Route 66 - Eastbound
Santa Monica to Chicago
Experience the ultimate Route 66 journey on this fully guided 12-day eastbound adventure from Santa Monica to Chicago, tracing the most iconic highway in American history from end to end. Beginning at the Santa Monica Pier—the official western terminus of Route 66—and concluding in downtown Chicago, this immersive tour brings the story of the Mother Road to life through classic towns, legendary landmarks, unforgettable landscapes, and living Americana.
Designed for travelers who want more than just a drive, this small-group Route 66 tour blends historic Route 66 segments with cultural highlights, scenic byways, and meaningful local experiences. Along the way, you’ll explore famous Route 66 cities and hidden gems across California, Arizona, New Mexico, Texas, Oklahoma, Kansas, Missouri, and Illinois, traveling through ever-changing scenery—from Mojave Desert highways and Painted Desert vistas to prairie towns, river valleys, and urban skylines.
Highlights include Hollywood and Beverly Hills, ghost towns like Oatman, the longest preserved stretch of original Route 66 in Arizona, Petrified Forest National Park, Cadillac Ranch, the Oklahoma Route 66 Museum, Meramec Caverns, the Gateway Arch in St. Louis, Abraham Lincoln’s Springfield, and the official eastern endpoint of Route 66 in Chicago. You’ll dine at classic Route 66 restaurants, visit historic motels and museums, and meet the people who continue to preserve the legacy of America’s Main Street.
Traveling eastbound allows you to experience Route 66 as many early travelers once did—following opportunity, history, and adventure across the country. With expert tour management, thoughtfully selected hotels, included meals and attractions, and plenty of time to explore, this journey offers a relaxed yet comprehensive way to experience the full story of Route 66.
Whether you’re a lifelong Route 66 enthusiast or discovering the Mother Road for the first time, this tour delivers a rich blend of history, nostalgia, culture, and classic American road trip spirit—all without the stress of planning or driving.
2026 Tour Pricing
$6,249.00 Per Person Double Occupancy
$7,399.00 Per Person Single Occupancy
$5,899.00 Per Person Triple Occupancy
$5,799.00 Per Person Quad Occupancy
Tour Details:
Inclusions:
- Professional Tour Guide
- Mercedes Benz Sprinter Van
- 11 nights hotel accommodations
- 11 breakfasts, 5 lunches, 6 dinners
- Afternoon Architecture River Cruise in Chicago
- Abraham Lincoln Presidential Library & Museum
- Gateway Arch
- Meramec Caverns
- Tour of the Coleman Theater
- First American’s Museum
- Oklahoma City Memorial
- Route 66 Interpretive Center, Chandler, OK
- Petrified Forest National Park
- Tour of Hollywood & Beverly Hills
- Gratuities for included meals
- Airport Transfers
- Park Entrance Fees
- Applicable Taxes and Fees
Exclusions:
- Airfare
- Any meals not listed
- Alcoholic drinks
- Items of a personal nature
- Gratuities for the Southwest Adventure Tours guide and included activities
Requirements:
Clients should be comfortable walking on uneven terrain for an average of 1 to 3 miles at a time. Elevation gain and loss averages between 50 to 300 ft over the course of the areas visited during this tour. Touring and overnight locations are above 6000 to 8000 ft above sea level in some areas
Arrival Location: Los Angeles International Airport – LAX
Arrival Time: By 2:00 PM Pacific Standard Time
Departure Location: Chicago O’Hare ORD or Chicago Midway Airport MDW
Departure Time: Any time after 7:00 AM on Day 12
Itinerary:
Day 1: Arrival & Santa Monica – The Journey Begins
Your eastbound adventure along Historic Route 66 starts where the land meets the sea. Day 1 is dedicated to seamless arrivals, iconic landmarks, and the first of many shared memories with your travel group.
Morning & Afternoon: Arrival & Seamless Transfers
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Arrival Hub: Los Angeles International Airport (LAX) to Santa Monica, CA.
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Arrival Window: Please ensure your flight arrives no later than 2:00 PM PST.
Late Afternoon: The Western Terminus
We gather at the Santa Monica Pier, the official western terminus of America’s Main Street.
