In 2026, America’s most legendary highway—Route 66—celebrates its 100th anniversary, and we’re hitting the road to be part of the celebration! From the towering skyline of Chicago to the historic charm of Springfield, we’ll follow the path of the original “Main Street of America,” where neon lights, quirky roadside stops, classic diners and heartfelt stories await around every bend.
Day 1: Monday, April 27
We begin our Route 66 journey in the Windy City—Chicago, the official starting point of the Mother Road. After checking into the Embassy Suites Downtown Magnificent Mile, we settle into our spacious suites, enjoy the hotel’s complimentary amenities and get ready for a special evening.
Dinner tonight is at Berghoff’s, one of Chicago’s oldest restaurants and holder of Liquor License No. 1 following the repeal of Prohibition. The rich wood-paneled dining room, traditional German-American fare and deep history make this a memorable start to our trip. (D)
Day 2: Tuesday, April 28
After a hearty breakfast, we meet our local guide for a Chicago City Driving Tour. From the soaring skyline to iconic neighborhoods, we get a great overview of the city’s architectural splendor and cultural charm. Next, we step inside the legendary Wrigley Field for a behind-the-scenes tour of one of baseball’s most beloved ballparks. Then, we head to Giordano’s for a classic deep-dish pizza lunch—an authentic taste of Chicago! In the afternoon, we board a Chicago River Architecture Cruise, where towering skyscrapers and expert narration bring the city’s design history to life from a relaxing waterside perspective. Tonight, we dive into the 1920s with the Gangster Dinner & Show. After giving the secret password at the speakeasy-style entrance, we enjoy a four-course meal and homemade “hooch,” followed by an entertaining stage show filled with jazz-era tunes, comedy and glamour. It’s an evening of vintage fun and nostalgia! (B, L, D)
Day 3: Wednesday, April 29
This morning, we visit the official Route 66 Begin Sign and take our first steps on the historic road. Our first stop is the Joliet Route 66 Welcome Center, offering exhibits and photo ops to mark the start of our centennial celebration. Along the way to Wilmington, we pass Elwood Park, Abraham Lincoln National Cemetery and the Midewin National Tallgrass Prairie—a unique ecological reserve preserving the natural heritage of Illinois. In Wilmington, we meet the Gemini Giant, a towering roadside muffler man who’s become an icon of Route 66. Lunch is included at Wilmington House Family Restaurant, known for its homestyle cooking. As we continue to Pontiac, we’ll spot the colorful Polka Dot Drive-In in Braidwood and enjoy a rest stop at Wally’s, a retro-modern travel center featuring clean restrooms, delicious snacks, Route 66 memorabilia and a welcoming vibe—“Home of the Great American Road Trip!” In Pontiac, we explore the Route 66 Association Hall of Fame and Museum, filled with artifacts and nostalgic displays. Then we have a trolley tour through the town’s vibrant mural collection—24 stunning life-sized paintings telling the story of small-town America. Dinner is included at the Dwight Family Restaurant, freshly remodeled with classic Route 66 décor. We’ll overnight at the Hampton Inn Pontiac. (B, L, D)
Day 4: Thursday, April 30
Today we head south to Bloomington/Normal to visit Rebury Place, formerly Sprague’s Super Service Station, a beautifully restored vintage gas station and gift shop that transports us back to Route 66’s heyday. In Atlanta, IL, we stop for lunch at the charming Country-Aire Restaurant, then explore the American Giants Museum, a lighthearted and fascinating slice of Americana. Arriving in Springfield, we’re greeted by the warm smile of Bill Shea at the historic Shea’s Gas Station, a treasure trove of Route 66 signs, pumps and stories. Next, we visit Motorhead’s Bar and Grill, a fun and funky restaurant housed in a former Stuckey’s. Dinner tonight is at the Ace Sign Company, a 4th-generation business and museum that’s home to over 85 original signs from Springfield and Route 66. We’ll build our own version of the famous Springfield Horseshoe sandwich, a delicious local specialty, and enjoy homemade root beer and wonderful food in a nostalgic setting. The evening wraps up with the Route 66 Experience, featuring glowing neon signs, vintage billboards, and even a peek at a classic drive-in theater. Our home for the night is the Crowne Plaza Springfield, offering a restful night after a full day of exploration. (B, L, D)
Day 5: Friday, May 1
Our final day begins with a full hot breakfast buffet at the hotel before we head to the inspiring Abraham Lincoln Presidential Museum. Through immersive exhibits, rare artifacts and engaging storytelling, we explore the life and legacy of our 16th president—born just a few miles from the very roads we’ve been traveling. Then, we begin our journey home, with memories of traveling the legendary highway—Route 66. (B)
INCLUDES:
4 nights accommodations: 2 nights at Embassy Suites Chicago; 1 night at Hampton Inn, Pontiac; 1 night Crown Plaza, Springfield; luggage handling
11 Meals: 4 Breakfasts, 3 Lunches, 4 Dinners
A Route 66 expert, personality, guide and navigator from Chicago to Springfield, IL
Chicago Local Guide
Wrigley Field Tour
Chicago River Architecture Tour
Pontiac Route 66 Museum
Ryburn Place
American Giants Museum
Ace Sign Company
Shea’s Gas Station
Route 66 Experience
Abraham Lincoln Presidential Museum
Deluxe motorcoach transportation/driver’s gratuity
Fully Escorted by Jane’s Journeys
PRICE PER PERSON:
Double: $2,637
Triple: $2,399
Quad: $2,292
Single: $3,199
$500 deposit with reservation.
Final payment due February 6, 2026.
Trip Protection is recommended and available for purchase: $120 per person double; $109 per person triple; $104 per person quad; $146 per person single. Trip Protection payment due with deposit. Trip Protection price subject to change.