June 14th - June 21st, 2026
Route 66
The Chicago to St. Louis stretch of Route 66 offers a captivating journey through the heart of America’s “Mother Road.” Starting in the bustling city of Chicago, this historic route winds through charming small towns, vintage roadside attractions, and scenic landscapes, providing a nostalgic glimpse into mid-20th-century Americana. Perfect for history buffs, road trip enthusiasts, and anyone seeking a slice of classic Americana, this route blends history, culture, and scenic beauty into an unforgettable experience.
Book Now Or Call 330-556-4535Tour Inclusions:
Deluxe Motorcoach Transportation from New Philadelphia
Gratuities for driver, guides
15 Meals
Activity Level
Physical activity rating based on 1 of 5 levels.
Activity Level 2 (Out of 5)
Easy
For those comfortable with light physical activity and minimal walking.
- Walking distance: Up to 1.5 miles per day, spaced throughout the day.
- Pace: Easygoing with scheduled rest opportunities.
- Terrain: Mostly flat with occasional slight inclines, may need to walk up one flight of steps with handrails.
- Elevation: Includes getting on/off buses and occasional stairs (elevators typically available).
- Suitable for: Most people including those using mobility aides.
- Typical activities: Walking tours through flat towns, museum visits, garden paths, light sightseeing.
Attractions
Highlights:
- Chicago’s Gangster Dinner Show
- Historic Route 66 Begin Sign
- Gemini Giant
- Pontiac Route 66 Museum
- Ryburn Place
- American Giants Museum
- Shea’s Gas Station
- Motorheads, ACE Sign Company
- Route 66 Experience
- Louis Gateway Arch
- Route 66 for Beginners with Joe Sonderman
- Chain of Rocks Bridge
- Route 66 State Park
- Abraham Lincoln Presidential Library
- Chicago Architectural Tour
Lodging:
- Union Station Hotel, St. Louis (2 nights)
- Homewood Suites, Chicago (2 nights)
- Hampton Inn, Pontiac
- Crown Plaza, Springfield
- Drury Inn, Indianapolis
Pricing:
$3,495 Per Person Double
$4,495 Per Person Single
Tour Videos
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Your Itinerary
Day One
Depart from New Philadelphia for Chicago and check in to your hotel. Step back to 1929 for a night of speakeasy glamour! Give the password to join Vito and the gang for a four-course dinner, homemade hooch, and a lively 90-minute stage show packed with 1920s tunes and hilarious comedy. An unforgettable evening of gangsters, flappers, fantastic food, and nonstop fun awaits! (Dinner Show
Day Two
Spend the day discovering Chicago’s iconic highlights. Begin with a visit to legendary Wrigley Field, home of the Cubs, before savoring an iconic food tour featuring deep-dish pizza, hot dogs, and other Windy City favorites. Cruise the Chicago River on a world-famous architecture tour, then end the evening with a classic German-American dinner at the historic Berghoff Restaurant. (Breakfast, Lunch, Dinner)
Day Three
Kick off your Route 66 adventure at the iconic “Begin Historic Route 66” sign in downtown Chicago, the perfect place for photos and to officially start the journey. Travel south to Wally’s, a modern yet retro-inspired stop where travelers can fuel up, shop Route 66 memorabilia, and enjoy classic roadside treats. Continue to Wilmington to meet the Gemini Giant, a towering fiberglass “Muffler Man” dressed as a spaceman, one of the most famous roadside attractions on the route. Next, head to Pontiac and step inside Route 66 Museum, where vintage cars, memorabilia, and interactive exhibits bring the golden age of road travel to life. Then relax on a guided trolley tour through the town to view 24 stunning, life-like murals that show local history and Route 66 culture. The day concludes in Dwight with a hearty dinner at the welcoming Dwight Family Restaurant, a local favorite known for generous portions, friendly service, and the kind of comfort food that has fueled Route 66 travelers for decades. (Breakfast, Dinner)
Day Four
Spend a full day exploring the heart of Route 66. Begin at Ryburn Place, a historic stop known for its nostalgic roadside attractions and classic Americana charm, perfect for photos and soaking in Mother Road history. Next, visit the American Giants Museum, where towering fiberglass statues and exhibits celebrate the larger-than-life characters and culture of Route 66. Stop at Shea’s Gas Station, a beautifully restored vintage station offering a glimpse into the golden age of road travel. End the day with dinner at the Ace Sign Company, then experience the Route 66 Experience at night—a self-guided tour through 92 Illinois communities, featuring neon signs, vintage billboards, a drive-in theater, Legends Neon Sign Park, and tributes to the iconic Muffler Men. (Breakfast, Dinner)
Day Five
Spend the day exploring history and culture. Begin at the Abraham Lincoln Presidential Museum in Springfield, where immersive exhibits bring Lincoln’s life and legacy to life. Travel to St. Louis and check into the Union Station Hotel for a two-night stay. This historic, beautifully restored train station features grand architecture, soaring ceilings, elegant guest rooms, modern amenities, and easy access to dining, shops, and attractions. Visit the soaring Gateway Arch for breathtaking city and river views, explore the Missouri History Museum, and conclude your days with intimate private dinners at the Key Bistro, savoring locally inspired cuisine in a welcoming setting. (Breakfast, Dinner)
Day Six
This morning starts with “Route 66 for Beginners” with Joe Sonderman which offers a comprehensive introduction to America’s iconic highway, blending historical insights with practical travel tips. Sonderman, a seasoned Route 66 expert and author of over 15 books on the subject, provides readers with a roadmap to explore the Mother Road’s rich heritage and attractions. Next take a walk across the Chain of Rocks Bridge, spanning the Mississippi River with stunning views and a unique 22-degree bend in the middle. Head to Crown Candy Kitchen, a beloved local spot known for hearty sandwiches, hand-dipped malts, and old-fashioned charm. Make a stop at Route 66 State Park, where scenic trails and historic markers celebrate the Mother Road. End the day with a sweet treat at Ted Drewes Frozen Custard, enjoying rich, creamy custard in one of St. Louis’ most iconic dessert spots. (Breakfast, Lunch)
Day Seven
After breakfast at the Station Grill, enjoy a leisurely morning before departing for Indianapolis where our journey continues with a touch of charm along the downtown canal. Experience the serenade of old-world gondoliers as you glide through the waterways, complete with a light snack at the Fresco Italian Café. Last, check in to the Drury where you can relax and enjoy their “Kick-Back” of drinks and heavy snacks. (Breakfast, Kickback at Drury)
Day Eight
Today we make our way home with great memories of great American Landmarks. (Breakfast)
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