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Explore at Leisure: Take in the sights of the historic boardwalk, the Pacific Wheel, and the "End of the Trail" sign.
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Photography Opportunity: Capture the iconic Route 66 signage with the Pacific Ocean as your backdrop—the perfect "start" photo for your 12-day gallery.
Evening: Welcome Dinner & Sunset
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Kick-off Celebration: Meet your fellow travelers and guides over a curated Welcome Dinner. This is the perfect time to review the 12-day itinerary and ask your tour leader any questions.
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The Pacific Sunset: We recommend lingering on the pier to watch the sun dip below the horizon. It’s a nostalgic, peaceful start to a journey that will take you 2,448 miles across the American landscape.
Lodging: Hampton Inn & Suites by Hilton Santa Monica
Meals Covered: Dinner
Day 2: Hollywood Highlights & The Gateway to the Mojave
Start your morning with a hearty breakfast and perhaps a final, refreshing stroll along the Santa Monica shoreline before we head inland. The day’s adventure kicks off with a comprehensive tour through the glitz and glamour of Hollywood, West Hollywood, and Beverly Hills. You will see the world-famous Hollywood Sign and stroll along the Walk of Fame, passing the Dolby Theatre and the historic Chinese Theatre. We’ll cruise the legendary Sunset Strip, pass the iconic Laugh Factory, and view the luxury estates of Beverly Hills and the high-fashion boutiques of Rodeo Drive. Along the way, we’ll point out famous filming locations and visit the original 1926 western terminus of Route 66, marking our official transition from the coast to the highway.
Following the city tour, enjoy a leisurely lunch at one of Los Angeles' many local eateries. In the afternoon, the scenery shifts from the urban sprawl to the rugged beauty of the San Bernardino Valley. We’ll travel through San Bernardino and Victorville, climbing toward the high desert as we make our way to Barstow, California. Upon arrival this evening, the group will gather for dinner at a local restaurant to relax and recount the day’s sights before settling in for our overnight stay at the gateway to the Mojave Desert.
Lodging: Holiday Inn & Suites Barstow
Meals Covered: Breakfast, Dinner
Day 3: Vintage Americana: Traversing Arizona’s Longest Original Stretch
The third day of our journey offers a breathtaking scenic drive across the Mojave Desert, a landscape defined by its vast horizons and rugged beauty. Our first stop is Needles, California, before we cross the state line into the historic mining ghost town of Oatman, Arizona. Nestled at an elevation of 2,700 feet along one of the most adventurous mountain stretches of the original Mother Road, Oatman is a lively and quirky destination. You'll have time to explore its unique gift shops, grab a snack at a local eatery, and perhaps meet the town's famous residents, the wild burros that roam the streets.
Leaving the mountains behind, we continue through picturesque desert landscapes to Kingman, Arizona, for a nostalgic included lunch at the iconic Mr. D’z Route 66 Diner or another beloved local landmark. After refueling, we embark on a drive along the longest remaining continuous stretch of the original Route 66. This evocative section of the highway takes us through classic stops like Peach Springs and Hackberry, where the spirit of the 1950s is still very much alive in the vintage neon and roadside memorabilia.
Our afternoon culminates in Seligman, famously heralded as the “Birthplace of Historic Route 66.” It was here that local barber Angel Delgadillo and his community fought to preserve the road’s legacy after it was bypassed by Interstate 40 in 1978. Their efforts sparked the global movement to revitalize the Mother Road, making this a sacred site for any road trip enthusiast. We conclude the day’s exploration in Williams, Arizona, where you can enjoy a sunset stroll along its beautifully preserved main street and find a local spot for dinner. Finally, we head into the cool pines of Flagstaff, Arizona, for our overnight stay.
Lodging: Little America Hotel (Flagstaff)
Meals Covered: Breakfast, Lunch
Day 4: Painted Deserts & The Land of Enchantment
Your morning begins with a dramatic environmental shift as we descend from the high-altitude ponderosa pine forests of Flagstaff into the rugged, sun-drenched high desert. Our first destination is the nostalgic town of Winslow, Arizona, a quintessential Route 66 stop immortalized in American pop culture. After taking time to "stand on the corner" and soak in the mid-century charm, we continue eastward into the prehistoric wonders of Petrified Forest National Park. Here, we’ll enjoy an included lunch followed by a stunning drive through the Painted Desert and along Blue Mesa. You’ll have ample opportunities for photography before we take a guided walk through the Rainbow Forest, marveling at the ancient, crystallized logs that define this unique landscape.
