Chicago

Chicago Escorted Tours

Chicago is a popular stop on our Deep South escorted tours. Combining the city’s sporting venues and hearty cuisine with New Orleans’ jazz clubs and Kentucky’s rich bourbon, we’ve selected escorted tours that immerse you in the vibrant spirit of this fabulous region.

Katie Guy
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Chicago to the Golden Gate

  • Chicago
  • Yellowstone National Park
  • Salt Lake City
  • Bryce Canyon National Park
  • Las Vegas
  • Los Angeles
  • Santa Barbara
  • San Francisco
Escorted Tours
2027 Departure Dates Available

An incredible escorted tour as you travel across the country through eight states with a fantastic mix of cityscapes, rural towns and majestic wonders. From Chicago to San Francisco, you’ll travel along the iconic Route 66 to see Mount Rushmore, Yellowstone National Park and Grand Canyon to name a few extraordinary highlights.

14 nights From £3,719 pp Including Flights
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The Great American Crossing

  • New York
  • Washington D.C.
  • Niagara Falls
  • Chicago
  • Yellowstone National Park
  • Salt Lake City
  • Bryce Canyon National Park
  • Las Vegas
  • Los Angeles
  • Santa Barbara
  • San Francisco
Escorted Tours
2027 Departure Dates Available

From New York City to Los Angeles, this classic American tour stops off at some of the most dramatic and exciting places en route - from Niagara Falls to Chicago and the Grand Canyon to Las Vegas.

16 Nights From £3,299 pp Including Flights
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Centennial Historic Route 66

  • Chicago
  • St. Louis
  • Springfield
  • Oklahoma City
  • Amarillo
  • Albuquerque
  • Holbrook
  • Page
  • Grand Canyon
  • Las Vegas
  • Los Angeles
Escorted Tours
2027 Departure Dates Available

Celebrate the Route 66 centennial on this premier escorted tour from the skyscrapers of Chicago to the shores of Santa Monica. This historic anniversary journey traverses the heart of Americana, featuring the majestic Grand Canyon, the neon glow of Las Vegas, and a century of legendary "Mother Road" nostalgia.

14 nights From £3,599 pp Including Flights
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Katie Guy
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun