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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.

2 results matching: Escorted Rail Tours to Chicago

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USA Coast to Coast
(37 reviews)
2020MayJunSepOct
20 days from
£4,395 pp
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20 days from
£4,395
per person
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tour map
  • DestinationUSA
  • Starts / EndsLHR Heathrow
  • AccommodationHotel
  • TransportFlight, Rail
Map and accommodation
The Trans-American Rail Tour
(15 reviews)
2020MayJunSep
2021Oct
19 days from
£4,495 pp
View Details
19 days from
£4,495
per person
View Details
tour map
  • DestinationUSA
  • Starts / EndsLHR Heathrow
  • AccommodationHotel
  • TransportFlight, Rail
Map and accommodation
Our customers love our Chicago tours
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The Trans-American Rail Tour
Mr J Cattigan
“It was exactly what we thought it would be and met all our needs. Travel was good, hotels excellent (apart from Niagara, which didn’t detract from the overall experience). Guide was excellent and what we saw was exceptional.
USA Coast to Coast
Anonymous
“The holiday was well organised from start to finish . I knew from day to day what to expect, info on our day and time and where to meet
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