As we cross the state line into New Mexico—the "Land of Enchantment"—the journey follows the historic ribbons of the Mother Road to Gallup. We’ll pause at the legendary El Rancho Hotel, a beautifully preserved 1930s landmark that once served as the desert home for Hollywood’s biggest stars during the golden age of Western cinema. Its rustic elegance and rich history offer a perfect glimpse into the era when Route 66 was the premier gateway to the West.
We conclude the day’s journey in Albuquerque, where the evening is yours to discover the soul of the city in its Historic Old Town. This area remains the heart of Albuquerque, featuring narrow cobblestone streets and centuries-old adobe architecture. You can spend your night browsing boutique shops for authentic turquoise jewelry and hand-woven rugs or dining on world-class New Mexican cuisine. Be sure to try the local enchiladas and honey-drizzled sopaipillas in the shadow of the 18th-century San Felipe de Neri Church, a peaceful end to a day of desert discovery.
Lodging: Hilton Garden Inn ABQ Uptown
Meals Covered: Breakfast, Lunch
Day 5: High Desert Heights & Texas Panhandle Icons
Our morning kicks off with a journey north along a scenic stretch of the original Route 66, climbing toward the artistic heart of the Southwest: Santa Fe, New Mexico. You’ll have time to immerse yourself in this historic capital’s unique blend of Anglo, Spanish, and Native American cultures. Highlights include a visit to the legendary La Fonda on the Plaza, a landmark hotel that has hosted travelers for centuries. After soaking in the adobe charm of the plaza, we continue eastward to Santa Rosa for a brief midday pause before heading into Tucumcari. This town is a living time capsule of Route 66 nostalgia, where we’ll see the neon glow of the Blue Swallow Motel, the whimsical architecture of Tee Pee Curios, and the striking Mother Road monument.
After an included lunch stop, we cross the state line into the vast horizons of the Texas Panhandle. Our first stop is a milestone moment at the Route 66 Midpoint in Adrian, the exact mathematical center between Los Angeles and Chicago—the perfect spot for a commemorative photo. From there, we proceed toward Amarillo for a visit to one of the world’s most famous roadside art installations: Cadillac Ranch. This quirky masterpiece features ten vintage Cadillacs buried nose-first in the soil, their iconic tail fins rising toward the Texas sky. Whether you're an art lover or a car enthusiast, this "interactive" monument is a must-see staple of the American road trip.
We conclude our day in Amarillo with a quintessential Lone Star State celebration. After checking into the hotel, the group will gather for a legendary dinner at The Big Texan Steak Ranch. Known worldwide for its massive steaks and hospitable Texas atmosphere, it provides the perfect, high-energy backdrop to toast to the first half of our cross-country expedition.
Lodging: Drury Inn & Suites
Meals Covered: Breakfast, Lunch
Day 6: Exploring the Heart of Oklahoma
We begin our morning with a few final highlights in Amarillo before waving goodbye to the Texas Panhandle and crossing into Oklahoma. Our first stop is the tiny, eccentric town of Erick, home to some of the most colorful characters and quirky roadside attractions on the entire Mother Road. This stop perfectly captures the "Old West" spirit and rural charm that defined the early days of highway travel.
The journey continues to Clinton for an immersive visit to the Oklahoma Route 66 Museum. Widely considered one of the best along the entire route, this museum offers a decade-by-decade journey through the history of the highway. From the dust bowl era to the neon-soaked golden age of the 1950s, you’ll discover the personal stories, music, and labor that transformed this stretch of pavement into a national legend. After exploring the exhibits, enjoy a leisurely lunch on your own in this eclectic community before we press on toward the state capital.
