The 14‑day Route 66 itinerary is designed for travelers who want to slow down and savor the journey. With extra nights in Springfield, Tucumcari, Albuquerque, and Flagstaff, this plan allows more time to explore quirky roadside attractions, historic landmarks, and authentic motels along the way. Each day includes mileage, suggested times, and overnight stays at legendary Route 66 lodgings.
14‑Day Route 66 Essentials Itinerary with Times and Overnight Stays
Day 1: Chicago → Springfield, IL (~200 miles, 3–4 hrs)
- 08:00 AM – Breakfast at Lou Mitchell’s (classic Route 66 start)
- 09:00 AM – Depart Chicago, stop in Joliet for Route 66 Welcome Center
- 11:00 AM – Pontiac Route 66 Museum & murals (photo ops)
- 02:00 PM – Arrive Springfield, Cozy Dog Drive‑In
- Overnight: Route 66 Hotel & Conference Center
Day 2: Springfield (local day)
- 10:00 AM – Abraham Lincoln Presidential Library
- 12:00 PM – Lunch downtown Springfield
- 02:00 PM – Route 66 Drive‑In Theater (retro experience)
- Overnight: Route 66 Hotel & Conference Center
Day 3: Springfield → St. Louis (~100 miles, 2 hrs)
- 09:00 AM – Depart Springfield
- 11:00 AM – Chain of Rocks Bridge (photo stop)
- 01:00 PM – Lunch downtown St. Louis
- 02:00 PM – Gateway Arch (iconic landmark)
- Overnight: Holiday Inn Route 66 • La Quinta Inn • Wayside Motel
Day 4: St. Louis → Rolla (~110 miles, 2 hrs)
- 09:00 AM – Depart St. Louis
- 10:00 AM – Meramec Caverns (cave tour)
- 12:00 PM – Lunch in Cuba, MO (murals + Wagon Wheel Motel café)
- 02:00 PM – Arrive Rolla, explore Route 66 sites
- Overnight: Wagon Wheel Motel, Cuba
Day 5: Rolla → Tulsa (~280 miles, 5 hrs)
- 08:00 AM – Depart Rolla
- 11:00 AM – Springfield Route 66 Car Museum
- 02:00 PM – Blue Whale of Catoosa (roadside stop)
- 04:00 PM – Arrive Tulsa
- Overnight: Campbell Hotel
Day 6: Tulsa → Oklahoma City (~120 miles, 2–3 hrs)
- 09:00 AM – Depart Tulsa, Route 66 Historical Village
- 11:00 AM – Lunch at Rock Café, Stroud
- 01:00 PM – Round Barn, Arcadia
- 02:00 PM – Pops Soda Ranch (unique sodas)
- 03:00 PM – Arrive Oklahoma City, Cowboy Museum
- Overnight: Skirvin Hilton
Day 7: Oklahoma City → Amarillo (~260 miles, 4–5 hrs)
- 08:00 AM – Depart OKC, stop at Lucille’s Gas Station (~09:30 AM)
- 11:00 AM – Clinton Route 66 Museum
- 01:00 PM – Lunch en route
- 04:00 PM – Cadillac Ranch (bring spray paint!)
- 05:00 PM – Arrive Amarillo
- Overnight: Big Texan Motel
Day 8: Amarillo → Tucumcari (~120 miles, 2 hrs)
- 09:00 AM – Depart Amarillo
- 10:00 AM – Midpoint Café (Adrian, TX)
- 12:00 PM – Arrive Tucumcari (murals, Tee Pee Curios)
- Overnight: Blue Swallow Motel • Motel Safari
Day 9: Tucumcari (local day)
- 10:00 AM – Explore murals & neon signs
- 12:00 PM – Lunch at Del’s Restaurant
- 02:00 PM – Visit Tucumcari Historical Museum
- Overnight: Blue Swallow Motel • Motel Safari
Day 10: Tucumcari → Albuquerque (~180 miles, 3 hrs)
- 09:00 AM – Depart Tucumcari
- 11:00 AM – Santa Rosa Auto Museum
- 02:00 PM – Arrive Albuquerque (Route 66 Diner, neon signs)
- Overnight: Hotel Albuquerque at Old Town • El Vado Motel
Day 11: Albuquerque (local day)
- 10:00 AM – Explore Old Town Albuquerque
- 12:00 PM – Lunch at Frontier Restaurant
- 02:00 PM – El Vado Motel courtyard (retro revival)
- Overnight: Hotel Albuquerque at Old Town • El Vado Motel
Day 12: Albuquerque → Flagstaff (~320 miles, 5–6 hrs)
- 08:00 AM – Breakfast at Route 66 Diner
- 10:00 AM – Gallup murals stop
- 12:00 PM – Petrified Forest National Park
- 02:00 PM – Wigwam Motel, Holbrook (sleep in a teepee!)
- 05:00 PM – Arrive Flagstaff
- Overnight: Wigwam Motel, Holbrook • Little America Hotel
Day 13: Flagstaff (local day)
- 10:00 AM – Lowell Observatory
- 12:00 PM – Lunch downtown Flagstaff
- 02:00 PM – Explore Historic Downtown shops
- Overnight: Wigwam Motel, Holbrook • Little America Hotel
Day 14: Flagstaff → Santa Monica (~460 miles, 7–8 hrs)
- 07:00 AM – Depart Flagstaff, stop at Meteor Crater (~08:00 AM)
- 10:00 AM – Seligman (burger + revival town)
- 12:00 PM – Hackberry General Store
- 02:00 PM – Oatman burros (wild burros experience)
- 06:00 PM – Arrive Santa Monica Pier (Route 66 End Sign)
- Overnight: Fairmont Miramar Hotel • Sea Shore Motel
Tips
- Book Blue Swallow, Wigwam, Motel Safari, and El Vado early — they sell out quickly.
- Mix retro motels with modern hotels for comfort.
- Treat overnight stays as part of the Route 66 experience, not just stopovers.
Ready to hit the Mother Road?
Pick your itinerary, fuel up, and start your Route 66 adventure today.