2 weeks in United States for a group of friends
Embark on a legendary Route 66 road trip with friends, traversing from Chicago to Flagstaff over two unforgettable weeks. Begin in Chicago, savoring deep-dish pizza and exploring the Magnificent Mile. In St. Louis, ascend the iconic Gateway Arch and enjoy Forest Park's cultural treasures. Discover Oklahoma City's Western charm at the National Cowboy Museum and Bricktown district. Experience Amarillo's quirky Cadillac Ranch and Texan hospitality. In Albuquerque, ride the Sandia Peak Tramway for stunning views and explore Old Town's rich heritage. Conclude in Flagstaff, a gateway to natural wonders and stargazing at Lowell Observatory. This balanced journey blends cultural highlights with breathtaking landscapes.
Total Distance: ~3000 km
1 country • 12 nights
Your Stops:
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1st stop: CHICAGO
The starting point of Route 66, Chicago is a vibrant city with iconic architecture, deep-dish pizza, and lively neighborhoods.
Stay 3 nights
Explore the Magnificent Mile's Shopping Delights
Discover Millennium Park's Art and Architecture
Savor Authentic Chicago Deep-Dish Pizza

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3 nights, 1 adult
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Chicago River 90-Minute Architecture Tour

Chicago Architecture River Cruise

Chicago River 45-Minute Architecture Tour from Magnificent Mile
Chicago → St. Louis
Flight • 1.5 hours
$150.00 per person
2nd stop: ST. LOUIS
Known as the 'Gateway to the West,' St. Louis offers rich history, jazz music, and the iconic Gateway Arch.
Stay 2 nights
Ascend the Iconic Gateway Arch for Panoramic Views
Explore Forest Park's Museums and Gardens
Savor St. Louis Style BBQ at Pappy’s Smokehouse

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2 nights, 1 adult
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St. Louis → Oklahoma City
Flight • 1.5 hours
$180.00 per person
3rd stop: OKLAHOMA CITY
A key stop along Route 66, Oklahoma City blends Western charm with modern attractions like museums and entertainment districts.
Stay 2 nights
Visit the National Cowboy & Western Heritage Museum
Stroll Through Bricktown Entertainment District
Relax in Myriad Botanical Gardens' Urban Oasis

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2 nights, 1 adult
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Oklahoma City Indoor Skydiving with 2 Flights & Personalized Certificate

Art and Architecture Tour

Guided Streetcar Tour visit the Memorial, Downtown & Bricktown
Oklahoma City → Amarillo
Bus • 4.5 hours
$50.00 per person
4th stop: AMARILLO
Famous for its Cadillac Ranch art installation and classic Route 66 vibe, Amarillo offers unique roadside attractions and Texas hospitality.
Stay 1 night
Marvel at Cadillac Ranch's Quirky Art Installation
Experience Big Texan Steak Ranch's Legendary Meals
Explore Historic Route 66 District's Antique Shops

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1 night, 1 adult
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Amarillo, Palo Duro Canyon and Route 66 Day Trip

Amazing Amarillo Scavenger Hunt

Explore Amarillo with a Scavenger Hunt by Operation City Quest
Amarillo → Albuquerque
Bus • 4.5 hours
$60.00 per person
5th stop: ALBUQUERQUE
Nestled in New Mexico’s high desert, Albuquerque is known for its rich Native American heritage and vibrant arts scene.
Stay 2 nights
Ride Albuquerque's Sandia Peak Tramway for Stunning Views
Discover Old Town Albuquerque's Rich Cultural Heritage
Experience Balloon Fiesta Park's Hot Air Ballooning Thrills (Seasonal)

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2 nights, 1 adult
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Rio Grande River Valley Flight

Albuquerque Hot Air Balloon Rides at Sunrise

Albuquerque's Balloon Festival Aerogelic Ballooning
Albuquerque → Flagstaff
Train + bus • 7 hours
$70.00 per person
6th stop: FLAGSTAFF
Set against Arizona’s ponderosa pine forests near Grand Canyon National Park; Flagstaff serves as both an outdoor adventure hub & astronomical research center due dark skies ideal stargazing conditions! Perfect base camp exploring natural wonders nearby while enjoying cooler temperatures compared Phoenix/Tucson further south within state borders too! Known Lowell Observatory where Pluto discovered back 1930s historically significant site astronomers worldwide flock learn more about universe beyond our planet Earth itself…
Stay 2 nights

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2 nights, 1 adult
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Grand Canyon Railway Train Tickets

Antelope Canyon and Horseshoe Bend Day Tour from Flagstaff

Half-Day Private Grand Canyon Guided Hiking Tour
Flagstaff → Chicago
Flight • 3.5 hours
$250.00 per person