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Home/USA/Historic Route 66

Ultimate Historic Route 66 Road Trip Adventures

Embark on the ultimate American road trip along the legendary Historic Route 66. Discover iconic roadside attractions, nostalgic neon-lit diners, and breathtaking landscapes that define the Mother Road. Whether you are seeking immersive historical guided tours, scenic sightseeing adventures, or cultural explorations, our curated experiences bring the spirit of mid-century Americana to life. From vintage charm to stunning natural wonders, unlock unforgettable memories on this world-famous highway. Book your journey today and experience the heart of American history!

4.78/5 avg ratingTours from $1407 unique experiencesFree cancellation available

At a glance

Tour Price

Tour Price

$322–$764 typical

Prices range from $140 to $1,350

Rating

Rating

4.78★ average

Based on 154 pooled reviews with 91% positive sentiment

Tour Length

Tour Length

4.5 hours median

Typical duration ranges from 2.3 to 10.2 hours

Tour Type

Tour Type

Sightseeing & Nature

57% of options focus on these themes

Languages

Languages

8 languages offered

Includes EN, DE, ES, FR, IT, JA, ZH, and KO

Booking Tip

Booking Tip

Book in advance

29% of tours are flagged likely to sell out

10 Products

Holiday Walking Tour: Underground Chicago via the Pedway

Holiday Walking Tour: Underground Chicago via the Pedway

3 hrsEco-FriendlyFree cancellationLikely to sell out
5 (27 reviews)
100%
0%
Excellentpassion for Chicago’s history and architecturepersonal and welcoming
Viator
$65
Book now
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Holiday Walking Tour: Underground Chicago via the Pedway
Summary

Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a to...

Inclusions
  • Transit tickets
  • Local expert guide
Exclusions
  • Food and beverages
Itinerary
  • Chicago Pedway
  • Chicago Cultural Center
  • Macy's on State Street
  • Block 37
  • Route 66
  • Cloud Gate
Good to know
  • Not recommended for travelers with spinal injuries, Not recommended for travelers with poor cardiovascular health, Public transportation options are available nearby, Travelers should have at least a moderate level of physical fitness, Should be able to climb stairs as not all train stations are equipped with elevators.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago Scenic Driving Tour

Chicago Scenic Driving Tour

2 hrsFree cancellation
5 (24 reviews)
98.2%
1.8%
10/10 recommendGreat tourawesome
Viator
$315
Book now
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Chicago Scenic Driving Tour
Summary

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you u...

Inclusions
  • Bottled Water
  • Private transportation
  • Free Hotel/Other Location Pickup & Return within 5 Miles of Downtown Chicago Center.
  • Driving Tour-Guide
Exclusions
  • Gratuities not included, but appreciated
  • Food is not included but tourist can be taken to any of the Chicago style Popcorn, Hotdog or Donuts.
Itinerary
  • Wrigley Field
  • Lincoln Park Zoo
  • Chicago History Museum
  • The Magnificent Mile
  • Michigan Avenue Bridge
  • Millennium Park
  • The Art Institute of Chicago
  • Chicago Cultural Center
  • Route 66
  • Grant Park
  • Museum Campus
  • Lake Michigan
  • Clarence F. Buckingham Fountain
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Infants are required to sit on an adult’s lap, Suitable for all physical fitness levels, A minimum of one person, and a maximum of 6 people, is required per booking., This is a small group tour/activity. Your group maybe combined with other small group., All travelers must be able to get in and out of the vehicle by themselves
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

2-Day Tour from Las Vegas | Grand Canyon South Rim & Lower Antelope Canyon & Monument Valley & Sedona

2-Day Tour from Las Vegas | Grand Canyon South Rim & Lower Antelope Canyon & Monument Valley & Sedona

5 (3 reviews)
KKday
$749
Book now
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2-Day Tour from Las Vegas | Grand Canyon South Rim & Lower Antelope Canyon & Monument Valley & Sedona
Summary

2-Day Tour departure from Las Vegas covering the Grand Canyon South Rim's endless spectacular views, the popular Horseshoe Bend with its precipitous cliffs, and Monument Valley. We will also take you to Lake Powell, Historic Route 66, and more!

