Rt. 66 Chicago To St. Louis

Rt. 66 originates in Chicago, Illinois where this Mother Road Experience begins

Experience Rt. 66 for your first time or relive childhood memories of the open road, the Illinois Mother Road Experience has something for everyone!

Rt. 66 is 2,448 miles of open road across America, and often times travelers are wanting to get down the road breeze right through Illinois, and in doing so they miss out on some amazing Rt. 66 history and Americana often overlooked. The Illinois countryside is rich in old Rt. 66 roadside attractions and hidden stops. We are going to see, and experience major Rt. 66 sites and we will spend some time seeking this hidden history of Rt. 66 from Chicago to St. Louis on the 297 miles of Illinois open road.

Rt. 66 memories and Americana of the 1950s and 60s

Travel planning isn’t always an easy task for groups. There’s a lot to consider such transportation, hotels, site entries, meals, and more, and it all has to fall in line for the trip to work for everyone’s enjoyment. If you’re not up for that task, we would like to take that on that task for your group and save you time and frustration trying to do the planning on your own. A Traveler’s Rest representative will assist you through the whole process from planning to returning safely home with your group.

School class trips – Band trips – Scouting groups – Theater groups – Church groups – Bank groups – Reunion groups – Military groups – Park district groups – Scholar groups – Senior groups


Classic Cars


Cruising Music

Ambler’s Texaco

Old Gas Stations


Vintage Signs


Soda Fountains


Hot Dogs


Apple Pie


Novelty Attractions

Why choose the Route 66 Experience?

  • You’ll be supporting a small but experienced family company that is independently  owned.
  • Competitive pricing because we’re a smaller company and don’t have all of the corporate expenses to feed. 
  • Knowledgeable and professional guides with years of experience. 
  • We offer educational and historical programs for students and groups for an interactive experience the other companies don’t offer.

Ready to start planning your Route 66 Experience trip?

A Traveler’s Rest rep will assist you through the entire process

Step 1: Contact us with specific details about your group.
Step 2: Select the sites you want to visit.
Step 3: Select your meal/hotel options.
Step 4: Review your itinerary with your rep.
Step 5: Price out your trip/Sign contract
Step 6: Sell your trip to your group members.
Step 7: Pay for all trip members
Step 8: Final review of travel plans
Step 9: Show up on time for departure                          
Step 10: Enjoy your Route 66 Experience!

Cost of Tours

There’s a number of factors that influence the cost of experience tours; gas prices, entry fees, program costs, food prices, etc. We want your business, so we work to give you the experience tour that you would expect, but also to keep our prices low and competitive.

Included in the price:

Not included:

Our Rt. 66 guide is a professionally trained and certified tour guide who has a wealth of Rt. 66 information and a knowledgeable route historian.


After a long day of excitement and site seeing a good meal and rest is important. The Drury Inn hotels provide clean and comfortable rooms at an affordable price.

The food you enjoy is an important part of travel and we understand that. The Drury Inn hotels offer a daily “Kick-Back Time” from 5-7:30 pm where you can enjoy complimentary food and beverages while you socialize and make new friends on your tour.

Your lunches are self-pay so you can make the choices you want. There will be plenty of opportunities for tasty treats and snacks throughout the day to keep you going. Included with your travel packet you will find menus of all of your meal options.

Sample Itineraries

There are a number of factors that can influence travel plans so each of our itineraries are customized to fit the needs of your group. Some sites can be quick visits, but a number of sites are multi-hour visits.

We are unable to guarantee that you will get site reservations in the order you select due to reservations already in the system taking up time slots. We will do our best for you, but best advice here is to be flexible and get your requests to us as soon as possible. Single or multiple day itineraries possible.

Route 66 has a wide range of activities for a wide range of interests that displaying sample itineraries wouldn’t do justice to the numerous possibilities. It really depends on the make-up up your group and the time you have to visit. Contact your TRT rep to brainstorm the possibilities for your group and to receive sample itineraries.

Travel Day

Fly or train into Chicago, Illinois
Transfer to your hotel for check-in where you will be met by your Rt. 66 host and tour guide.

  • Hotel Cambria, 3pm check-in, if early hang out
    Group introduction at dinner
  • Dinner – Gino’s Pizza

Day 1

  • Hotel breakfast
  • Driving tour of Jackson Park
  • Hyde Park and Kenwood neighborhoods
  • Driving the Loop and Michigan Avenue
  • Stop at Marquette Building
  • Stop at Millennium Park, the “Bean”
  • Lunch – Walnut Room
  • Macey’s 
  • Architectural River Cruise
  • Return to hotel
  • Dinner TBD

Day 2

  • Hotel breakfast
  • Check-out
  • Leave Chicago for the open road through Illinois on Rt. 66.
  • Drive-by Collins Street Prison
  • Stop at Gemini Giant
  • Dwight, stop at Ambler’s Texaco
  • Odell, stop Standard Oil Gas Station
  • Pontiac – lunch at The Filling Station
  • Rt. 66 Hall of Fame Museum
  • Atlanta, drive-by Downy Building
  • Stop for pie, Palms Grill Café
  • Lincoln, Lincoln Heritage Museum
  • Drive by the Old Mill and world’s largest covered wagon, ole Abe sitting there
  • Springfield, check-in Drury Inn
  • Dinner at hotel

Day 4

  • Hotel breakfast
  • Abraham Lincoln Presidential Museum
  • The Lincoln Tomb
  • Lunch – Cozy Dog Drive-in
  • The Lincoln Home
  • Driving tour, Rt. 66 sites
  • Stop Ace Sign Co. vintage sign museum
  • Dinner, Maldaner’s, oldest restaurant on Rt. 66

Day 5

  • Hotel breakfast
  • Back on the Mother Road to St. Louis
  • Auburn, photo opp original Rt. 66 bricks
  • Stop Girard, Docs Soda Fountain
  • Carlinville, drive-by Cannonball jail
  • Litchfield, Rt.66 museum & welcome center
  • Lunch – Ariston Café  
  • Mt. Olive, drive-by Soulsby service station
  • Madison, stop at Chain of Rocks Bridge
  • Collinsville, stop at Cahokia Mounds
  • Arrive late afternoon in STL
  • Check-in Drury Inn
  • Dinner at the hotel
  • Ted Drewes Frozen Custard

Day 6

  • Hotel breakfast
  • Explore Union Station and Aquarium
  • Cathedral Basilica
  • Lunch – Favazza’s
  • Drive through Forrest Park
  • Visit the Federal Courthouse and Jefferson Expansion Museum and the Arch
  • Mississippi River dinner cruise

Day 7

  • Hotel breakfast
  • Check-out
  • Transfers to transportation hub

Route 66 Group Tour Request

We’ve escorted individuals, families, politicians, generals, admirals, rock stars, all kinds of groups, and nearly 60,000 school kids since 2005!