicknamed the Mother Road, was one of the original highways within the U.S. Highway System. The highway began from Chicago and ran all the way to Santa Monica, California, covering a total of 2,448 miles (3,940 km).

We will first visit the crossing of Adams Street and Michigan Avenue, which is the starting point of Route 66. Then we will have breakfast at Lou Mitchell’s, also known as "the first stop on the Mother Road.". The restaurant has kept its original decoration since 1949 so you can feel Route 66’s classic golden age.

We will then stop at Joliet and visit the Old Joliet Prison Park where the famous TV series Prison Break was made. Afterwards, we will visit Pontiac, another important destination on Route 66. We will have a guided museum tour through which you can have a comprehensive understanding of the Mother Road. The tour will be guided by the city staff and includes Route 66 Hall of Fame (the largest collection of Route 66 Memorabilia in Illinois), the Pontiac Oakland Automobile Museum (one of the world’s greatest and most expansive collection of Pontiac) and the Museum of the Gilding Arts (store signs on Route 66 used to be made of gold! Here you can also learn how to make gold leaf).

We will go back to Chicago in the evening.

On the designated pick-up area

Holiday Inn Express Chicago-Schaumburg similar

This tour will show you the best of Chicago in one day. This is a world’s top architecture city with bold architectures. You will take a walk in the Millennium Park, a combination of stunning architecture, sculpture and landscape design located in the heart of downtown Chicago; you will see Cloud Gate, the impressive signature urban sculpture and one of the best public spaces that you can find on earth. Take a break at the Clarence Buckingham Memorial Fountain, one of the world's largest artificial fountains.

Stroll around the Navy Pier, the former Navy training center, which is the most visited lakeshore park in central United States now. You will also take an exclusive tour of the Chicago Theatre, an exquisite French Baroque style theatre. Another stop is Michigan Avenue, the Magnificent Mile, where the Art Institute of Chicago, Grant Park, the historical Chicago Water Tower, shopping malls and boutique stores are located.

To have the best view of this famous city, you will go up to the 360 CHICAGO which soars 1,000 feet above Lake Michigan and the city’s majestic skyline to offer the most breathtaking views of downtown Chicago, the lakefront and four neighboring states: Illinois, Indiana, Michigan, and Wisconsin. It newly presents an enclosed,
glass and steel moveable platform that tilts outward 304 meter above the Magnificent Mile and safely holds up to eight visitors at a time, which will be another thrilling experience for whom like to challenge themselves. As the birthplace of skyscrapers, Chicago has a skyline bristling with skyscrapers. Chicago River flows backwards from Lake Michigan and is lined up with best architecture in town: the corncob shaped Marina City buildings, Trump Tower, Willis Tower and etc. Take our river cruise to enjoy the beautiful urban view of Chicago that goes through the core of city. (The cruise will be closed in winter)

On the designated pick-up area

Holiday Inn Express Chicago-Schaumburg or similar

We will start in the morning towards Milwaukee, the largest city of Wisconsin State, a state where you get to see true American spirit. Milwaukee is the birthplace of Haley-Davidson motorcycles. We will first visit the Harley Davidson Museum that showcases the American legendary motorcycle brand by collection of 450 motorcycles and artifacts including the oldest known Harley Davidson motorcycle. Every handcrafted bike is passing the message of Harley Davidson spirit: passion, freedom, bravery, and individuality.

We will then visit the historical brewery of the Miller Brewing Company, another pride of Wisconsin. As you might have tried the famous Miller brand beers many times, now you can see where they come from. This historical brand also has 155 years of history and interesting facts to share, which will definitely add a kick to your beer when you drink it next time. More importantly, you will end every tour with their famous ice-cold beer samples! Relax and enjoy your brew in the Bavarian-style Miller Inn or outdoor Beer Garden (seasonally) with friends and family at this historic Milwaukee landmark.

After lunch, we will go towards Lake Geneva, a favorite resort city for Chicagoans. Originally called “Big Foot” by the Indians, the area became a popular summer retreat with railroad access from Chicago for the barons of wealth in lumber, cattle, oil, steel, cement, manufacturing, and durable goods (e.g., Morton Salt, Wrigley Chewing Gum), with mansions and large homes such as Stone Manor and Black Point built on the lake from the 1850s, through the heyday of the Roaring, and up to the present day. We will take a walk alongside the lake and take the popular Geneva Lake cruise (Cruise will be closed in winter) to enjoy the narrated highlights of many of the elegant, historic estates as you travel around the eastern end of the lake known as “Geneva Bay” in approximately one-hour.

On the designated pick-up area

In the morning, we will leave for a famous Chicago prohibition bus tour. Guided bus tour will educate you on the full history of prohibition in 1920s and hear about American gangster who attains fame on prohibition era-- Al Capone. We will be visiting the "dark side of Chicago city", where the gangster under Al Capone was active. On the trip, we will go back to the 20s and tasting intriguing cocktail made by professional bartenders in a famous bar where Al- Caroline was back on time.

After lunch, we will visit the majestic estate and ten-acre garden of late Cole-Robert R McCormick, former publisher and editor of Chicago Tribune. The new paper is the Most-read daily newspaper of the Chicago metropolitan area and the Great Lakes region.

Our visit, a guided tour, will explore how Colonel McCormick lived here with his family from 1936-1955, and you will be immersed in McCormick's legacy of journalism, history, architecture, politics, first amendment issues patriotism and philanthropy. *If you are not attending the Mafia Tours, you may choose Chicago University Walking tour instead.