Private Grand Canyon National Park South Rim Tour from Las Vegas

Private Grand Canyon National Park South Rim Tour from Las Vegas

12 hrsPrivate tourFree cancellationLikely to sell out
5 (4 reviews)
100%
0%
AmazingAmazing experienceexcellent guide
Viator
$1,595
Book now
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Private Grand Canyon National Park South Rim Tour from Las Vegas
Summary

Enjoy one of the Seven Wonders of the World with just your private group and your expert tour guide. You will see all the most scenic lookout points of this natural wonder. This is completely private tour to ensure the most personalized experience.

Inclusions
  • Bottled Water
  • Lunch
  • Expert Tour Guide
  • Entry to Grand Canyon National Park
  • National park entry fees (excludes additional non US resident government fees if applicable)
  • All Taxes and Fees
Exclusions
  • Gratuities
Itinerary
  • Mike O'Callaghan - Pat Tillman Memorial Bridge
  • Grand Canyon National Park
  • Grand Canyon Visitor Center South Rim
  • Mather Point
  • Yavapai Point
  • Route 66
Good to know
  • Infants and small children can ride in a pram or stroller, Not recommended for travelers with poor cardiovascular health, Suitable for all physical fitness levels, Please Note: National Park fees may apply for international visitors. If applicable, this fee is collected in-destination and not at the time of booking.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Grand Canyon Journey to the Bottom Tour on Historic Route 66|United States

Grand Canyon Journey to the Bottom Tour on Historic Route 66|United States

0
KKday
$299
Book now
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Grand Canyon Journey to the Bottom Tour on Historic Route 66|United States
Summary

Join us at the bottom of the Grand Canyon! Included in your tour is lunch and an extended drive on Historic Route 66 with a stop at the famous Route 66 Hackberry General Store.

Small Group Walking Tour of Chicago The Loop

Small Group Walking Tour of Chicago The Loop

2.5 hrsEco-FriendlyFree cancellation
0
Viator
$25
Book now
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Small Group Walking Tour of Chicago The Loop
Summary

Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through the heart of the city, you'll uncover fascinating stories, admire world-renowned architecture, and learn about the pivotal events that helpe...

Inclusions
  • Professional Spanish and English speaking local guide
Exclusions
  • Tips
Itinerary
  • The Rookery Building
  • Chicago Board Of Trade Building
  • Calder’s Flamingo
  • Route 66
  • The Art Institute of Chicago
  • Millennium Park
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

3 hrsPrivate tourEco-FriendlyFree cancellation
0
Viator
$7
Book now
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Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries
Summary

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower,...

Inclusions
  • Recommendations for the best photo opportunities
  • Immediate access to the audioguided circuit, no tickets or materials to collect
  • Offline mode (no data consumption during the visit)
  • 3 languages available: French, English, Spanish
  • 25 immersive audio comments along the way (History...)
  • Text transcripts of all audio content
  • Admire the hidden gems that lie off the beaten track
  • Interactive navigation with 3D map to discover the most beautiful streets,...
Exclusions
  • Entrance fees to paid establishments along the route...
  • Headphones or headphones (optional)
Itinerary
  • Chicago
  • The Chicago Theatre
  • Macy's on State Street
  • Cadillac Palace Theatre
  • Skydeck Chicago - Willis Tower
  • The Rookery Building
  • Calder’s Flamingo
  • Chicago
  • Route 66
  • Crown Fountain
  • Chicago Cultural Center
  • Jay Pritzker Pavilion
  • BP Pedestrian Bridge
  • Chicago
  • Chicago Fire Departament - Bomberos de Chicago
  • Chicago
Good to know
  • Service animals allowed, Public transportation options are available nearby, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Downtown Chicago Loop Walking Tour (Private)

Downtown Chicago Loop Walking Tour (Private)

2 hrsPrivate tourEco-FriendlyFree cancellation
0
Viator
$27
Book now
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Downtown Chicago Loop Walking Tour (Private)
Summary

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and se...

