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Guided RV Caravan

Route 66 - LA to Chicago

Travel the full length of Route 66 from Santa Monica to Chicago, discovering America's most famous highway. Explore classic diners, quirky roadside attractions, and the nostalgia that makes Route 66 a must-do road trip.

50

Days

100

Events & Meals

2,227

Driving Miles

Starts in Pasadena / San Dimas, CA-Ends in Chicago / Joliet, IL
Route 66 - LA to Chicago — 500x500
+2

Price Lock Guarantee

Price stays locked after your initial deposit.

Interest-Free Payment Plans

Make monthly payments with no added interest.

Exclusive Travel Savings

Save with club discounts and check payments.

Flexible Tour Changes

Switch tours up to 150 days before departure.

What You'll Experience

Eat at Classic Diners - Lou Mitchell's, Pops 66 & More

See Muscle Cars, Retro Gas Stations & Neon Signs

Visit Quirky Roadside Attractions

National & State Route 66 Museums

Route 66 Interpretive Center

International Route 66 Mother Road Festival

St. Louis Gateway Arch Tram Ride

Route 66 Drive-In Movie Theater

Cadillac Ranch & Big Texan Steakhouse

Abraham Lincoln Home National Site

Calico Mining Ghost Town

Historic Railroad, Auto & Transportation Museums

Petrified Forest National Park

Meramec Caverns Underground Tour

Richardsons Native American Trading Post

Cross the Continental Divide in New Mexico

Sunset Dinner at Santa Monica Beach

Route 66 Completion Certificate

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Total Driving Miles

2,227

Average Daily Driving Miles

139

Dates & Pricing

Choose your preferred departure and reserve your spot today.

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Daily Itinerary

50

Days

2,227

Total Driving Miles

139

Average Daily Driving Miles

Easy

Activity Level

|

  • Orientation & Get Acquainted Social
  • Welcome Dinner at Coco Palms
  • Guided Pasadena Highlights Private Motorcoach Tour
  • Rose Bowl Stadium Tour
  • Olvera Street & Union Station
  • The Original Farmer's Market & Bennett's Ice Cream
  • Petersen Auto Museum
  • Guided Santa Monica Highlights Private Motorcoach Tour
  • Breakfast at the Donut Man
  • Hollywood Sign and Walk of Fame
  • Sony Pictures Studio Tour
  • Photo Op Beginning of Route 66 at Santa Monica Pier
  • Sunset Dinner at Santa Monica Beach
  • Free Day to Explore Pasadena
  • OPTIONAL: Original McDonald's Museum
  • OPTIONAL: Inland Empire Military Museum
  • OPTIONAL: Wigwam Village Motel Teepees

Itineraries are subject to change due to weather, road conditions, attraction availability, or other unforeseen circumstances.

Frequently Asked Questions

Answers to the most common questions about tour logistics, booking, deposits, and what to expect on the road.

Planning & Booking

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