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Itineraries in Illinois

We have curated some exceptional holiday itineraries, using our wealth of experience and personal knowledge.

  • Chicago
  • Springfield (IL)
  • St Louis
  • Springfield (MO)
  • Oklahoma City
  • Amarillo
  • Santa Fe
  • Gallup
  • Flagstaff
  • Las Vegas
  • Santa Monica

Get your Kicks on Route 66 and experience one of the world’s most legendary road trips. From Chicago to Los Angeles, this iconic 2,000-mile journey takes you through the heart […]

14 Nights from £2,630pp
  • Chicago

Chicago isn’t just a city, it’s an experience. Nestled on the shores of Lake Michigan, the Windy City offers a dynamic blend of iconic architecture, world-class museums, and an unmistakable […]

4 Nights from £1,649pp
Fly Drives USA
  • Chicago
  • Springfield (IL)
  • St Louis
  • Springfield (MO)
  • Tulsa
  • Oklahoma City
  • Amarillo
  • Santa Fe
  • Gallup
  • Flagstaff
  • Las Vegas
  • Santa Monica

Route 66 spans across North America, from Chicago in the east to Los Angeles in the west. Covering over 2,000 miles, it takes three weeks to complete the journey in […]

21 Nights from £3,835pp
  • New Orleans
  • Baton Rouge
  • Natchez
  • Clarksdale
  • Memphis
  • Florence
  • Nashville
  • Townsend
  • Asheville
  • Pikeville
  • Louisville
  • Champaign
  • Chicago

Blues, Blue Ridge, and BBQ is a journey where unforgettable roads, music and food meet at every turn. From the grand plantations of the Mississippi to Nashville, the heart of […]

15 Nights from £6,625pp
  • Chicago
  • Springfield (IL)
  • St Louis
  • Joplin
  • Oklahoma City
  • Amarillo
  • Santa Fe
  • Gallup
  • Grand Canyon
  • Laughlin
  • Las Vegas
  • Victorville
  • Los Angeles

EagleRider’s Route 66 motorcycle tour follows the iconic “Mother Road” from Chicago to Los Angeles, spanning 2,400 miles and eight states. Steeped in history, nostalgia, and Americana, it passes classic […]

15 Nights from £6,605pp
  • Chicago
  • Springfield (IL)
  • St. Louis
  • Tulsa
  • Oklahoma City
  • Elk City
  • Amarillo
  • Tucumcari
  • Sante Fe
  • Grand Canyon
  • Kingman
  • Las Vegas
  • Hoover Dam
  • Los Angeles
  • San Francisco

This itinerary starts in Chicago and follows the full route to Los Angeles, before taking in the California Coast along Route 1 – so you get two iconic American routes […]

21 Nights from £2,435pp
  • Chicago
  • Lake Michigan
  • Detroit
  • Toronto
  • Niagara Falls
  • Buffalo
  • Toledo

This cross-border motorhome itinerary allows you to explore the tranquil shores of Lake Michigan, experience the ‘Blues’ of Chicago, the ‘Motown’ of Detroit and the ‘Rock ‘n’ Roll’ of Cleveland, all before heading to awe-inspiring Niagara […]

8 Nights from £1,729pp
  • Chicago
  • Saugatuck
  • Mackinac Island
  • Marquette
  • Bayfield
  • Madison
  • Ephraim
  • Milwaukee

The Great Lakes are a freshwater treasure trove of wild islands, unusual geology and legendary waterfalls. Starting in Chicago, this memorable itinerary journeys through Michigan and Wisconsin, exploring Lake Michigan, […]

14 Nights from £3,092pp