Inclusions
  • Visits to major landmarks including the Chicago Theatre, Millennium Park, Willis Tower, and more
  • Guided walking tour of the Chicago Loop led by a knowledgeable local guide
  • Insider stories about Chicago’s Great Fire, skyscraper innovations, and urban design evolution
  • Architecture and history commentary throughout the route
  • Opportunities for photos at Chicago’s most iconic sites
Itinerary
  • The Chicago Theatre
  • Marshall Field And Company Building
  • Skydeck Chicago - Willis Tower
  • Daley Center
  • Millenium Park
  • The Art Institute of Chicago
  • Route 66
  • Chase Tower
  • City of Chicago - City Hall
Good to know
  • Wheelchair accessible, Infants and small children can ride in a pram or stroller, Service animals allowed, Public transportation options are available nearby, Transportation options are wheelchair accessible, All areas and surfaces are wheelchair accessible, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Bike Adventure Tour in Beverly Hills, Santa Monica and Venice

Bike Adventure Tour in Beverly Hills, Santa Monica and Venice

5 hrsFree cancellation
0
Viator
$325
Book now
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Bike Adventure Tour in Beverly Hills, Santa Monica and Venice
Summary

This fun Los Angeles sightseeing bike tour offers you picturesque locations all over the city from the oceanside to the mountainous neighborhoods. Get to see the Hollywood Sign from the best points and take pictures of iconic instagrammable landmarks like Santa Monica Pier and Melrose Avenue. Ride ...

Inclusions
  • Must see and off the beaten path
  • Iconic places for photoshoot
  • 5-hour fun bike tour
  • Electric Bike and Standard Bikes available
  • Friendly Local Guide
  • Guided Walking Tour of Greystone Mansion grounds, gardens, Venice Canals, and Venice Boardwalk.
  • Free onsite storage for your bags
  • Expert tips and recommendations for more LA sightseeing
  • Helmet and safety vest
  • CPR/First Aid Certified Guide
Exclusions
  • Lunch
  • Gratuity
Itinerary
  • Third Street Promenade
  • Santa Monica Pier
  • Muscle Beach Venice Gym
  • Venice Beach
  • Melrose Avenue
  • 26-Mile Bike Path
  • Santa Monica State Beach
  • Pacific Design Center
  • Venice Beach Boardwalk
  • University of California
  • Sunset Boulevard
  • Santa Monica Bay
  • Two Rodeo Drive
  • Venice Canals Walkway
  • Route 66
  • Venice Skatepark
  • Brentwood Park
  • The Beverly Hills Hotel Spa
  • Paul Smith Los Angeles
  • Culver City
  • Malibu
  • Robertson Boulevard
  • The Abbey Food & Bar
  • Hollywood Sign
  • Marina del Rey Harbor
  • The Theme Building
  • Westfield Century City
  • Greystone Mansion and Park
  • Westwood
  • Abbot Kinney Boulevard
Good to know
  • Public transportation options are available nearby, Not recommended for travelers with spinal injuries, Not recommended for pregnant travelers, Not recommended for travelers with poor cardiovascular health, Travelers should have at least a moderate level of physical fitness, Please be ready for a few hills along this route, This LA tour covers 32 miles (51.5 km,) predominantly on bike paths, Closed-toe shoes are required, Young children (ages 6 and up) are welcome to join this bike tour, but they should be able to bike on their own, There will be a stop for lunch on Venice beach, halfway through this Los Angeles tour, We highly recommend our pedal-assist electric bike for all guests - it will still give you enough exercise. But for an extra challenge - you can go for standard bike, A moderate level of fitness is recommended
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Amarillo, Palo Duro Canyon and Route 66 Day Trip

Amarillo, Palo Duro Canyon and Route 66 Day Trip

6 hrsFree cancellation
3.71 (17 reviews)
73%
27%
AmazingFunexcellent knowledge
Viator
$779
Book now
View Details
Amarillo, Palo Duro Canyon and Route 66 Day Trip
Summary

We are the ONLY tour company in Amarillo! We want to make your trip memorable by providing everything you need for an unforgettable experience! This tour takes you on the most visited sights in Amarillo. We start with a tour of Downtown Polk St where you'll see the most historic buildings and learn ...