Upon arriving in Oklahoma City, we shift our focus to a vital and deeply moving part of the American story at the First Americans Museum. This world-class facility, which opened in 2021, honors the diverse histories and vibrant cultures of the 39 First American Nations in Oklahoma. It provides a meaningful look at the land's original inhabitants, offering a perspective that enriches the narrative of the road we travel. We conclude our day in the heart of Bricktown, the city's premier entertainment district. The evening is yours to explore the scenic canal, enjoy live music, and choose from a variety of local restaurants for dinner.
Lodging: Hampton Inn & Suites Oklahoma City-Bricktown
Meals Covered: Breakfast, Lunch
The Mother Road’s Architects: The Icons of Route 66 Oklahoma
The morning begins with a powerful and reflective visit to the Oklahoma City National Memorial. This beautifully designed sanctuary honors the victims, survivors, and rescuers of the tragic April 19, 1995 bombing, offering a peaceful moment of remembrance before we head back out onto the highway. Turning our compass north toward Tulsa, our first roadside stop is POPS in Arcadia—a modern Route 66 icon famous for its giant, neon soda bottle and a dizzying collection of over 600 soda varieties. Just down the road, we’ll pause at the Arcadia Round Barn, a masterfully restored 1898 architectural marvel that stands as one of the most photographed landmarks on the entire trail.
As we journey into Chandler, the history of the highway comes alive at the Route 66 Interpretive Center. Here, you’ll take a nostalgic, high-tech "drive" through the decades, tracing the road’s evolution from dust-bowl escape route to the "Mother Road" immortalized by John Steinbeck. While in town, we will also step inside McJerry’s Route 66 Gallery to meet Jerry McClanahan, an acclaimed artist and foremost historian whose passion has helped preserve the highway's legacy for modern adventurers.
After a late, authentic lunch at the legendary Rock Café in Stroud—a local staple built from local sandstone in 1939—we travel to Sapulpa for an exclusive look inside Gasoline Alley Classics, a treasure trove of vintage auto memorabilia. We wrap up our deep dive into Oklahoma's highway heritage in Tulsa, stopping at the Route 66 Historical Village and the Cyrus Avery Centennial Plaza. Dedicated to the man who championed the creation of the highway, this plaza is a fitting tribute to the "Father of Route 66." The evening is yours to relax and explore Tulsa's thriving arts and dining scene.
Lodging: Embassy Suites Tulsa, Ok
Meals Covered: Breakfast, Lunch
Day 8: Three States, Two Giants, and a Touch of Hollywood
Our morning begins as we wave goodbye to Tulsa and journey toward the historic town of Miami, Oklahoma, for a tour of the spectacular Coleman Theatre. This beautifully restored 1929 vaudeville theater offers a glamorous glimpse into the entertainment golden age that greeted early highway travelers. As we continue along this rich stretch of pavement, we will visit two of the most beloved and eccentric roadside monuments in America: the towering folk art masterpiece at Ed Galloway’s Totem Pole Park and the wonderfully whimsical Blue Whale of Catoosa, a nostalgic waterfront icon that has brought smiles to road-trippers for generations.
The route then takes us on a short but memorable crossing through the southeast corner of Kansas. Here, we’ll pause for photos at Cars on the Route in Galena—a vintage service station famous for inspiring the beloved characters of Pixar's Cars—before admiring the historic Rainbow Bridge, the last remaining single-span Marsh arch bridge on the entire highway.
After a midday break, we cross into the rolling hills of Missouri for a full afternoon of pure Route 66 nostalgia. We’ll wind our way through classic highway towns like Joplin, Carthage, Avilla, and Spencer, and stop at Gary’s Gay Parita, a meticulously recreated 1930s Sinclair gas station that captures the quintessential spirit of roadside hospitality. We wrap up this unforgettable day of exploration in Springfield, Missouri, proudly recognized as the birthplace of the Route 66 name. To celebrate our journey through three distinct states, the group will gather for a premium dinner at the renowned Jimm’s Steakhouse before settling in for a relaxing evening.
