Chicago, The Great Lakes and Route 66 holidays

Holidays to Chicago, The Great Lakes & Route 66

Begin where the adventure starts – Chicago. Set dramatically against the vast expanse of Lake Michigan, this is a city that never stops surprising. More than 15 miles of sandy beach fringe the lakefront, yet most first-time visitors arrive expecting only skyscrapers and deep-dish pizza. They get both, of course, but also so much more – the Magnificent Mile for world-class shopping, Millennium Park for Cloud Gate and open-air concerts, and the Field Museum for millions of years of natural history. Spend time in Chicago's neighbourhoods and you'll quickly discover where the real magic happens: diverse pockets of Greek, Mexican, Middle Eastern and Asian culture, each with their own restaurants, festivals and street life that rewards a slow wander.

From Chicago, head south and west into Illinois, where Great Rivers Country unfolds along the mighty Mississippi and Illinois Rivers. Picturesque towns, Amish communities in the rolling central plains and the dramatic bluffs of Starved Rock State Park – which genuinely takes your breath away on a clear morning – offer a quieter, deeply American counterpoint to the city's energy. Springfield, the state capital, carries the weight of history proudly. This is Lincoln's Illinois, where monuments, museums and the echoes of a presidency shape every visit. Each September, the Mother Road Festival celebrates the spirit of Route 66 right here in Springfield, making it a natural gateway to the highway ahead.

Crossing into Missouri, the journey deepens. St. Louis announces itself with the Gateway Arch – that extraordinary 630-foot curve of steel marking the point where America turned its eyes west. Ride the tram to the top and the view across the Mississippi is something you won't forget. The city's blues heritage runs just as deep: the National Blues Museum, the Delmar Loop and legendary live venues like Broadway Oyster Bar keep that tradition gloriously alive. Kansas City, meanwhile, pulses with a jazz legacy born in the storied 18th & Vine district, where the American Jazz Museum does full justice to the ghosts of Charlie Parker and Count Basie. Kansas City barbecue – smoky, sweet, spectacular – is reason enough to linger an extra night.

Then there's Route 66 itself, threading through the heart of the region like a greatest hits of American road-trip culture. Missouri's stretch alone delivers retro drive-ins, glowing neon, frozen custard stands and classic diners where the pie is always worth ordering. Cross into Illinois and the road carries you through Springfield and on to the legendary stretch where fibreglass giants and vintage motor courts appear around every bend. The Gemini Giant stands sentinel in Wilmington; pull over, because you'll want the photograph. Further west, the Cadillac Ranch awaits in Texas. Every stop tells a story, and after travelling this route ourselves, we can say the cumulative effect is something quite special.

Taken together, Chicago, the Great Lakes and Route 66 offer one of North America's most rewarding and richly layered journeys – a trip equally at home as an escorted tour or a freewheeling self-drive adventure.

Seven reasons to visit Chicago, the Great Lakes and Route 66

• Chicago's skyline, beaches and blues bars – a world-class city that consistently exceeds every expectation.
• Route 66 road-trip magic – neon signs, retro diners and quirky roadside Americana across three iconic states.
• Gateway Arch and Missouri's legends – jazz, blues, BBQ and the story of America's westward expansion.
• The Great Lakes shoreline – 15 miles of Chicago beach and the vast, shimmering beauty of Lake Michigan.
• History at every turn – Lincoln's Springfield, Mark Twain's Hannibal and the Pony Express trail of St. Joseph.
• Food to remember – deep-dish pizza, Kansas City BBQ, New Mexican green chile and legendary roadside pie.
• Flexible and rewarding to explore – equally brilliant as an escorted tour, self-drive adventure or multi-centre holiday.