The Great American Roadtrip: Cruising Route 66 from Chicago to LA

Tour from Chicago to Los Angeles, USA

Your Travel Experience with ARRIVAL

Day 1

ARRIVAL

Land in Chicago and check in to your downtown hotel. Spend the afternoon visiting Millennium Park and snapping a photo with Cloud Gate (The Bean). Head to Willis Tower to test your nerve at the Skydeck glass ledge. Wrap up the evening with a stroll along Navy Pier or a deep-dish dinner.

Day 1 - 3

La Quinta by Wyndham Chicago Downtown

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.

Day 1 - 2

Millennium Park & Cloud Gate

Kick off your road trip at Chicago's most iconic sculpture, then stroll through the city's modern green space.

Skydeck Chicago, Willis Tower

Stand on a glass balcony 103 floors up. It’s a quick visit, but the photo opp is next level. Extra costs apply. 

Day 3 - 4

Pear Tree Inn St. Louis Near Union Station

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.

Day 3

Gateway Arch, St Louis

Ride a pod to the top of the tallest man-made monument in the U.S. for sweeping Mississippi views. Extra costs apply.

Day 4 - 5

Hampton Inn & Suites Springfield (Missouri)

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.

Day 5 - 6

Hampton Inn / SpringHill Suites Oklahoma City - Bricktown

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.

Day 6 - 7

Holiday Inn Express / Four Points by Sheraton Amarillo

Route 66-inspired comfort with easy freeway access. A convenient rest stop after Cadillac Ranch, featuring clean rooms, warm service and classic hotel amenities.

Day 6

Cadillac Ranch, Amarillo

Graffiti-covered Cadillacs half-buried in the Texas dust. This is everything an art installation should be. Spray cans encouraged (BYO).

Day 7 - 9

Best Western Plus Inn of Santa Fe

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.

Day 7 - 8

Santa Fe Old Town & Art Walk

A half-mile packed with galleries, local artists and Southwestern soul. Take your time strolling this one.

Day 9 - 10

Best Western / Fairfield Inn & Suites Gallup

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.

Day 9

Petroglyph National Monument

Stretch your legs on this cultural side jaunt. Hike short trails past 400–700-year-old carvings etched into volcanic rock.

Day 10 - 11

La Quinta / Hampton Inn Flagstaff

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.

Day 10

Petrified Forest & Painted Desert

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.

Day 11 - 12

Best Western Plus King’s Inn, Kingman

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.

Day 11

Grand Canyon Rim Walk

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.

Day 12 - 14

Excalibur Hotel and Casino, Las Vegas

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.

Day 12

Seligman Route 66 Stop

Pull over for pure Americana – Seligman’s neon diners, vintage motels and quirky mannequins make a living Route 66 time capsule.

Day 12 - 13

Las Vegas Strip

The Strip never sleeps. Hit the casinos, see a show, grab a cocktail and soak up the neon-fueled chaos only Vegas can deliver.

Day 14 - 15

Coast Anabelle Hotel, Burbank (Los Angeles)

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.

Santa Monica Pier

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.

Day 15

Departure

Spend your final day in Los Angeles at leisure. Visit Venice Beach, explore the arts district, or get some snaps by the Hollywood sign before heading home.