If you’re planning a Route 66 road trip, one of the first big questions is:

Do we drive from Chicago to Santa Monica — or the other way around?

And what if we don’t have enough time to drive the full Route 66?

This is one of the most important decisions you’ll make when planning your Route 66 itinerary. The starting point influences your pacing, landscape progression, emotional experience, and even flight logistics.

After driving Route 66 and helping thousands of travelers plan their trip, here’s how to choose the smartest starting and finishing point for your journey.

The Classic Route: Chicago to Santa Monica 🏁

The traditional Route 66 road trip starts in Chicago and ends at the Santa Monica Pier in California.

This is the historic direction of the “Mother Road.”

Why Start Route 66 in Chicago?

Chicago is the official beginning of Route 66. There’s something powerful about standing at the historic Route 66 sign downtown and knowing you’re about to cross America.

Starting in Chicago offers:

• A symbolic and emotional kickoff
• Great international flight connections
• An iconic American city experience before hitting the road
• A gradual transition from city to open landscapes

Spending 1–2 days in Chicago before starting your drive is highly recommended.

Why Finish Route 66 in Santa Monica?

Ending your Route 66 road trip at the Santa Monica Pier feels cinematic.

The “End of the Trail” sign marks the symbolic completion of the journey. Reaching the Pacific Ocean after days of driving through small towns, deserts, and historic highways creates a strong emotional payoff.

The landscapes also build beautifully in this direction:

• Midwest farmland
• Oklahoma plains
• New Mexico deserts
• Arizona red rocks
• California coastline

Driving east to west gives you a natural scenic crescendo.

East to West: The Emotional Build-Up

Driving Route 66 from Chicago to Santa Monica offers:

Pros:

• Landscapes become more dramatic each day
• Strong psychological sense of progression
• The Pacific Ocean as a grand finale

Cons:

• International travelers may start with jet lag
• Navigating Chicago traffic on Day 1

For first-time Route 66 travelers, this direction usually feels the most rewarding.

Driving Route 66 West to East (Santa Monica to Chicago)

Some travelers prefer starting in Los Angeles and driving toward Chicago.

Why Start in Santa Monica?

Starting in California can feel easier logistically:

• Warm weather from day one
• Easy car rental options
• Possible cheaper flights depending on season

You immediately begin with dramatic desert landscapes and Arizona highlights.

The Downside of West to East

While completely doable, this direction changes the emotional rhythm of the trip.

Instead of building toward dramatic scenery, the landscapes become flatter as you approach Illinois.

Finishing in Chicago is still great — but it doesn’t have the same “end-of-the-road” feeling as touching the Pacific Ocean.

For some travelers, that emotional finish matters more than they expect.

What If You Don’t Have Time for the Full Route?

Not everyone has 14 days for a full Route 66 road trip. The good news is you can still experience the classic Route 66 highlights with a partial route.

Popular Shorter Route 66 Options

Chicago to Santa Fe

Great mix of Midwest charm and Southwest culture.
Works well for a 7–10 day itinerary.

Amarillo to Los Angeles

Focuses on the most scenic western sections, including Arizona’s iconic towns.

Arizona & California Only

If you want dramatic desert landscapes, this is the most visually intense stretch.

You don’t need to drive every mile of Route 66 to feel like you’ve experienced it.

What Should Influence Your Start and Finish Decision?

Here’s what actually matters when choosing where to start Route 66:

1️⃣ Time Available

• 7 days → partial Route 66
• 10–14 days → full classic route
• 20+ days → slower, deeper exploration

2️⃣ Flight Prices

Sometimes, the cheapest flight combination should guide your decision. One-way car rental fees can also impact your budget.

3️⃣ Travel Style

Traveling with friends? A clear emotional build toward Santa Monica often keeps energy high.

Traveling as a couple? Either direction works well — pacing matters more.

4️⃣ Landscape Preference

Do you want a gradual build in scenery?
Choose Chicago to Santa Monica.

Want immediate dramatic landscapes?
Start in California.

My Honest Recommendation (Based on Experience)

If this is your first Route 66 road trip, drive:

👉 Chicago to Santa Monica

It feels iconic.
It feels complete.
It builds beautifully.

If you have limited time, focus on the western half of Route 66 — especially Arizona and California.

There’s no wrong direction. But there is a direction that feels more emotionally satisfying.

Common Route 66 Planning Mistakes

Avoid these:

• Trying to drive the full Route 66 in 7 days
• Ignoring one-way rental fees
• Underestimating Chicago or LA traffic
• Planning equal time per state
• Overcomplicating daily routing

Choosing the right start and finish point is step one. Structuring your daily drive is what makes the trip smooth.

Plan Your Route 66 the Smart Way 🗺️

Whether you start in Chicago, Santa Monica, or somewhere in between, the real challenge isn’t the direction — it’s knowing:

• Which historic alignments to follow

• Which towns are worth overnight stays

• How to pace the days realistically

• Where to stop for iconic Route 66 highlights

That’s exactly why I created the Route 66 RoadBook.

It’s designed to work for both classic full-route trips and shorter variations.

What’s included:

✅ Day-by-day Route 66 itinerary
✅ Clear routing for historic alignments
✅ Logical overnight towns
✅ Must-see stops + hidden gems
✅ Google Maps integration
✅ Instant PDF — use it offline

Trusted by 10,000+ travelers exploring Route 66

👉 Explore the Route 66 RoadBook

Make your Route 66 road trip unforgettable — not overwhelming.