My wife and I are planning a road trip on Route 66 in May of 2019. We live in South Florida and we are considering renting a car or SUV for the trip, starting in Miami and driving to either Chicago or Los Angeles and driving Route 66 one way between the two cities.
I have been doing a lot of research on the Web but I would like to get some input from those of you who have driven Route 66. One question...it seems like most people drive 66 from Chicago to Los Angeles rather than LA to Chicago. Is there a reason why?

Anyway thanks for your responses.

If you are going to rent a car, why not start in LA or Chicago and fly up there? Saves you a trip of 1.500miles

Sounds like fun! Be sure to hit up Cadillac Ranch outside of Amarillo and bring spray paint!

For the east-west factor, its probably the nostalgia for American westward expansion as well as going to the beach to cap off the trip.

dfwjim1 wrote:

. One question...it seems like most people drive 66 from Chicago to Los Angeles rather than LA to Chicago. Is there a reason why?

Historical context I think. "Making the trip out west on Route 66"

Perhaps because the more scenic parts are on the tail end as well. Gives a good goal to get to.

Good luck, I've only done the parts in missouri and Oklahoma, not really much there to see in a historical context really. A couple places tout the historical route 66 memorabilia stuff, but most of it is just replaced by highways 44 and 40 at this point. I'm sure with some more research, though, you'll be able to find good places to stop and enjoy.

I love road trips and have traveled the entirety of Route 66 on the interstate and much of the old road (note: the actual only original truly remaining stretch is between Kingman and Seligman, AZ, IIRC).

Anyhow, lot of touristy kitschy stuff, some interesting history, but it is surprisingly boring. I much prefer getting off the beaten path and there just isn't a lot to do in some very long stretches there.

If you want to do a road trip out west, get up to the mountains, crank through SW Colorado, hit the Durango-Silverton Railroad, or even better, the Cumbres-Toltec Railway. But rote driving just isn't a big appeal for me anymore. Do some digging. Also, Atlas Obscura is a good online reference!!

slider wrote:

I love road trips and have traveled the entirety of Route 66 on the interstate and much of the old road (note: the actual only original truly remaining stretch is between Kingman and Seligman, AZ, IIRC).

Anyhow, lot of touristy kitschy stuff, some interesting history, but it is surprisingly boring. I much prefer getting off the beaten path and there just isn't a lot to do in some very long stretches there.

If you want to do a road trip out west, get up to the mountains, crank through SW Colorado, hit the Durango-Silverton Railroad, or even better, the Cumbres-Toltec Railway. But rote driving just isn't a big appeal for me anymore. Do some digging. Also, Atlas Obscura is a good online reference!!

Vote #2 for this one. I've done the northern, middle and southern cross country routes and middle and south will melt your brain by the time you hit Kansas or Texas. Go north young man. I'd snake my way up through Georgia, TN and KY and then get up into Canada and hit the great lakes. On that run (done in a real no shit VW bus with bongs in the back) we came back down into MI and the Upper Peninsula before heading west into the Dakotas, Wyoming and Utah. If there is a god that would most certainly be his country and you could go just about any direction at that point and see some of the most amazing natural wonders in your lifetime. Canadian Rockies, national parks on either side, Colorado, Utah, NM, WA, OR, CA...I'm planning a two week road trip limited to just three of the inland western states and I already know it's not enough. Anyway, that's my advice. PS: also plan ahead to see if you can snag rooms in the Nat'l Park lodges. Some of them are well worth the expense (Yellowstone and Yosemite come to mind).

slider wrote:

I love road trips and have traveled the entirety of Route 66 on the interstate and much of the old road (note: the actual only original truly remaining stretch is between Kingman and Seligman, AZ, IIRC).

Anyhow, lot of touristy kitschy stuff, some interesting history, but it is surprisingly boring. I much prefer getting off the beaten path and there just isn't a lot to do in some very long stretches there.

If you want to do a road trip out west, get up to the mountains, crank through SW Colorado, hit the Durango-Silverton Railroad, or even better, the Cumbres-Toltec Railway. But rote driving just isn't a big appeal for me anymore. Do some digging. Also, Atlas Obscura is a good online reference!!

Vote #2 for this one. I've done the northern, middle and southern cross country routes and middle and south will melt your brain by the time you hit Kansas or Texas. Go north young man. I'd snake my way up through Georgia, TN and KY and then get up into Canada and hit the great lakes. On that run (done in a real no shit VW bus with bongs in the back) we came back down into MI and the Upper Peninsula before heading west into the Dakotas, Wyoming and Utah. If there is a god that would most certainly be his country and you could go just about any direction at that point and see some of the most amazing natural wonders in your lifetime. Canadian Rockies, national parks on either side, Colorado, Utah, NM, WA, OR, CA...I'm planning a two week road trip limited to just three of the inland western states and I already know it's not enough. Anyway, that's my advice. PS: also plan ahead to see if you can snag rooms in the Nat'l Park lodges. Some of them are well worth the expense (Yellowstone and Yosemite come to mind).

slider wrote:

I love road trips and have traveled the entirety of Route 66 on the interstate and much of the old road (note: the actual only original truly remaining stretch is between Kingman and Seligman, AZ, IIRC).

