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Home » Trip Reports » Live And Let’s Drive: A Road Trip From LA To Chicago On Historic Route 66
Trip Reports

Live And Let’s Drive: A Road Trip From LA To Chicago On Historic Route 66

Matthew Klint Posted onJanuary 13, 2025January 13, 2025 33 Comments

Route 66 Road Trip

Welcome to my next trip report, which will be a bit unique…a Route 66 road trip across the United States instead of my usual airplane journey. We took a family vacation retracing the old Route 66 from Los Angeles to Chicago and had a smashingly good time.

Route 66 Road Trip: Across The Fruited Plain

I had to transport a car from LA to Chicago and rather than simply ship it, I thought it would be fun to show Heidi and the kids that there is more to the United States than Los Angeles or California. Heidi has lived in LA for a decade now but has never really gone beyond California outside of brief trips for funerals or work. It was time to change that.

Since we were traveling with Augustine, 8, and Claire Marie, 4, we took it rather easy. There were a couple of very long travel days, but it was a surprisingly refreshing journey. The easy pace allowed me to work each day as well. And mission accomplished: Heidi now has a much greater appreciation for the United States (an unfortunately for me, a greater desire–even before the fires–to leave Los Angeles).

I’m going to do this road trip day by day:

  • Day One: Relaxing In Scottsdale, Arizona 
  • Day Two: A Beautiful Journey To New Mexico Via Petrified Forest National Park
  • Day Three: A Tranquil Rest In Santa Ana Pueblo
  • Day Four: Historic Tucumcari Enroute To Oklahoma City
  • Day Five: A Cultural Awakening In Oklahoma City
  • Day Six: The Amazing Crystal Bridges Museum In Bentonville, Arkansas
  • Day Seven: The 12th Day Of Christmas At St Louis Arch

Then I will go back and highlight the hotels we stayed at in more detail:

  • Andaz Scottsdale
  • Hyatt Regency Tamaya Resort and Spa – New Mexico
  • Fordson Hotel Oklahoma City (Hyatt Unbound Collection)
  • Hyatt House Bentonville / Rogers, Arkansas
  • Hyatt Regency St. Louis
  • Hyatt Regency Deerfield, Illinois

Four hours to Chicago? How about seven days?! This trip was a lot more fun than I thought. After that, I have many lingering trip reports from 2024 that I hope to get done quickly…I want to keep trip reports moving in 2025.

Let me know if there is anything you’d like me to focus on as I share about this journey.

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About Author

Matthew Klint

Matthew is an avid traveler who calls Los Angeles home. Each year he travels more than 200,000 miles by air and has visited more than 135 countries. Working both in the aviation industry and as a travel consultant, Matthew has been featured in major media outlets around the world and uses his Live and Let's Fly blog to share the latest news in the airline industry, commentary on frequent flyer programs, and detailed reports of his worldwide travel.

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33 Comments

  1. Heather Reply
    January 13, 2025 at 2:42 pm

    My German relatives spent many summers visiting us and driving all over the country, often renting a motorhome when they didn’t borrow a car from my dad.

    I am very interested in hearing about Crystal Bridges.

    • Matthew Klint Reply
      January 13, 2025 at 4:19 pm

      Such a cool experience there. I could not believe I was in Arkansas and have a new level of respect for “Regnat Populus.”

  2. derek Reply
    January 13, 2025 at 3:02 pm

    In the film, Hunt for Red October starring Sean Connery, the second in command of the defecting Russian submarine wanted to buy a RV and travel around the country. It’s certainly different from NYC and LA.

    • Scott Reply
      January 13, 2025 at 3:28 pm

      “I would like to have seen Montana.”

  3. Santastico Reply
    January 13, 2025 at 3:08 pm

    Looking forward to the details of this trip.

    As for this comment: “an unfortunately for me, a greater desire–even before the fires–to leave Los Angeles)” Where would be the ideal location for you to move away from LA? I have done this exercise as we were planning our move once our kids were out of high school (I know the checklist will change as your kids get older) but curious to see your approach.

