Chicago Holidays
Sample itineraries
Route 66 - The Classic Tour
Route 66, The Mother Road from Chicago to Los Angeles, who can resist this iconic 2448 mile journey through 8 states and 3 time zones.
Multi centre holiday - Chicago, Memphis and New Orleans.
Music lover or not, you'll adore this three-centre holiday. From the towering sky-scrapers of Chicago,down to the Home of the Blues AND the Birth Place of Rock'N'Roll, Memphis ... ending in The Big Easy, sexy New Orleans...
View Multi centre holiday - Chicago, Memphis and New Orleans.
Route 66 - The Mother Road
Route 66, The Mother Road from Chicago to Los Angeles! Who can resist this iconic 2,448 mile journey through 8 states and 3 time zones? Take the holiday of a lifetime and drive the classic Route 66 with Bon Voyage.
Route 66 Guided Motorcycle Tour™
EagleRider's world famous guided Route 66 motorcycle tour travels the original Route 66 over 2,400 miles from Chicago to Los Angeles.
Northern Explorer - 10 night Rail Adventure
The Northern Explorer gives you the opportunity to see the rugged Northwest States, but not before sampling the delights of Chicago. Then you're off into the wilderness aboard the Empire Builder through picturesque valleys and beautiful mountains to Seattle and then down the awe inspiring pacific coast to San Francisco. This adventure tour takes you back to nature without leaving the comfort of your train.
Jazz and Blues - 8 night Rail Adventure
Journey south through the very heart of the USA music scene as you head from Chicago to New Orleans, whether exploring the...
The Californian Zephyr
Following the wagon tracks of the great pioneers, the Zephyr is the flagship of Amtrak's fleet, a super liner with an all-window panoramic lounge car and a tick list of iconic Americana that includes the cornrows of Nebraska, the Rockies, the Sierra Nevada, Omaha, Denver, Salt Lake City and San Francisco, 56 hours and 2,438 miles - a classic journey!
Jesse James Loop - 8 night Rail Explorer
This rail adventure sets you off on the trail of the infamous Jesse James, Americas most famous outlaw. Start your trip in Chicago before heading to Gateway to the West; St Louis with its iconic arch, travelling west ot Kansas City you will have time to visit St Joseph the home of Jesse James and also the birth place of the Pony Express a trip here from Kansas City is a must.
The Great Expectations Tour - The Great Lakes of North America
The wonderful Great Lakes Region of America truly have something for everyone, from the skyscrapers of Chicago to iconic Route 66, from quaint Mackinac Island to mighty Lake Superior.
View The Great Expectations Tour - The Great Lakes of North America
A Great Lakes Adventure-Deluxe Tour
Led by massive Lake Superior, the Great Lakes region is a land of water, woods, hills, lighthouses, ships and wildlife. Amidst all this is a diverse group of very friendly people, descendants of Native Americans, French-Canadians, English, Finns, Swedes, Italians, Greeks and Croatians who settled the area.
Today’s culture is a relaxed and comfortable mosaic of lumberjacks, sailors, miners, farmers and fisherman who work right alongside college professors, artists, craftsmen, technology buffs, and merchants. As you meander along scenic roads, through historic towns and natural pathways, you get the impression that local citizens really like the area and genuinely want you to enjoy yourself too.