Lodging: Hampton Inn & Suites Springfield
Meals Covered: Breakfast, Dinner
Day 9: The Show-Me State: Caves, Colossal Chairs, and the Gateway to the West
Our morning kicks off with a collection of classic roadside marvels along the Missouri Route 66 corridor. We begin with a must-see photo opportunity at the world-famous Route 66 Giant Rocking Chair, followed by a stop at Route 66 Motors in Rolla to admire some vintage American horsepower. From there, we cruise into the historic town of Cuba, Missouri. Known affectionately as "Route 66 Mural City," you’ll have plenty of time to stretch your legs, explore the town's 14 vibrant outdoor murals depicting local and highway history, and soak up the small-town charm at your own pace.
After a midday break for lunch, we trade the pavement for a journey underground at one of the most famous stops in road trip history: Meramec Caverns. Hidden beneath the rolling hills of the Meramec Valley, this extensive limestone cavern system is legendary for its spectacular, colorful mineral formations. A guided tour will take you through these massive subterranean rooms while revealing the fascinating geology and local lore—including tales of Jesse James using the caves as a hideout.
Emerging back into the sunshine, we make our way into St. Louis, Missouri. In the late afternoon, we will visit the city's crowning achievement: the Gateway Arch. You’ll climb aboard the unique tram system for an engineering adventure to the very top of the 630-foot monument, rewarding you with breathtaking panoramic views of the city skyline and the sweeping Mississippi River. The evening is yours to enjoy the best of downtown St. Louis. Wander through the beautifully revitalized historic Union Station, catch the energy outside Busch Stadium, or take a sunset stroll along the scenic riverfront.
Lodging: Drury Plaza Hotel St. Louis At The Arch
Meals Covered: Breakfast
Day 10: Presidents and Pioneers: Crossing the Mississippi to Lincoln’s Homeland
Our morning begins with a spectacular photo opportunity at the historic Chain of Rocks Bridge. Famous for its dramatic 22-degree bend in the middle of the river, this legendary crossing offers a stunning, distant view of the Gateway Arch framing the Mississippi River behind us. From there, we officially enter Illinois, following the old highway as it winds through a collection of charming, quintessential Route 66 communities. We’ll make nostalgic stops through the historic streets of Litchfield, Girard, Virden, and Auburn, tracing the classic paths of early American motorists.
In the afternoon, our focus shifts to the remarkable legacy of America's 16th president as we arrive in Springfield, Illinois. We will visit the world-class Abraham Lincoln Presidential Library & Museum, an immersive facility that masterfully documents Lincoln’s life, his presidency, and the high-stakes history of the American Civil War. Following our time at the museum, we will view Lincoln’s beautifully preserved neighborhood home, gaining an intimate glimpse into his life before he changed the course of a nation.
After checking into the hotel and settling in for the evening, the group will gather for a fun and exceptionally tasty piece of roadside history. We’ll head over to the legendary Cozy Dog Drive-In, officially recognized as the birthplace of the corn dog. Enjoying a basket of "Cozy Dogs" surrounded by decades of vintage highway memorabilia is the absolute perfect way to wrap up a day dedicated to great American legends.
Lodging: May Departure - Holiday Inn Express Springfield, IL
June Departure - Drury Inn & Suites Springfield, IL
Meals Covered: Breakfast, Lunch, & Dinner
Day 11: Historic Stations, Deep Dish, and Chicago’s Radiant Skyline
Our morning begins with a brief driving tour of the remaining Route 66 gems in Springfield before we set our sights north toward the end of the trail. We’ll wind through the historic Illinois prairie, making nostalgic stops in the classic highway towns of Lincoln, Normal, and Towanda. Midday brings us to the vibrant community of Pontiac, where we’ll visit the Route 66 Association of Illinois Museum, a treasure trove of vintage memorabilia, retro camper vans, and historical preservation exhibits. You’ll have plenty of time to explore the museum and enjoy lunch on your own at a local downtown café.
In the afternoon, we embark on the official home stretch toward the Windy City, pausing to admire two beautifully preserved relics of roadside history: the 1932 cabin-style Standard Oil Station in Odell and the historic Ambler’s Texaco Station in Dwight. These iconic stops offer a final, vivid glimpse into the golden era of full-service highway travel. As the rural landscapes give way to the soaring Chicago skyline, we will enjoy a drive-by view of the majestic Willis Tower before heading to the intersection of Adams Street and Michigan Avenue. Here, we'll capture our official group photos at the historic Route 66 End Sign, marking the completion of our epic cross-country expedition.