    • Matthew Klint Reply
      January 13, 2025 at 4:21 pm

      I’m a city slicker. I’ve lived in Los Angeles, Washington DC, and Philadelphia. I’m not sure I could live in the country…

      I could never sever ties with LA…maybe a for a period or even extended period, but my house will remain (as long as it doesn’t burn down…)

      • Santastico Reply
        January 13, 2025 at 5:15 pm

        I think you have to look at those experiences with a different set of eyes now. You probably lived in Philly and DC when you were not married and did not have kids. Now, kids become a huge part of your decision making process. And as you said, it could be that once they are in College, LA is the place for you to go back.

  4. Jerry Reply
    January 13, 2025 at 3:09 pm

    That sounds fun. I used to live in Bentonville (guess my employer), and that Hyatt House sucks! It used to be a Holiday Inn, and a pretty lousy one at that. I’m surprised you’re reviewing it.

    • Matthew Klint Reply
      January 13, 2025 at 3:58 pm

      You’ve lived all over!

  5. Oran Reply
    January 13, 2025 at 3:24 pm

    Great! This’ll be a change from your usual content! Also when will your Ethiopia trip report be coming out? What places did you visit in Ethiopia? When will the SAS, Virgin Atlantic & Air France reviews be out from your summer and autumn trips to Europe?

    • Matthew Klint Reply
      January 13, 2025 at 4:16 pm

      Here’s what I am thinking after this trip report:

      1. Royal Air Maroc, Morocco + Paris trip
      2. SAS A330, Brussels A330 Copenhagen trip
      3. Summer in Germany (United + Air France)
      4. Fall in Germany (Virgin Atlantic + JetBlue)
      5. Ethiopia (United + Ethiopian)

  6. Carter Kidd Reply
    January 13, 2025 at 3:25 pm

    You’ll drive through my hometown, Vinita, OK where the oldest family owned diner on rte 66 Clanton’s, Cafe, it has a huge neon EAT sign out front. Highly recommend! Safe travels!

    • Matthew Klint Reply
      January 13, 2025 at 4:31 pm

      Trip occurred – had I known, we would have stopped. Next time!

  7. marco Reply
    January 13, 2025 at 3:37 pm

    Andaz Scottsdale is nice but is 2 hour away from route 66, did you take a slight detour ?

    • Matthew Klint Reply
      January 13, 2025 at 4:31 pm

      We did take a couple detours.

  8. Andrew Y Reply
    January 13, 2025 at 3:39 pm

    Yay, Andaz Scottsdale! One of my favorite hotels

  9. Mike Reply
    January 13, 2025 at 3:52 pm

    Hope you got some fudge packed in Uranus

    • Matthew Klint Reply
      January 13, 2025 at 4:21 pm

      I thought that was a crude joke, but I see it is a Missouri attraction.

  10. John Ryan Reply
    January 13, 2025 at 3:56 pm

    Looking forward to hearing about the trip. What were your thoughts on the Deerfield Hyatt? The room was nice but the pools and nearby guests left a lot to be desired.

    • Matthew Klint Reply
      January 13, 2025 at 3:59 pm

      The top floor is remodeled…I like that. The gym and pool are okay. Breakfast is mediocre.

  11. DC Reply
    January 13, 2025 at 5:22 pm

    Oh boy- you should have asked for advice first! The Hyatt St Louis Regency is ….. less than perfect. Lots of more historic and interesting places to stay….

    At least you stopped in Bentonville. Shockingly interesting town.

    • Matthew Klint Reply
      January 13, 2025 at 6:04 pm

      I did speak to a close friend who is a road warrior. He recommended the Four Seasons in STL which would have been lovely, but we arrived at 2am…not worth paying 4x as much for what would have been a very short stay. And we had a great time at the Arch. Not a great hotel, though.

      He also recommended the 21c Museum Hotel in Bentonville, which would have been lovely, but we got in so late it just wan’t worthwhile.

