Route 66 From Chicago to LA

Arrive in Chicago, where you'll be met and transferred to our hotel in the heart of the city. Please plan to arrive by 14:00 at the latest. Once you’ve had a chance to unwind, we begin our adventure with a leisurely Architecture River Cruise through the downtown.

As the afternoon light begins to fade, the city’s iconic skyline takes on a warm, dramatic glow. In the evening, gather with the group for an included welcome dinner and a true Chicago experience - deep dish pizza at a popular local spot like Giordano’s or The Exchequer. Wrap up the day with a walk to the official starting point of Route 66, where you can snap a few photos at the famous "Begin" sign - an unforgettable first step on your journey west.

Please note: This tour involves extensive hiking on uneven terrain, covering an average of 5 to 8 kilometres at a time, but sometimes more. Elevation changes range from 50 to 1,000 feet, and both touring and overnight locations are situated at altitudes between 5,000 and 8,000 feet above sea level. Due to the physical demands of this itinerary, participants should be prepared for significant activity.

Chicago - Dwight - Odell - Pontiac - Springfield, IL. Start today with a drive past the Willis Tower before stopping just blocks from the Route 66 starting point at Lou Mitchell’s - long considered the “first stop on the Mother Road.” Savour a traditional American diner breakfast, featuring fluffy pancakes, Belgian waffles, creamy shakes, and what their iconic neon sign boasts as “the world’s finest coffee.”

From here, we head out of Chicago and hit the open road, travelling along stretches of the original Route 66 whenever possible. Key stops along the way include the restored Ambler’s Texaco Station in Dwight, the historic Standard Oil Station in Odell, and a visit to the Route 66 Association of Illinois Museum in Pontiac.

Enjoy some free time for lunch before we continue through charming Route 66 towns like Towanda, Normal, and Lincoln. On arrival in Springfield, check into the hotel and gather with the group for a nostalgic dinner at Cozy Dog Drive-In - the birthplace of the corn dog and a true Route 66 icon.

Springfield - St Louis. We begin today with a visit to the Abraham Lincoln Presidential Library & Museum, where immersive exhibits trace the life of the 16th U.S. President and the pivotal events of the Civil War.

We’ll also stop at Lincoln’s former home before departing Springfield and continuing our journey towards St Louis, Missouri. Along the way, travel stretches of the original Route 66 through small-town gems like Auburn, Virden, Girard, and Litchfield.

A brief stop in Mt Olive is followed by a drive through Granite City and across the historic Chain of Rocks Bridge. By late afternoon, we arrive in St Louis and enjoy a visit to the Gateway Arch, including a tram ride offering sweeping views from the top. The evening is free for you to explore downtown St Louis - whether it’s the grand architecture of Union Station, the energy of Ballpark Village, or a peaceful stroll along the Mississippi River waterfront.

St Louis - Cuba - Springfield, MO. This morning, we continue west along the Old Road to one of Route 66’s most iconic attractions - Meramec Caverns. Hidden beneath the rolling hills of the Meramec Valley, this vast underground network features stunning mineral formations in a dazzling array of colours.

After a guided tour through the caverns, we head to the town of Cuba to discover its collection of 14 vibrant murals that celebrate local history and culture. The journey continues with quirky Route 66 stops including the world-famous Giant Rocking Chair, the oversized Giant Faucet, and a visit to the Route 66 Motors & Gift Shop in Rolla.

Arrive in Springfield, Missouri for an overnight stay and a hearty dinner at the beloved Jimm’s Steakhouse.

Springfield - Miami, OK - Tulsa. After breakfast, we set off from Springfield and continue our Route 66 journey with visits to classic Missouri stops like Gary’s Gay Parita, Spencer, Avilla, Carthage, and Joplin. From there, cross into Kansas for a quick photo opportunity at Cars on the Route in Galena, followed by a visit to the historic Marsh Arch Bridge.

Entering Oklahoma, we arrive in Miami (not that one!) to explore the beautifully restored Coleman Theater, a gem of Route 66 heritage. Continue on with visits to quirky roadside icons including Ed Galloway’s Totem Pole Park and the beloved Blue Whale of Catoosa.

Arriving in Tulsa, we enjoy time to explore the city's Route 66 highlights, including a visit to Cyrus Avery Plaza, honouring the man known as the Father of Route 66. Spend the evening soaking up the charm and history of this vibrant town.

Tulsa - Sapulpa - Davenport - Chandler - Oklahoma City. Start the morning with a visit to Tulsa’s Route 66 Historical Village, followed by a few more local landmarks. We then head further along the Mother Road. We reach Sapulpa for a guided tour of Gasoline Alley Classics and a stop at the iconic Rock Café.

After a brief visit in Davenport, we arrive in Chandler to explore the Route 66 Interpretive Center. This immersive experience takes you on a visual road trip through the decades, capturing the spirit of Route 66 from the 1920s to today. We'll also stop at McJerry’s Route 66 Gallery, home to an acclaimed artist and passionate historian of the road.

Next, we visit the Seaba Station Motorcycle Museum before continuing to Arcadia to see the famous Round Barn. Then it’s on to POPS, a colourful roadside favourite known for its towering soda bottle and a selection of over 600 sodas. Let a POPS soda expert help you pick a refreshing drink - be it an old-school classic or a fun new flavour.

