14 day itinerary
Route66
Itinerary
Route 66, often called the "Main Street of America," is a fantastic journey filled with quirky roadside attractions, stunning landscapes, and rich history. Buckle up, because here’s a fun and engaging 14-day itinerary that will take you from Chicago to Santa Monica, with plenty of stops along the way!
Day 1: Chicago, Illinois
Morning: Start your adventure in the Windy City! Grab a deep-dish pizza at or .
Afternoon: Visit the at Adams and Michigan. Explore and take a selfie with "The Bean."
Evening: Stroll along the and enjoy dinner at a riverside restaurant.
Day 2: Chicago to Joliet (40 miles)
Morning: Head to Joliet and stop at the .
Afternoon: Visit the historic and grab lunch at a local diner.
Evening: Check out the , which has a fascinating history. Spend the night in Joliet.
Day 3: Joliet to Bloomington (70 miles)
Morning: Drive to Bloomington and stop at the .
Afternoon: Explore the . Don’t forget to grab a burger at a classic diner!
Evening: Enjoy a relaxing evening at a local brewery.
Day 4: Bloomington to Springfield (45 miles)
Morning: Head to Springfield, the capital of Illinois. Visit the Abraham Lincoln Presidential Library and Museum.
Afternoon: Check out Lincoln’s Home and the Old State Capitol.
Evening: Dine at a local favorite, like the , famous for its corn dogs!
Day 5: Springfield to St. Louis, Missouri (100 miles)
Morning: Drive to St. Louis. Stop at the iconic and take a tram ride to the top for stunning views.
Afternoon: Visit the , a quirky playground for adults and kids alike!
Evening: Enjoy some St. Louis-style BBQ for dinner.
Day 6: St. Louis to Rolla (100 miles)
Morning: Depart St. Louis and head to Rolla. Stop at the along the way.
Afternoon: Explore the local shops in Rolla and grab lunch.
Evening: Relax at a local motel or campground.
Day 7: Rolla to Lebanon (50 miles)
Morning: Drive to Lebanon and visit the .
Afternoon: Check out the , a classic Route 66 stop.
Evening: Enjoy a cozy dinner at a local diner and spend the night in Lebanon.
Day 8: Lebanon to Springfield, Missouri (40 miles)
Morning: Head to Springfield, MO. Visit the .
Afternoon: Explore the , a drive-through cave!
Evening: Have dinner at a local steakhouse and enjoy some live music if you can find it!
Day 9: Springfield to Tulsa, Oklahoma (180 miles)
Morning: Depart for Tulsa. Stop at the on the way.
Afternoon: Visit the and the .
Evening: Enjoy dinner at a local restaurant and explore the vibrant nightlife.
Day 10: Tulsa to Oklahoma City (100 miles)
Morning: Drive to Oklahoma City. Visit the .
Afternoon: Explore , a revitalized warehouse district with shops and restaurants.
Evening: Have dinner at a local steakhouse and catch a live show if you can!
Day 11: Oklahoma City to Amarillo, Texas (120 miles)
Morning: Head to Amarillo. Stop at the iconic to see the colorful spray-painted cars.
Afternoon: Visit the .
Evening: Enjoy a hearty meal at , famous for its 72 oz steak challenge!
Day 12: Amarillo to Santa Fe, New Mexico (280 miles)
Morning: Depart for Santa Fe. Enjoy the scenic drive through the Texas Panhandle and into New Mexico.
Afternoon: Explore the historic Plaza and visit the .
Evening: Savor some New Mexican cuisine for dinner, like green chile enchiladas.
Day 13: Santa Fe to Flagstaff, Arizona (400 miles)
Morning: Head out early for Flagstaff. Stop at the along the way.
Afternoon: Visit the or take a stroll through downtown Flagstaff.
Evening: Enjoy dinner at a local brewery and soak in the mountain town vibe.
Day 14: Flagstaff to Santa Monica, California (400 miles)
Morning: Depart for Santa Monica. Stop at the iconic .
Afternoon: Spend some time at the , enjoying the beach and the boardwalk.
Evening: Celebrate the end of your Route 66 journey with a sunset dinner overlooking the Pacific Ocean!
And there you have it! A delightful 14-day adventure along Route 66, filled with history, culture, and plenty of fun. Make sure to take lots of pictures and enjoy every moment of this iconic road trip! Safe travels! 🚗✨