Itinerary
  • Amarillo
  • Palo Duro Canyon State Park
  • Canyon
  • Cadillac Ranch
  • Route 66 Historic District
Good to know
  • Suitable for all physical fitness levels, Recommended for ages 10 and up
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Pairs well with

Landmarks travelers visit on the same route as Historic Route 66.

Historic Downtown Flagstaff
Learn more

Historic Downtown Flagstaff

13 km away • from $29

Northern Arizona University
Learn more

Northern Arizona University

13 km away • from $129

Museum of Northern Arizona
Learn more

Museum of Northern Arizona

14 km away • from $18

Hot Springs National Park
Learn more

Hot Springs National Park

1682 km away • from $17

Frequently Asked Questions

Get answers to the most common questions travelers ask before visiting.

Across the booking platforms we compare, sightseeing tours make up the majority of options (57%), while walking tours account for the rest. Most tours are guided group experiences, though a small number are offered as private tours if you'd prefer a more personalized itinerary. Tours typically blend themes like nature, cultural history, and historical sites, so you'll get a mix of scenic drives, landmark stops, and storytelling about the road's iconic past.

Among the options we compare, prices typically range from $140 to $1,350, with most falling in the $322–$764 band and a median around $750. The variation reflects differences in tour length, what's included, and whether you're booking a group or private experience. Booking ahead is worth considering, since about 29% of the most popular options are flagged as likely to sell out.

Duration varies widely depending on the experience you choose. Tours typically range from about 2.5 to 10 hours, with most lasting around 4.5 hours. Shorter options work well if you're fitting Route 66 into a busy itinerary, while full-day tours let you explore more landmarks and scenery at a slower pace.

Most tours include a knowledgeable guide (57% of options), and some add drinks or entry tickets. About 57% of the options we compare offer free cancellation, and the same share provide instant confirmation, so you have flexibility when booking. Given that roughly 29% of tours are flagged as likely to sell out, booking ahead is a smart move if you have specific dates or a tour type in mind.

Tours are available in 8 languages: English, German, Spanish, French, Italian, Japanese, Chinese, and Korean. This breadth makes it easier to find a guided experience that suits your language preference, whether you're traveling solo or with a group.

Reviews are overwhelmingly positive, with an average rating of 4.78 stars across 154 combined reviews from the options we compare. Travelers consistently highlight guides as amazing, very knowledgeable, and helpful, and frequently use words like outstanding, fun, and excellent to describe their experience. The high review volume and consistently strong sentiment suggest these tours deliver on their promise.

Transportation varies by tour type. Among the options we compare, you'll find tours that travel by bus, car, or on foot, with each method equally represented across the listings. The choice depends on the specific tour and what aspects of Route 66 you want to experience—whether that's covering more ground by vehicle or exploring towns and landmarks on foot.

A small number of tours are tagged as eco-friendly across the platforms we compare, and about 14% of options are offered as private tours. If sustainability or a personalized, smaller-group experience matters to you, these are worth filtering for when you search, though they represent a smaller share of the overall selection.

Drive from Chicago to Santa Monica, covering 2,448 miles. Plan 10-14 days for the full journey, allowing time to explore iconic stops like the Grand Canyon and Cadillac Ranch.

Yes, many original segments are closed or replaced by I-40, I-44, and I-55. Use detailed maps or GPS apps designed for Route 66 to navigate remaining drivable historic sections.

Must-see stops include Cadillac Ranch in Texas, Petrified Forest in Arizona, Grand Canyon views, Seligman Barber Shop in Arizona, and Santa Monica Pier. Research regional favorites for your specific route segment.

Historic Downtown Flagstaff12.6kmNorthern Arizona University13.5kmMuseum of Northern Arizona13.7kmSunset Crater Volcano National Monument16.5kmSan Francisco Peaks20kmOak Creek Vista29.2kmCoconino National Forest34.6kmSlide Rock State Park37.8kmWupatki National Monument39.1kmOak Creek Canyon39.5kmSeven Canyons44.2kmDevil’s Bridge Trail44.9km