Hitching a Ride on Route 66

Apr 6
Apr 10, 2026
Days
Chicago, IL
Hitching a Ride on Route 66
Sold Out

Overview

Celebrate 100 years of America’s most iconic highway with an unforgettable journey down Historic Route 66, from Illinois to the breathtaking Ozark Mountains of Missouri. This centennial tour is packed with charm, nostalgia, the spirit of the open road and loads of Instagram moments. Kick off your adventure in Chicago, traveling through St. Louis & Joplin. Along the way you'll capture classic photo ops with the towering Paul Bunyan Hot Dog Statue, the World's Largest Covered Wagon, and the World's Largest Ketchup Bottle. Step into the legacy of Abraham Lincoln at his presidential library and museum, and enjoy the glowing artistry of vintage neon at the Ace Sign Company. Then browse automotive history at the Route 66 Car Museum in Springfield. We wrap up the trip in Branson for some shopping at Branson Landing, a Sight & Sound Theater production, and the Ancient Ozarks Natural History Museum. Whether you're a history buff, a roadside attraction enthusiast, or simply looking to mark this once-in-a-century milestone, this Route 66 Centennial Tour is the ultimate way to honor a hundred years of the road that shaped America.

Destinations

What’s Included

  • Airfare
  • Luxury motorcoach transportation
  • 4 nights hotel: Drury Inn Springfield, IL (1), Drury Inn Gateway Arch (1), Drury Inn Joplin, MO (1) & Drury Inn Branson, MO or similar (1)
  • 7 meals: 4 breakfasts and 3 dinners
  • Illinois 66 Hall of Fame
  • Paul Bunyan Hot Dog Statue
  • World's Largest Covered Wagon
  • Illinois State Fairgrounds Route 66 Experience
  • Lincoln Presidential Library & Museum
  • Ace Sign Company
  • World's Largest Catsup Bottle  
  • Route 66 Car Museum
  • "Cruisin' into Joplin" and "The American Ribbon"
  • Shopping at Branson Landing
  • Top of the Rock Cart Tour & Ancient Ozarks Natural History Museum
  • Porterage where available
  • Prime Tours Guide

What’s Not Included

  • Meals not listed on the itinerary
  • Travel insurance
  • Tips & gratuities

Price Per person
Sold Out
Double:
$2,695
Single:
$3,195
Triple/Quad:
$2,595
*Pricing Varies - Upgrades Available
Deposit: $
300
Non-refundable administration fee: $
100
Final payment and the non-refundable date:

Tour Details

Stay

Days
4
Nights

Meals

7
Meals
Breakfast and Dinner

Group Size

Medium Group
25-49 people

Activity Level

Light
Activity Level: 2/5
This tour requires average physical activity. You should be in good health, able to climb stairs and walk reasonable distances, possibly over uneven ground and cobblestoned streets.
Requires average physical activity

Age Restrictions

Years of Age

Travel Type

Motorcoach & Airplane
Travel by motorcoach and airplane

Group Air Options

Details Coming Soon

$ /per passenger

$ deposit reserves your spot.

Deposit is refundable until .

*Flight numbers and times subject to change by the airline.

Get a Travel Protection Quote

Now’s the time to consider purchasing a travel protection plan to help protect your travel investment. For your convenience, we offer travel protection through Travelex Insurance Services. For a quote or to enroll, visit the link below or contact Travelex Insurance Services at 800-228-9792 and reference location number 35-6094. 

Travelex Insurance Services, Inc. CA Agency License #0D10209. Insurance coverages underwritten by Zurich American Insurance Company (NAIC #16535, state of domicile: New York), 1299 Zurich Way, Schaumburg, IL 60196. Certain coverages not available in all states. 

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