Route 66: 14 Day Road Trip Itinerary

Day 1: Chicago

Begin at the Route 66 start sign and lakefront. Explore downtown on foot before collecting your car.

0–1 hours driving · Overnight: Chicago

Day 2: Chicago → Springfield Illinois

Stop briefly at historic roadside signs. In Springfield choose a Lincoln museum or a walk through the historic centre.

3.5–5 hours driving · Overnight: Springfield Illinois

Day 3: Springfield Illinois → St Louis

Arrive early for the riverfront around Gateway Arch. If going inside, book a time compatible with the drive.

2–3 hours driving · Overnight: St Louis

Day 4: St Louis → Springfield Missouri

Break the drive in historic Missouri roadside towns. Keep the evening in Springfield for a diner and rest.

4–5 hours driving · Overnight: Springfield Missouri

Day 5: Springfield Missouri → Tulsa

Optionally include the short historic Kansas section. Walk among Tulsa’s Art Deco buildings downtown.

3–4 hours driving · Overnight: Tulsa

Day 6: Tulsa → Oklahoma City

Make small-town stops along the way. Spend the afternoon walking Bricktown in Oklahoma City.

2–3 hours driving · Overnight: Oklahoma City

Day 7: Oklahoma City → Amarillo

Split this long drive with two rest breaks. Have dinner in Amarillo and prepare fuel and supplies for the desert stages.

4.5–6 hours driving · Overnight: Amarillo

Day 8: Amarillo → Tucumcari

Visit Cadillac Ranch if conditions permit. Explore Tucumcari’s murals and vintage motel signs in daylight.

2–3 hours driving · Overnight: Tucumcari

Day 9: Tucumcari → Albuquerque

Walk the plazas and shops of Albuquerque Old Town. Treat Santa Fe as an extra-night detour rather than squeezing it in.

3–4 hours driving · Overnight: Albuquerque

Day 10: Albuquerque → Holbrook

Check opening and last-entry times for Petrified Forest. Allow several hours beyond the drive if visiting the park.

4–6 hours driving · Overnight: Holbrook

Day 11: Holbrook → Flagstaff

Pause in Winslow before continuing to historic Flagstaff. Add a separate day for the Grand Canyon.

2–3 hours driving · Overnight: Flagstaff

Day 12: Flagstaff → Kingman

Explore historic stops around Seligman. Stay in Kingman so the desert crossing starts fresh the next morning.

2.5–4 hours driving · Overnight: Kingman

Day 13: Kingman → Barstow

Start early for desert conditions and carry water and fuel reserves. Use the main highway where historic sections are closed.

3.5–5 hours driving · Overnight: Barstow

Day 14: Barstow → Santa Monica

Allow a generous buffer for Los Angeles traffic. Finish at Santa Monica Pier and take a final beach walk.

3–5 hours driving · Overnight: End of itinerary

Before you drive

There is no single continuous Route 66 highway. Follow local historic-route signs and add nights if you prefer shorter driving days.

Estimated budget for two

Illustrative October 2026 planning allowances, not live prices or quotes. Two adults, one rental car, a shared mid-range room and 13 nights. Flights, visas, insurance upgrades, deposits and one-way rental fees excluded. Peak season and major activities may exceed these amounts.

• Room per night: 110–190 USD
• Car per day: 60–110 USD
• Food for two per day: 65–110 USD
• Fuel for the trip: 400–650 USD
• Visits, parking and toll allowance: 180–350 USD

Total range including 10% reserve: 4136–7205 USD

Midpoint estimate / per person: 5678 / 2839 USD