Motorcycling in Route 66, Chicago – Los Angeles, Illinois USA

Trail length:
2400 mi/3862 km
Ride duration:
15 days
States that the trail is passing through:
Best season:
Spring, summer, fall
Average temperature:
55 - 105°F / 13 - 41°C
Chicago is the seat of Cook County, Illinois, USA. It is the third most populous city in the US and the most populous city in both the American Midwest and Illinois. Nicknamed as The Second City or Windy City, Chicago is situated on the southeastern shores of Lake Michigan, in the northeastern Illinois.

Known as the Mother Street of America or Main Street of America, Route 66 is a famous motorcycling tour that travels through the original Route 66, promising many, genuine, motorcycling experiences over amazing picturesque landmarks, roads, scenery and places.

It is a 2400 mi/3862 km long road that starts from Chicago, Illinois and after passing through 8 states and 3 different time zones, it ends up to Los Angeles.

Illinois, Missouri, Kansas, the city of Oklahoma, Texas, the city of New Mexico, Arizona and California are the states that Route 66 is passing through, being the path of desperadoes, dreamers, migrants and an entire vacationers generation wanting to discover the way west.

Route 66’s glory days were the 1950’s, when cars and motorcycles rode bumper to bumper, in order to experience the Western frontier. Restaurants, hotels, motels, gas stations are spread up everywhere. Most of the nostalgic landmarks are still preserved, as they were in the 1950’s.

For 15 days, you will follow the steps of many motorcyclists that rode this awesome trail before. You will start at Chicago and continue on the second day for the first 187 mi/301 km to Springfield. On the third day, you will ride 116 mi/187 km of amazing trails and sightseeing until Saint Louis, MO.

Day four continues with the next 335 mi/539 km to Joplin, MO, where you can enjoy the nice hospitality of Missouri. Next 255 mi/411 km are on day five to Oklahoma City, OK, which is the heart and soul of Route 66 country. Day six and you will enter Texas and Amarillo city at the next 266 mi/428 km.

On day seven, you will leave Texas with a bittersweet feeling, as the Texan experience cannot be easily forgotten and continue to New Mexico, at the city of Santa Fe for the next 303 mi/488 km. It is recommended to spend day eight as a leisure day in the city of Santa Fe. Next city is Gallup again in New Mexico and 200 mi/322 km away.

On day ten, Grand Canyon Arizona is your next destination. After 283/456 exciting mi/km, you will be standing in front of this miracle created by mother nature. Make sure to take a lot of photographs to capture the moment. On day 11, you will leave Grand Canyon and enter Nevada and the city of Laughlin, 256 mi/412 km away.

Next stop on day 12 and after 129 mi/208 km Las Vegas! Make sure that you will remember exiting the most lighted town in the world, as you can see it from outer space and visit a casino, where time stops!! Many famous hotels and actor mimics are waiting for you to discover them.

If you manage to leave this city – magnet, you will find yourself after 282 mi/454 km entering California and the city of Victorville. There the legendary Route 66 contains the Devil’s Playground and a ride along the Mojave Desert that offers the most dramatic scenery of the Southern California.

Days 14 and 15 are when the trip is over, as you enter and cross the city of Los Angeles after 124 mi/200 km. When passing the sign marking the end of the trail, you will feel like the next ride is only a dream away. Are you ready to live it again??

How to Get to Destination

BY CAR FROM Springfield
202 miles/325 km, 3 hours 7 minutes
Head east toward S 9th St. Turn left onto S 9th St. Turn right onto E Madison St. Continue onto IL-97 W/E Clear Lake Ave. Take the exit onto I-55 N toward Chicago. Take the U.S. 41 N/Lake Shore Drive N exit on the left. Merge onto U.S. 41 N/S Lake Shore Dr. Turn left onto E Jackson Dr.
BY CAR FROM Lawrenceville
262 miles/421.6 km, 4 hours 23 minutes
Head west on State St toward 11th St. Turn right onto IL-1 N/15th St. Continue to follow IL-1 N. Turn left onto IL-133 W/W Jasper St. Continue to follow IL-133 W. Turn right to merge onto I-57 N. Merge onto Interstate 94 W. Keep left to continue on Interstate 94 Express W. Take exit 53C toward Interstate 55 N/Stevenson Expressway/Lake Shore Drive/22nd Street. Keep right at the fork, follow signs for I-55 N/Stevenson Expy/Lake Shore Dr and merge onto I-55 N/Stevenson Expy. Take the U.S. 41 N/Lake Shore Drive N exit on the left. Merge onto U.S. 41 N/S Lake Shore Dr. Turn left onto E Jackson Dr.
Chicago O'Hare International Airport,
19.2 miles/31 km

If you wish to travel by train, Amtrak has stations almost at the entire Illinois. Take a train from anywhere in the US or Illinois and abort in Chicago – Union Station, IL (CHI). From there you can use the public transportation or rent a car.


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