Route 66 From the Windy City to OKC
Book Now7 Days / 6 Nights
Tour Overview
From the towering skyline of Chicago to the quirky roadside treasures scattered along historic Route 66, this unforgettable journey follows the Mother Road from Chicago to Oklahoma City. Travel a legendary portion of America’s most iconic highway while discovering classic diners, hidden gems, nostalgic roadside attractions, and breathtaking sights along the way. Every mile delivers a story worth telling, filled with classic Americana, unforgettable memories, and the spirit of Route 66.
- Wichita
- Oklahoma City
- 10 Meals Included
- Willis Tower Skydeck
- Gemini Giant
- American Giants Museum
- world’s largest catsup bottle
- Chain of Rocks Bridge
- Ted Drewes Frozen Custard Stand
- Red Rocker
- Baxter Springs Heritage Center & Museum
- Arcadia Round Barn
Tour days tend to be longer and operate at a quicker pace. Expect to stand and walk for long periods of time, with short regular breaks and climb multiple flights of stairs. Some destinations may have changes in altitude and/ or temperature.
Price
- 2499
- Single
- 1989
- Double
- 1869
- Triple
- 1749
- Quad
Terms & Conditions
Cancellation Policy B
$100 Non-Refundable Deposit Per Person | Rates Per Person
Final Payment Due 60 days before departure
To review Village Travel's Cancellation Policies, Click Here
Travel Insurance
Optional Travel Protection Plan Available, for more information Click Here
Itinerary
Day 1 // St. Louis, MO
Buckle up and get ready — the adventure of a lifetime is about to begin! Today we make our way to St. Louis, the eastern gateway to one of America’s most iconic and storied highways. Settle in, get to know your fellow travelers, and start dreaming about the miles of history, quirky landmarks, and unforgettable experiences that lie ahead on the Mother Road!
Day 2 // Chicago, IL
We make our way to the Windy City, where Route 66 was born! Begin at the top — literally — with a visit to the Willis Tower Skydeck, where breathtaking views of Chicago and beyond will leave you speechless. Tonight, we gather for a delicious included dinner before resting up for the road ahead.
Day 3 // Springfield, IL
The journey begins in earnest today as we kick things off with a photo stop at the iconic Route 66 begin sign — the official starting point of the most legendary road in America. Next, snap a photo with the towering Gemini Giant, one of the most beloved roadside attractions along the entire route. Dive deep into the history of this remarkable highway at the Route 66 Association Hall of Fame & Museum, then continue the fun at the American Giants Museum, where the fascinating story of the larger-than-life figures that dot the landscape comes to life!
Day 4 // St. Louis, MO
There’s still plenty of Route 66 magic to uncover as we explore more of Springfield at the Illinois Route 66 Experience before heading south. Stop for lunch at a legendary Mother Road eatery, then snap a picture with the world’s largest catsup bottle — a roadside treasure that never gets old! We’ll walk the historic Chain of Rocks Bridge before wrapping up the evening with a sweet treat at the beloved Ted Drewes Frozen Custard Stand. Save room — it’s worth every bite!
Day 5 // Joplin, MO
Today takes us underground and off the beaten path! Venture into the breathtaking chambers of Meramec Caverns, one of the most spectacular cave systems in the Midwest and a legendary Route 66 attraction in its own right. Back on the surface, snap a photo with the famous Red Rocker before making a stop at the charming Old Riverton Store — a piece of living Route 66 history that has been welcoming road-trippers for generations.
Day 6 // Tulsa, OK
Begin with a visit to the Baxter Springs Heritage Center & Museum, then marvel at the whimsical folk art wonder of Ed Galloway’s Totem Pole Park. Pay tribute to one of Oklahoma’s most beloved sons at the Will Rogers Memorial Museum before snapping a photo with the quirky and iconic Catoosa Blue Whale — a Route 66 classic that never fails to bring a smile. Cap off the adventure with a stop at the vibrant Mother Road Market, where local flavors and one-of-a-kind finds make the perfect souvenir of an unforgettable journey down America’s Main Street!
Day 7 // Home
The final chapter of our Mother Road adventure is a great one! Begin the morning with a stop at the historic Route 66 Village before marveling at the one-of-a-kind Arcadia Round Barn, one of the most photographed landmarks along the entire route. Next, pull up a stool at the legendary Pops 66 and choose your favorite from hundreds of soda pop flavors — a bubbly and delicious Route 66 tradition! We’ll wrap up with a visit to the incredible Cowboy Museum before pointing the coach toward home, hearts full and spirits high after one of the greatest road trips America has to offer. Until next time, Route 66!
Itinerary Map
