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Escorted Rail Tours to Chicago

Discover Illinois' Windy City

Set on the shores of the vast Lake Michigan, the 'Windy City' of Chicago is the capital of the state of Illinois. The area was first settled by Europeans in the early 19th century, though by 1830 it still had a population of just fifty. However, it was able to develop as a centre for trade with the more established East Coast cities; when the railway reached it in 1848, Chicago soon became the largest railway hub in the world. By 1900, the city was home to more than two million people, and it is now the third most populous city in the USA.

Today, Chicago boasts a magnificent skyline along with many highly-rated museums, restaurants and cafés. Naturally for such a large city, there are a range of diverse activities to be enjoyed here. The 110-storey Willis Tower was the world's tallest building on its completion in 1974, and has a great observation deck for views over, on a clear day, four states - Illinois, Michigan, Wisconsin and Indiana.

The nearby Hancock Centre also offers fantastic views of Chicago, with some excellent refreshment facilities at the top. Millennium Park, with its interesting sculptures, is also worth a visit. Boat trips (with guided commentary) are available, with themed trips including an "Architecture of Chicago" tour. The 'Magnificent Mile' of North Michigan Avenue offers excellent shopping opportunities, and nobody should leave Chicago without taking a ride on the "Loop" - Chicago's famous and iconic overhead metro.

We’ve found 6 tours for you matching: Escorted Rail Tours to Chicago

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USA Coast to CoastUSA Coast to Coast

USA Coast to Coast

Experience a once-in-a-lifetime coast to coast rail journey across the most diverse country in the world! Your photo album will include many of America's highlights including the Statue of Liberty, the White House, the Wild West, the Rockies, the Grand Canyon, Hollywood Boulevard and the Golden Gate Bridge.

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2018AugSepOct
2019AprMayJunAugSepOct

20 days from £3,995 pp

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The Trans-American Rail TourThe Trans-American Rail Tour

The Trans-American Rail Tour

Wake up in the city that never sleeps at the end of this epic adventure. This once in a lifetime journey takes you to some of America's most famous sights including Alcatraz, the Las Vegas strip, the Grand Canyon and Niagara Falls, and travels on some spectacular railroad excursions, including the Grand Canyon Railroad.

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2018AugSepOct
2019AprMayJunJulAugSep

19 days from £4,395 pp

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Save up to £200 pp
Premium USA Coast to CoastPremium USA Coast to Coast

Premium USA Coast to Coast

Experience the USA in style on this enhanced version of our successful USA Coast to Coast tour, staying in many unique hotels entangled with key moments in American history. Take in the Rockies by rail, enjoy a dinner cruise around the San Francisco Bay and view the Grand Canyon on a heritage rail journey.

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2018Sep
2019MayAugSep

20 days from £6,795 pp

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Save up to £100 pp
White House, Washington D.C.White House, Washington D.C.

American Rail Adventure

Explore the USA from New York to San Francisco, on a 15-day Stateside adventure by rail. Travel on iconic Amtrak trains and visit incredible American cities en-route, from bustling Washington D.C. to Chicago, Denver and Salt Lake City, for a comprehensive tour of the United States.

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2019AprJunSep

15 days from £3,195 pp

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Mississippi Cruise & Chicago Blues

Travel from New Orleans Chicago, following the route of the 'Blues Highway' by traditional steamboat and Amtrak rail, on a two-week tour packed with Southern charm, historic towns and the Memphis' musical legacy, from Graceland to Sun Studio and Beale Street.

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Around the World in 50 Days

Beginning and ending in London, we travel just under 23,000 miles across the globe on this incredible worldwide adventure. Starting in the iconic 'Big Apple', we chart a course across the heartland of America, to the West Coast. From there, we cross the Pacific into Asia and immerse ourselves in the rich legacies of China, before boarding the iconic Tsar's Gold Train for the journey across Russia. For the final leg of the journey, we head into central Europe, south through the imperial cities to Venice, boarding the luxurious Simplon-Orient- Express for the journey home.

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