📸 The Ultimate Route 66 Road Trip: 14 Days from Chicago to Santa Monica

🛣️ Route 66 Road Trip Overview

Get ready to embark on the ultimate American road trip—Route 66! Stretching from the heart of Chicago all the way to the sunny shores of Santa Monica, this legendary highway spans over 2,400 miles and is packed with history, quirky roadside attractions, small-town charm, and stunning scenery. Whether you're a first-time traveler or a seasoned road tripper, this 14-day itinerary will guide you through the best stops, sights, and experiences along the way. Buckle up and let the adventure begin!

  • Starting Point: Chicago, Illinois
  • Ending Point: Santa Monica, California
  • Total Distance: ~2,400 miles (3,862 km)
  • Typical Duration: 2–3 weeks
    • Fast Pace: 7–10 days (less time for stops)
    • Balanced Pace: 14–17 days (time to enjoy key attractions)
    • Leisurely Pace: 3–4 weeks (thorough, relaxing, with detours)

🗓️ Route 66 – 14-Day Itinerary

Day 1: Chicago, IL

  • Activities:
    • Snap a photo at the “Begin Route 66” sign
    • Visit the Art Institute or Millennium Park
    • Eat at Lou Mitchell’s Diner
  • Overnight: Chicago

Day 2: Chicago → Springfield, IL (~200 miles)

  • Stops:
    • Gemini Giant (Wilmington)
    • Route 66 Museum (Pontiac)
    • Cozy Dog Drive-In (Springfield)
  • Overnight: Springfield

Day 3: Springfield → St. Louis, MO (~100 miles)

  • Stops:
    • Lincoln’s Home
    • Route 66 Drive-In Theater (Litchfield)
    • Gateway Arch
  • Overnight: St. Louis

Day 4: St. Louis → Springfield, MO (~215 miles)

  • Stops:
    • Meramec Caverns
    • Route 66 State Park
    • Devil’s Elbow Bridge
  • Overnight: Springfield, MO

Day 5: Springfield, MO → Tulsa, OK (~180 miles)

  • Stops:
    • Cars on the Route (Galena, KS)
    • Rainbow Bridge
    • Blue Whale of Catoosa
  • Overnight: Tulsa

Day 6: Tulsa → Oklahoma City (~110 miles)

  • Stops:
    • Route 66 Interpretive Center (Chandler)
    • Pops Soda Ranch (Arcadia)
    • National Cowboy & Western Heritage Museum
  • Overnight: Oklahoma City

Day 7: Oklahoma City → Amarillo, TX (~260 miles)

  • Stops:
    • Lucille’s Historic Gas Station
    • Oklahoma Route 66 Museum (Clinton)
    • Cadillac Ranch (Amarillo)
  • Overnight: Amarillo

Day 8: Amarillo → Tucumcari, NM (~115 miles)

  • Stops:
    • Midpoint Café (Adrian, TX)
    • Route 66 Monument (Tucumcari)
    • Blue Swallow Motel (overnight stay recommended!)
  • Overnight: Tucumcari

Day 9: Tucumcari → Santa Fe, NM (~165 miles via Santa Rosa)

  • Stops:
    • Route 66 Auto Museum (Santa Rosa)
    • Explore Santa Fe Plaza, art galleries, and adobe architecture
  • Overnight: Santa Fe

Day 10: Santa Fe → Gallup, NM (~200 miles)

  • Stops:
    • Albuquerque Old Town (brief stop)
    • Continental Divide
  • Overnight: Gallup

Day 11: Gallup → Holbrook, AZ (~95 miles)

  • Stops:
    • Petrified Forest National Park
    • Wigwam Motel
  • Overnight: Holbrook

Day 12: Holbrook → Kingman, AZ (~230 miles)

  • Stops:
    • Standin' on the Corner Park (Winslow)
    • Meteor Crater
    • Route 66 Museum (Kingman)
  • Overnight: Kingman

Day 13: Kingman → Santa Monica, CA (~340 miles)

(Consider overnighting in Barstow or San Bernardino to break it up)

  • Stops:
    • Oatman (wild burros and old west vibes)
    • Elmer’s Bottle Tree Ranch
    • Wigwam Motel (San Bernardino)
  • Optional: Stay in Barstow/San Bernardino to arrive fresh in Santa Monica
  • Overnight: Santa Monica

Day 14: Explore Santa Monica, CA

  • Activities:
    • Santa Monica Pier (official end of Route 66)
    • Venice Beach
    • Relax and celebrate the end of your trip!


🧭 Notes:

  • Adjust for personal preferences, weather, and detours.
  • Add buffer days if you want to visit places like the Grand Canyon (from Williams, AZ) or Las Vegas (from Kingman).
  • For a slower pace, consider stretching this to 17–18 days.

 

Congratulations—you’ve completed your journey down Route 66! From big city lights to peaceful desert landscapes, you've experienced the spirit of America one mile at a time. This road trip is more than just a drive; it’s a journey through time, culture, and classic Americana. We hope the memories you’ve made will last a lifetime, and maybe even inspire your next great adventure. Safe travels, and thanks for riding the Mother Road!

                                                                                                                                                                                                        

Tisha Jones, owner of E Jones Travel, specializes in cruises, family trips, getaways, accessible travel, and budget-friendly adventures.  Whether it's your dream vacation or a quick escape, Tisha offers expert guidance and personalized service.

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Route 66 Itinerary

Route 66 Itinerary – Chicago to Santa Monica (14 Days)

Day 1: Chicago, IL

Start your journey at the "Begin Route 66" sign in Chicago. Explore Millennium Park and grab breakfast at Lou Mitchell’s.

Begin Route 66 Sign Millennium Park

Day 5: Springfield, MO → Tulsa, OK

Visit the Blue Whale of Catoosa and the Rainbow Bridge in Kansas. Explore Tulsa’s art deco downtown.

Blue Whale Catoosa Rainbow Bridge Kansas

Day 10: Santa Fe → Gallup, NM

Pass through Albuquerque and reach Gallup, known for its Route 66 neon signs and Native American art.

Old Town Albuquerque Gallup Route 66 Neon

Day 14: Santa Monica, CA

End your journey at the Santa Monica Pier. Celebrate the end of your road trip at the "End of the Trail" sign.

Santa Monica Pier End of Trail Sign

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