The Ultimate Route 66 Road Trip Itinerary: A Journey Through America’s Historic Heart

Few journeys capture the spirit of freedom and adventure quite like the iconic Route 66 road trip. Known as the “Main Street of America,” Route 66 stretches from Chicago, Illinois, to Santa Monica, California, covering nearly 2,448 miles (3,940 km) across eight states. This legendary highway passes through small towns, vast deserts, and vibrant cities, offering a nostalgic glimpse into mid-20th-century Americana. Whether you’re a history enthusiast, a photography lover, or an adventure seeker, Route 66 delivers a once-in-a-lifetime travel experience filled with diners, neon lights, and breathtaking scenery.

Route 66 runs through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, blending rural charm with urban energy. Although the original route was decommissioned in 1985, most of it remains drivable and well-marked, featuring numerous attractions that preserve the old spirit of the open road.

Total distance: 2,448 miles
Ideal duration: 2–3 weeks
Best travel season: Late spring to early autumn (May–October)

Day 1–2: Chicago, Illinois – The Starting Point

Begin your adventure in Chicago, where Route 66 officially starts at Adams Street. Explore the Willis Tower Skydeck, Millennium Park, and enjoy a deep-dish pizza before hitting the road.

Where to stay:

• Budget: HI Chicago Hostel (~$50/night)
• Mid-range: Hampton Inn Downtown (~$150/night)
• Luxury: The Langham (~$350/night)

Food highlights: Chicago-style pizza at Lou Malnati’s or hot dogs at Portillo’s.

Estimated daily expense: $150–$250

Drive 300 miles southwest to St. Louis, crossing the Chain of Rocks Bridge, an iconic Route 66 landmark. Don’t miss the Gateway Arch, the tallest monument in the U.S.

Top attractions:

• Gateway Arch National Park
• Route 66 State Park
• Ted Drewes Frozen Custard (a local favorite)

Where to stay:

• Budget: Red Roof Inn (~$60/night)
• Mid-range: Drury Plaza Hotel (~$140/night)

Estimated daily expense: $130–$200

Kansas only claims 13 miles of Route 66, but it’s packed with charm. Stop in Galena to see “Tow Tater,” the tow truck that inspired Mater from Pixar’s Cars.

Attractions:

• Old Riverton Store
• Galena Mining & Historical Museum

Estimated daily expense: $100

Oklahoma holds the longest stretch of Route 66. Enjoy vintage gas stations, retro diners, and quirky museums.

Top attractions:

• Blue Whale of Catoosa
• Route 66 Museum in Clinton
• Oklahoma City National Memorial

Food highlights: Chicken-fried steak at Ann’s Chicken Fry House.

Where to stay:

• Budget: Super 8 (~$70/night)
• Mid-range: 21c Museum Hotel (~$160/night)

Estimated daily expense: $130–$220

In the Texas Panhandle, Amarillo greets travelers with cowboy spirit and classic roadside Americana.

Must-see attractions:

• Cadillac Ranch (spray-paint your own car!)
• Big Texan Steak Ranch (famous 72-oz steak challenge)

Where to stay:

• Budget: Days Inn (~$70/night)
• Mid-range: Courtyard by Marriott (~$130/night)

Estimated daily expense: $120–$200

Travel west to Santa Fe, known for its adobe architecture and artistic culture, then onward to Albuquerque.

Top attractions:

• Old Town Albuquerque
• Sandia Peak Tramway
• Santa Fe Plaza and art galleries

Food highlights: Try green chile stew or enchiladas with red chile.

Where to stay:

• Budget: Motel 6 (~$70/night)
• Mid-range: Hotel Albuquerque (~$150/night)

Estimated daily expense: $130–$210

As you enter Arizona, the landscape transforms into red rocks and pine forests. Stop in Flagstaff, a charming mountain town, and take a detour to the Grand Canyon (only 80 miles north).

Top attractions:

• Meteor Crater
• Standin’ on the Corner Park in Winslow
• Grand Canyon National Park

Food highlights: Local craft beer at Beaver Street Brewery.

Where to stay:

• Budget: Econo Lodge (~$90/night)
• Mid-range: Little America Hotel (~$160/night)

Estimated daily expense: $150–$250

This section of Route 66 is filled with nostalgia—old motels, retro gas stations, and neon signs that feel frozen in time.

Top attractions:

• Route 66 Museum in Kingman
• Delgadillo’s Snow Cap Drive-In in Seligman

Estimated daily expense: $120–$180

Cross into California’s Mojave Desert—scenic yet harsh terrain. Stop at the Route 66 Mother Road Museum in Barstow and admire the desert landscapes.

Where to stay:

• Budget: Motel 6 (~$80/night)
• Mid-range: Best Western Desert Villa (~$130/night)

Estimated daily expense: $130–$200

Your final stop is Santa Monica Pier, where the famous “End of the Trail” sign marks the completion of Route 66. Spend your last day relaxing on the beach, exploring the pier, or visiting nearby Los Angeles attractions like Hollywood or Beverly Hills.

Where to stay:

• Budget: HI Santa Monica Hostel (~$60/night)
• Mid-range: Shore Hotel (~$250/night)
• Luxury: Fairmont Miramar (~$450/night)

Food highlights: Seafood at The Lobster or tacos at Blue Plate Taco.

Estimated daily expense: $200–$350

• Fuel: $400–$700 (depending on vehicle)
• Accommodation (average): $1,500–$2,500 for 18–20 nights
• Food & drinks: $700–$1,200
• Attractions & activities: $300–$500
• Total Estimated Budget: $2,900–$4,800 per person for the full Route 66 trip

• Vehicle check: Ensure your car is in excellent condition; Route 66 has long stretches with minimal services.
• Weather caution: Summers can be extremely hot, especially in Texas, New Mexico, and Arizona. Carry water, sunscreen, and a first-aid kit.
• Accommodation: Pre-book hotels during peak seasons (May–August).
• Navigation: Download offline maps—some areas lack mobile coverage.
• Local laws: Speed limits vary by state; always follow posted signs.
• Safety: Avoid driving at night in rural stretches, and always refuel before entering desert areas.

Conclusion

A Route 66 road trip is not just a drive—it’s an exploration of American culture, history, and landscapes. From the skyscrapers of Chicago to the beaches of Santa Monica, every mile reveals stories of a bygone era preserved in roadside diners, motels, and neon lights. Whether you’re chasing nostalgia, adventure, or pure scenic beauty, Route 66 promises an unforgettable experience that truly captures the essence of the open road.