To celebrate our journey, the group will gather for an authentic Chicago-style deep-dish pizza dinner at a beloved local pizzeria. We will then cap off this unforgettable 12-day adventure with a spectacular Evening Architecture River Cruise. Gliding down the Chicago River as the city lights illuminate the towering skyscrapers, you’ll watch the urban landscape transform under the night sky—a serene, world-class finale to your legendary journey along the Mother Road.
Lodging: Radisson Blu Aqua Hotel, Chicago
Meals Covered: Breakfast, Dinner
Day 12: Farewell to the Windy City & The Mother Road
After a final breakfast in Chicago, our unforgettable cross-country journey along Historic Route 66 officially draws to a close. Today, you will depart the Windy City carrying a lifetime of memories, stories, and friendships formed along the 2,448 miles of America’s Main Street.
To ensure your journey home is completely stress-free, your individual departure logistics will be handled for you. Complimentary airport transfers to both Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) will be scheduled in advance based on your specific flight itinerary. When booking your return travel, please select flights that depart no earlier than 7:00 AM from either airport to allow ample time for your transfer and check-in. Whether you are heading back home or extending your stay to explore more of Chicago's world-class museums and lakefront, we wish you safe travels and look forward to welcoming you on another historic adventure soon!
Meals Covered: Breakfast
SWAT Trip Protection Plan (TPP)
Travel with Confidence. Cancel with Flexibility.
The SWAT Trip Protection Plan (TPP) gives you the freedom to cancel your tour for any reason up to the day before departure and receive a full refund of your SWAT-collected tour payments. It’s a simple, transparent cancellation waiver designed to provide flexibility for our guests and clarity in our booking process.
What TPP is-and Isn't
- Not Insurance. It is SWAT's own cancellation waiver.
- Coverage: Full refund of Swat-collected tour price and SWAT-sold add-ons (e.g., optional activities, additional nights of lodging, etc).
Who & What's Eligible
- Who: Any named traveler on a SWAT booking (direct or qualifing agency/partner sale).
- When: Must be added at initial checkout (cannot be added later).
- Exclusions:
- Cruise or third-party products (e.g., AMA Waterways) outside SWAT's control.
- Air or rail tickets not booked by SWAT
- Government fees (e.g., park passes).
- Wholesale agreements that prohibit supplier waivers.
How to Purchase
- At checkout, you'll see an unchecked box offering TPP at 10% of your SWAT cart total.
- Check the box to add TPP; leave it unchecked to decline.
- Once you leave the checkout page, you cannot add or remove TPP.
Cancelling Under TPP
- Deadline: You may cancel through 11:59 pm local time in your tour's start city on the day before your first activity.
- Process:
- Call or email the contact on your confirmation notice.
- We'll log your request timestamp (with time zone) and ask for a brief written confirmation via email to info@southwestadventuretours.com.
- Refunds: We refund 100% of all SWAT-collected tour and SWAT add-on amounts. The 10% TPP fee is retained.
After the Deadline
- If you cancel on or after your tour start date, or are a no-show, SWAT cancellation terms apply (no refund of tour amounts).
Rescheduling
- You may reschedule your protected booking once within 12 months of your original departure date at no additional TPP fee.
- If your new tour price is higher you pay only the difference in TPP fee; if lower, there will be no refund of the original fee.
Timing of Refund
- Once we receive your written cancellation request, Accounting initiates your refund within 5-7 business days.
- Actual bank posting time depends on your bank's processing schedule.
FAQ
What does TPP cover?
SWAT-collected tour and SWAT-sold add-on payments only.
When must I buy?
At initial checkout, cannot add later.
Can I cancel for any reason?
Yes, up to the day before your tour starts.
Is TPP refundable?
No, the 10% fee never refunds.
Can I move my trip?
Yes, once within 12 months at no extra TPP fee.
By choosing SWAT Trip Protection Plan, you gain flexibility to cancel worry-free, while SWAT maintains clear, consistent operations and revenue handling. Enjoy your adventure with confidence!