Arriving in Oklahoma City, we cap off the afternoon with a visit to the First Americans Museum. Opened in 2021, this powerful cultural centre tells the stories of the 39 First American Nations in Oklahoma today, honouring their heritage and contributions - an essential part of Route 66 history. Later, we check in to our hotel in lively Bricktown, with the evening free to explore and dine at your leisure.

Oklahoma City - Clinton - Elk City - Amarillo. This morning, we enjoy touring of the Oklahoma City National Memorial which honours the victims, survivors, rescuers, and all who were affected by the Oklahoma City bombing on April 19, 1995. We then depart Oklahoma City and continue our Route 66 journey westward, first stopping in Clinton for lunch, followed by touring of the Oklahoma Route 66 Museum.

The museum offers a personal journey through the history of the nation’s most revered highway from a perspective of the state where it all began. Encounter the iconic ideas, images, and myths of the Mother Road. Learn about the dreams and the labour needed to make the road a reality. A bit further down the road in Elk City, we explore various sites and unique locations in this rural town.

Continue west to Amarillo, our destination for the day. After checking into our hotel, join the group for a true Texas experience at the Big Texan!

Amarillo - Adrian - Tucumcari - Santa Rosa - Santa Fe - Albuquerque. We leave Amarillo this morning and follow Route 66 west to one of its most iconic stops - Cadillac Ranch. Created by a group of San Francisco artists, this eccentric roadside attraction features ten vintage Cadillacs buried nose-down in the Texas plains, their tail fins angled to mimic the Great Pyramid of Giza. Continue to Adrian, TX, and pause at the official Route 66 halfway point - an ideal photo opportunity.

We cross into New Mexico and soak in the vintage Americana of Tucumcari. This classic Route 66 town is home to nostalgic landmarks like the Blue Swallow Motel, Tee Pee Curios, and La Cita Mexican Restaurant, all proudly preserving the spirit of the old road. Journey on to Santa Rosa, where we'll drive through town on historic Route 66 and stop for lunch at the colourful Joseph’s Bar & Grill.

From here, we follow the original route north into Santa Fe. Enjoy some time to explore the city’s charming downtown, rich in art, culture, and adobe architecture. Then continue to Albuquerque, where your evening is free to wander the historic Old Town. Meander through narrow streets lined with centuries-old adobe buildings, browse artisan shops offering jewellery, rugs, and pottery, and dine at local spots serving enchiladas and traditional sopaipillas. Be sure to visit the picturesque Old Town Plaza, framed by the 18th-century San Felipe de Neri Church.

Albuquerque - Gallup - Petrified Forest National Park - Winslow - Flagstaff. This morning, we set out from Albuquerque and continue west along the Mother Road, stopping in Gallup to visit the historic El Rancho Hotel. A cherished landmark from the 1930s, the hotel has hosted Hollywood stars and still exudes vintage charm.

Crossing into Arizona, we arrive at Petrified Forest National Park where you'll have time for lunch at your leisure before exploring the park’s striking landscapes. Take in the sweeping views of the Painted Desert and drive the scenic route through Blue Mesa, pausing for photos at key viewpoints. Then we stretch our legs with a walk through the Crystal Forest, where ancient, fossilized trees shimmer in the desert sun.

From there, we travel on to Winslow - immortalized by the Eagles' hit song - for a quick visit and a classic Route 66 photo op. Conclude the day in Flagstaff, where your evening is free to discover the lively, eclectic downtown.

Flagstaff - Seligman - Oatman - Barstow - San Bernardino. Just west of Flagstaff, the small town of Seligman, famously known as “The Birthplace of Historic Route 66”, is a must-visit for Route 66 fans. In 1972, Angel Delgadillo relocated his barber shop to the newly aligned Route 66 through Seligman, where business thrived until the town was bypassed by I-40 in 1978.

To boost tourism, Angel, his wife Vilma, and other local business owners formed the Historic Route 66 Association of Arizona. After exploring Seligman, we drive the longest stretch of the original Route 66, passing through towns like Peach Springs and Hackberry before reaching Kingman for lunch at Mr. D’z Route 66 Diner.

In the afternoon, we enjoy a scenic desert mountain drive to the historic ghost town of Oatman, perched at 2,700 feet. Oatman offers a nostalgic look at Route 66, complete with gift shops, restaurants, and wild burros roaming the streets. From here, we continue on through Needles, California, and arrive in Barstow to visit the Route 66 Mother Road Museum.

Conclude the day with dinner and an overnight stay at the quirky and historic Wigwam Motel in San Bernardino.

San Bernardino - Los Angeles - Santa Monica. After breakfast at a local diner, we head to Los Angeles for an exciting tour of Hollywood, West Hollywood, and Beverly Hills. Along the way, we'll see iconic sights like the Hollywood Sign, the Walk of Fame, Dolby Theatre, Laugh Factory, Sunset Strip, Rodeo Drive, Capitol Records, and the famous Chinese Theatre. The tour also includes glimpses of celebrity homes in Beverly Hills. We'll stop for lunch at a local diner (not included).

In the afternoon, we take a short drive to the Santa Monica Pier, home to the western terminus of Route 66. Enjoy some free time to explore the pier at your own pace. Later, join your fellow travellers for a farewell dinner on the pier, marking the perfect end to our unforgettable journey along America’s iconic Route 66.

Our tour comes to an end after breakfast and hotel check out. An included transfer takes you to the airport in Los Angeles for your onward flight.