      We did most of our travel in the evening.

  12. Mick Reply
    January 13, 2025 at 6:55 pm

    My wife and I did a road trip from San Fran to Jackson hole when we were first married. Really fantastic trip that ultimately encouraged us to move to Chicago for a few years with our 6 month old daughter. Ended up staying for 11 years! Great for the kids to experience living somewhat else.

    What’s the pull to live in Los Angeles? I couldn’t stand to live there with the traffic.

    • Matthew Klint Reply
      January 13, 2025 at 7:13 pm

      Family + church

      (it’s not the weather)

  13. MeanMeosh Reply
    January 13, 2025 at 7:57 pm

    Did you do this over Christmas? If so, we may have literally passed each other in opposite directions somewhere over New Mexico or Arizona.

    If I’d known you were planning this trip, I would have dared you to take the 72 ounce steak challenge at the Big Texan in Amarillo. I am curious, though. Why the big detour off 66 to go to Scottsdale?

    • Matthew Reply
      January 13, 2025 at 8:45 pm

      Yes, was during that period.

      And I saw all the 72 oz steak billboards!

      We went to Scottsdale because I wanted to review the Andaz there.

  14. Chi Hsuan Reply
    January 13, 2025 at 8:15 pm

    Awe getting out of your shithole of a city to see how the rest of flyover country lives? How enlightened of you.

  15. PM1 Reply
    January 14, 2025 at 12:17 am

    Looking forward to your road trip report! I’ve been thinking of taking something similar with my family.

    Also, how was Ethiopian? Thinking of flying them via a United award ticket.

    • Matthew Klint Reply
      January 14, 2025 at 8:53 am

      Ethiopian was excellent. I flew the A350 in business on the way down (LHR-ADD) and economy back (ADD-FRA) and enjoyed both flights.

  16. Bill Reply
    January 14, 2025 at 7:37 am

    Hello Matthew, Planning to take the trip this spring after shipping our car west from SC. Would be interested in how much of the original roadway you find, why you’re not stopping at historic hotels, and how many miles you travel daily- with time for kids and sightseeing. It looks like you will have a lot of seat time every day… billooltewah

    • Matthew Klint Reply
      January 14, 2025 at 8:18 am

      Hi Bill, we tracked old Route 66, but honestly we were not so strict about it. I’d say we just roughly followed it while trying to take the most direct path possible. You’ll see as the trip report unfolds.

    • MeanMeosh Reply
      January 14, 2025 at 10:36 pm

      As someone who’s driven about half of the original road so far, here’s my take.

      Most of the original road is drivable from Chicago to Adrian, Texas, a little west of Amarillo; from Moriarty NM (just east of Albuquerque) to just inside the Arizona border; from Ash Fork, AZ to Needles, CA; and from Amboy, CA to Santa Monica. Some of this does involve flipping between service roads on the interstates, backtracking where gaps occur, and navigating unmarked segments in both rural areas and big cities. Outside of these longer stretches, there are fragments you can access, though some are dirt roads I don’t recommend trying unless you have 4WD. The best preserved sections of old road are probably in Oklahoma. There’s even sections where you can drive the original 30s-era concrete pavement west of OKC.

      The whole route will probably take you twice as long as it would if you went straight through on the interstate. If you want to experience the “old school” 66 feel, you really need to skip the chains and stay in some of the kitschy cheap motels in the small towns, and check out the little diners and tourist trap-type attractions. You’ll also have to decide which of the many alternate alignments you want to stick to (the road was rerouted several times between 1926 and when it was decommissioned). If you’re contemplating this, I’d recommend either buying the hard copy EZ66 Guide for Travelers on Amazon, or the online guide at theroute-66.com.

      Happy driving if you end up doing it.

  17. Steven B Reply
    January 15, 2025 at 9:44 am

    That’s a good route. I’ve done about 3/4 of it.
    Tucumcari has such potential, I wish it got more attention and investment.
    Hope you liked the Fordson, it’s my goto in OKC.

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