Anyhow, lot of touristy kitschy stuff, some interesting history, but it is surprisingly boring. I much prefer getting off the beaten path and there just isn't a lot to do in some very long stretches there.

If you want to do a road trip out west, get up to the mountains, crank through SW Colorado, hit the Durango-Silverton Railroad, or even better, the Cumbres-Toltec Railway. But rote driving just isn't a big appeal for me anymore. Do some digging. Also, Atlas Obscura is a good online reference!!

I'm going to add a 3rd vote for this.

Most of the historic Rte 66 stuff is getting harder and harder to find. The history of the road is interesting but you have to remember that pretty much after WW2 various states began upgrading the highway that the original route ran on. With the exception of the business loops through random towns, much of the alignment of I 55, 44 and 40 is more or less the same as the old road. And a lot of the older alignments are abandoned or just gone.

Here in ABQ Central Ave is the old Rte 66 and while there are some gems left over and some have been well rehabed and re purposed, the rest of the route is frankly kind of depressing. That's true for a lot of the towns from Oklahoma to Arizona, just on a smaller scale.

We drive Route 66 a couple of years ago from Los Angeles to Flagstaff. meh. Maybe it is just me. We stayed in Williams, AZ. It plays up the nostalgia of Route 66 very well. There are parts of the old road in the desert near Barstow. On a different trip, we saw the western terminus marker for Route 66 on Santa Monica Pier. We also saw some passenger jets in storage in Kingman. It is not so much the scenery but the towns along the way.

Dutchy wrote:

If you are going to rent a car, why not start in LA or Chicago and fly up there? Saves you a trip of 1.500miles

Forgot to mention that we are planning to visit Nashville, Dallas and Las Vegas along the so we will be making some side trips.

If you're committed to the southerly route just know that it's flat, dry and very monotonous. I highly recommend bongs (and/or mescalin) if you're so inclined. If not at least bring a copy of Fear and Loathing in Las Vegas to prepare you for the Strip. Of course it's all different now..sniff sniff.

wingman wrote:

If you're committed to the southerly route just know that it's flat, dry and very monotonous. I highly recommend bongs (and/or mescalin) if you're so inclined. If not at least bring a copy of Fear and Loathing in Las Vegas to prepare you for the Strip. Of course it's all different now..sniff sniff.

PS: by sniff sniff I mean so sad..so sad.

dfwjim1 wrote:

Dutchy wrote:

If you are going to rent a car, why not start in LA or Chicago and fly up there? Saves you a trip of 1.500miles

Forgot to mention that we are planning to visit Nashville, Dallas and Las Vegas along the so we will be making some side trips.

So how much time do you have for this trip? And how much driving do you really want to do? Also, since you're heading out in late May, you should have decent weather if you're going anywhere into the mountains.

I hit the Black Hills last year for the first time and utterly loved the place. The San Juans in CO are an amazing drive, and many parts of UT. Yellowstone, Arches, Badlands, all of it...it's pretty incredible to get out and visit those places.

Unfortunately, if BNA-DFW-LAS are nodes in your journey, that makes trip planning interesting. MEM has some great history if you're a music lover, and obviously BNA is self-apparent in that regard.

trpmb6 wrote:

Historical context I think. "Making the trip out west on Route 66"

Perhaps because the more scenic parts are on the tail end as well. Gives a good goal to get to.

Very true, however for that reason it saves you a few bucks if you drive it the other way.

I've once been told that car rental companies see a lot of their Chicago-based rental cars (with Illinois license plates) being returned in Los Angeles. These cars need to be brought back to Chicago, but due to the fact that more people drive Chicago - Los Angeles than Los Angeles - Chicago they keep getting a surplus of Chicago-based cars.

Therefor, if you rent a car in Los Angeles and you tell them you're driving Route 66 to Chicago they practically give you the car for free. Good chance it has Illinois license plates on it, somebody else just drove Route 66 in the other direction with it. In Chicago you pay a lot more for a rental car for driving the same route because after you've finished they need to get the car back to Chicago.

Furthermore, as has already been said, Miami is not a good starting point for driving Route 66. Instead of driving from Miami to Los Angeles or Chicago, it's better to fly this part of the journey.

Thanks folks for all of the information. My wife and I are planning to take 2 weeks so flying to Los Angeles and renting a car eastbound seems like the best option. Seems like the best trip would be to take a northern route going through Las Vegas and then up to Yellowstone and a northern route. I have been to OKC, TUL and ABQ a few times so seeing those cities is not a big deal.

The roads have been renumbered several times. Beware of what is now called 66. There is way more Americana and history on the original route no longer numbered as 66. There are websites about the original brick paved roads. Some still in existence. For genuine history, choose a good small town like Ft Madison in Iowa or many such others and spend a few days with a local guide to truly immerse yourself in the vibe, which can hardly be done if you do not interact in depth with the natives. Otherwise you could just watch a travel video.