Luxury Chicago & Route 66 holidays
USA
A striking fusion of architectural elegance and nostalgic Americana – Chicago and Route 66 promise a journey rich in culture, cuisine and classic road-trip charm.
USA
A striking fusion of architectural elegance and nostalgic Americana – Chicago and Route 66 promise a journey rich in culture, cuisine and classic road-trip charm.
Chicago is a city that surprises – its skyline a testament to innovation, its streets alive with jazz, deep-dish indulgence and lakeside tranquillity. From the sophistication of the Magnificent Mile to the creative buzz of Millennium Park, this urban playground offers a refined escape with a warm Midwestern welcome.
Beyond the city, Route 66 begins its legendary path through the heart of America. This iconic highway evokes a bygone era of diners, neon signs and open-road freedom – a nostalgic adventure that starts in the Windy City and winds through small towns and sweeping landscapes. Whether it’s a weekend immersed in Chicago’s finest hotels or a leisurely drive into the country’s cultural soul, this region invites travellers to experience the USA with style and substance. Carrier’s tailor-made itineraries ensure every moment is steeped in luxury, authenticity and discovery.
"Chicago is a town, a city that doesn't ever have to measure itself against any other city."
The leading line-up
Chicago & Route 66
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![North America & Canada, Chicago, Fairmont Chicago, Aria Restaurant]()
Fairmont Chicago, Millennium ParkCommanding a central location to all the sights and attractions of the Windy City, just steps from Millennium and Grant Parks, Navy Pier, the Magnificent Mile and Lake Michigan. An authentic spa experience awaits after busy day exploring the city, with treatments including personalised massages and a candlelight couples massage.
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![USA, Luxury Chicago Holidays, Four Seasons Hotel Chicago, Swimming pool]()
Four Seasons Hotel ChicagoOccupying the higher floors of an imposing skyscraper with panoramic vistas over the Chicago skyline and Lake Michigan, this is Four Seasons living at its most exclusive. The Hotel’s location atop The Magnificent Mile is perfect for city exploration with guided architectural tours available.
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![USA, Luxury Chicago Holidays, The Peninsula, Chicago, Spa pool]()
The Peninsula ChicagoLocated close to the designer studios and department stores of Chicago’s Magnificent Mile shopping district, this prestigious favourite accomplishes a home away from home feel. Its generously proportioned rooms and suites all offer unforgettable urban vistas.
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Explore the rest of the US
From snow-dusted summits to palm-lined beaches; from neon metropolis nights to sweeping desert horizons – the USA is a study in contrasts, where every state has its story.
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United States of America
Arizona & Utah
ExploreA landscape of cinematic beauty and spiritual stillness, Arizona and Utah are the gateway to the American Southwest’s most awe-inspiring natural wonders.
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California
ExploreThe Golden State is a journey through sun‑drenched vineyards, glamorous cities, dramatic coastlines and the laid‑back beauty of Pacific shores.
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Florida
ExploreA land of year‑round sunshine where theme park thrills sit alongside serene stretches of coast and charming seaside towns.
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![A beach scene featuring tall palm trees, surrounded by scattered rocks along the shore.]()
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Hawaii
ExploreThe Aloha State greets with a welcoming spirit; a tropical archipelago where volcanic landscapes meet golden sands and island traditions.
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![Time lapse of a road creating blurred lights in Las Vegas city at night]()
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Las Vegas & Nevada
ExploreLas Vegas shimmers in the desert, a dazzling playground of glittering lights, world‑class entertainment and indulgent experiences.
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![Small white lighthouse on a rocky shoreline]()
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New England
ExploreBoston & New England charm with historic colonial towns, fiery autumn foliage, picturesque harbours and tranquil seaside retreats.
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![Aerial view of Manhattan, New York, United States of America]()
United States of America
New York
ExploreBuzzing with iconic landmarks, world‑class cultural institutions and the glamour of Manhattan nights that never truly sleep.
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United States of America
Seattle & The Pacific Northwest
ExploreA region where urban sophistication meets untamed nature, Seattle and the Pacific Northwest offer a refreshing blend of culture, coastline and evergreen wilderness.
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![A busy Mardi Gras in Bourbon street]()
United States of America
Southern States
ExploreThe South beats to a slower rhythm with soulful jazz in New Orleans, genteel streets in Charleston and rich, authentic Southern flavours to savour.
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United States of America
The Rocky Mountain States
ExploreThe USA’s side of the Rockies stretch skyward with majestic alpine towns, powder‑soft slopes and vast national parks filled with wonder.
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United States of America
Washington D.C. & The Capital Region
ExploreA cultural powerhouse where history, politics, and sophistication converge, Washington D.C. and its surrounding region offer a refined and thought-provoking American escape.
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