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The Great American Roadtrip: Cruising Route 66 from Chicago to LA
Hit the authentic Route 66 from Illinois’ Windy City all the way to the bright lights of Hollywood, past deserts, diners and plenty of dust-hued Americana
Overview
The lowdown
Iconic road trips on your bucket list? Say less. Welcome to a self-guided odyssey across the United States. This 15-night Route 66 road trip covers over 3,900 km of pop culture, geological marvels and fried roadside Americana. From Cloud Gate in Chicago to the Santa Monica Pier, the route rolls through eight states and a century of iconography. Expect deserts, diners, cowboy kitsch and city grit – with just enough chaos in Las Vegas to round things off. Playlists at the ready. You’re in for a rootin’ tootin’ time on this roadie.
Highlights
The best bits
Start of the Road: Cloud Gate & Chicago Skyline
Route 66 kicks off in downtown Chicago. Snap Cloud Gate, ride the Skydeck and get your bearings before hitting the road.
Itinerary
The day to day
Day 1
Arrive in Chicago, Illinois
Day 2
Explore Chicago
Day 3
Drive to St Louis, Missouri (480 km)
Day 4
St Louis to Springfield, Missouri (350 km)
Day 5
Springfield to Oklahoma City, Oklahoma (480 km)
Day 6
Oklahoma City to Amarillo, Texas (420 km)
Day 7
Amarillo to Santa Fe, New Mexico (450 km)
Day 8
Explore Santa Fe
Day 9
Santa Fe to Gallup, New Mexico (320 km)
Day 10
Gallup to Flagstaff, Arizona (300 km)
Day 11
Flagstaff to Kingman via Grand Canyon (250 km)
Day 12
Kingman to Las Vegas, Nevada (175 km)
Day 13
Explore Las Vegas
Day 14
Las Vegas to Los Angeles, California (450 km)
Day 15
Explore LA or Depart
Host
The experts
ARRIVAL
Curated by ARRIVAL, designed for you – adventure, comfort and local insight all in one.
Accommodation
The quarters
Modern, comfortable hotel in the heart of the Loop. Steps from Millennium Park, Willis Tower, and the riverwalk. Spacious rooms, gym access and free breakfast make it an easy city stay.
La Quinta by Wyndham Chicago Downtown
South Franklin Street, Ch...
Laid-back stop close to Union Station, downtown and the Gateway Arch. Cosy rooms, evening snacks and a hearty breakfast make it ideal for a relaxed overnight stay in the city.
Pear Tree Inn St. Louis Near Union Station
Market Street, St. Louis,...
Clean, bright rooms with all the Hampton touches. Close to historic downtown Springfield, Route 66 sites and local diners. Enjoy a pool, fitness center and complimentary breakfast.
Hampton Inn & Suites Springfield (Missouri)
North Glenstone Avenue, S...
Modern, well-equipped hotel in the heart of Bricktown. Easily walkable to buzzing restaurants, canal walks and bars. Stylish rooms, indoor pool and breakfast make it a fun OKC base.
Hampton Inn / SpringHill Suites Oklahoma City - Bricktown
East Sheridan Avenue, Okl...
Route 66-inspired comfort with easy freeway access. A convenient rest stop after Cadillac Ranch, featuring clean rooms, warm service and classic hotel amenities.
Holiday Inn Express / Four Points by Sheraton Amarillo
East Interstate 40 Highwa...
Southwestern adobe style meets modern comfort. Close to Santa Fe’s galleries, markets, and downtown plaza. Pool, hot tub and warm hospitality make for a restful two-night stay.
Best Western Plus Inn of Santa Fe
Cerrillos Road, Santa Fe,...
A comfy desert retreat surrounded by red-rock landscapes and Native American culture. Fresh rooms, friendly staff and easy highway access make it a great stopover.
Best Western / Fairfield Inn & Suites Gallup
East Historic Highway 66,...
A scenic base near the Grand Canyon and Route 66. Contemporary rooms, mountain air and easy access to trails, dining and Flagstaff’s historic downtown.
La Quinta / Hampton Inn Flagstaff
North Country Club Drive,...
Classic Route 66 vibes with retro-style interiors and all the modern comforts. Pool, free breakfast and a nostalgic roadside feel make it a fun, easy overnight.
Best Western Plus King’s Inn, Kingman
East Andy Devine Avenue,...
Whimsical castle-themed hotel right on the Strip. Bright, bold and buzzing with energy. Multiple pools, gaming floors and shows make it a full-Vegas experience.
Excalibur Hotel and Casino, Las Vegas
South Las Vegas Boulevard...
Boutique hotel with sleek, polished rooms and a relaxed atmosphere. Just minutes from major Hollywood studios. A calm, stylish end to a coast-to-coast adventure.
Coast Anabelle Hotel, Burbank (Los Angeles)
West Olive Avenue, Burban...
Activities
The fun stuff
Kick off your road trip at Chicago's most iconic sculpture, then stroll through the city's modern green space.
Millennium Park & Cloud Gate
Chicago, Cook County, US
Stand on a glass balcony 103 floors up. It’s a quick visit, but the photo opp is next level. Extra costs apply.
Skydeck Chicago, Willis Tower
Chicago, Cook County, US
Ride a pod to the top of the tallest man-made monument in the U.S. for sweeping Mississippi views. Extra costs apply.
Gateway Arch, St Louis
St. Louis, US
Graffiti-covered Cadillacs half-buried in the Texas dust. This is everything an art installation should be. Spray cans encouraged (BYO).
Cadillac Ranch, Amarillo
Interstate 40 Frontage Ro...
A half-mile packed with galleries, local artists and Southwestern soul. Take your time strolling this one.
Santa Fe Old Town & Art Walk
Santa Fe, Santa Fe County...
Stretch your legs on this cultural side jaunt. Hike short trails past 400–700-year-old carvings etched into volcanic rock.
Petroglyph National Monument
Western Trail Northwest,...
Stone trees and Mars-like terrain. There’s a small entry fee, but it’s well worth it for feeling like you’ve entered another planet.
Petrified Forest & Painted Desert
Petrified Forest National...
An absolute must-do activity – have you even completed Route 66 if you don’t take in the Grand Canyon?? Pay a small park entrance fee and then walk the paved Rim Trail for panoramic views and plenty of “whoa” moments.
Grand Canyon Rim Walk
Coconino County, US
Pull over for pure Americana – Seligman’s neon diners, vintage motels and quirky mannequins make a living Route 66 time capsule.
Seligman Route 66 Stop
Seligman, Yavapai County,...
The Strip never sleeps. Hit the casinos, see a show, grab a cocktail and soak up the neon-fueled chaos only Vegas can deliver.
Las Vegas Strip
Las Vegas, Clark County,...
Route 66 ends where the waves begin. Ride the Ferris wheel, play the arcades, snack on pier treats and soak up that west coast sun.
Santa Monica Pier
Los Angeles, Los Angeles...
Large SUV - 5 Seats Upgrade
Convertible - 2 Seats Upgrade
Fine Print
The small stuff
Cancel 65+ days out for a 70% refund. Within 64 days, we’ve locked in logistics, so no refund can be offered. Thanks for understanding – it keeps things running smooth for everyone.