My Route 66 Road Trip from Chicago to LA: How Many Days, the Best Itinerary, My Favorite Stops, Where to Stay, Etc.

This post is part of a series I’ve done on Route 66. In 2022, I drove the entirety of Route 66 from Chicago to Los Angeles. 2500 miles, 8 states, countless stories, and an endless stretch of small towns, neon, diners, motels, and roadside attractions. Read through all of my Route 66 posts here. They’re also linked at the end of this post. If you’re planning your own Route 66 road trip, either the whole thing or just a part, I hope these help you out. Enjoy the drive!

Well, I DID IT!! I’m writing this post in October 2022 and I’ve finally finished my Route 66 road trip. 

At the beginning of the year I made a pretty bold statement to my friends and family…”I am going to drive the entire length of Route 66 this year!” I got a few “wow that’s cool” responses, a bunch of glazed over stares, and even a flat out “there’s no way you’ll do the whole thing this year-that’s over 2000 miles!”

Well, it’s over 2500 miles to be precise and it took a LOT of planning, some willing travel buddies, and a lot of miles on my Toyota 4Runner, but I finally did it. 

Yes, I know most people do Route 66 as one big road trip, but since I was committed to covering it for the blog (aka stopping and seeing every little thing) and I didn’t want to carve out the roughly 4-6 weeks that would’ve probably taken me, I decided to split it up into sections throughout the year. 

Now, there are a billion Route 66 resources on the Internet, many by people who have a lot more experience and history with the road than I do. So I’m not attempting to put together the “ulimate guide” for driving Route 66 here. But I always find first hand info and advice super helpful when I’m planning my trips, so I’m going to let you know how I did it and how I would do it if I did it again. Because you can’t know what you don’t know, right?

I’ll put my disclaimer here…I’m probably not your average Route 66 traveler. I’m all for the adventure of the road, I love a good neon sign, and I’m very drawn to the vintage Americana vibes that the route is famous for. But I also like to stay in “nicer” hotels, I get bored eating diner food after a few days, and I like a PLAN. 

So the whole making no reservations and seeing whatever “vintage” motel might have a room for you when you roll into town that night just isn’t my style. 

That being said, here was my approach to driving Route 66:

I decided it was MY trip and I didn’t have to do it the way Bob from Wichita, Kansas in one of the big Route 66 Facebook groups said I’m “supposed to.” 

And I think that goes for YOU too. You’re allowed to do it the way you want to. You don’t have to follow somebody else’s rules for what “counts” and how it should be done. You can hop on and off the interstate. Stay in nicer hotels, deviate for side trips, etc. 

I personally live on Route 66 in Tulsa, OK, and I’ve spent a good part of my life traveling on the interstate along Route 66 and going to cities and towns that it passes through. So for some of the states that are more familiar to me (Oklahoma, Kansas, Missouri, Texas), I was focused more on Route 66 itself and didn’t deviate much from it. Honestly, in this stretch I rarely went more than a couple blocks off of the official route. I wasn’t interested in scoping out what else there was to do in St. Louis, Springfield, Tulsa, OKC, Amarillo, etc. because I’ve been to those places before or I figured they’re close enough to where I live that I can visit another time.  

But for the rest of the states (some of which I’d never been to at all), I approached it as wanting to see what the state had to offer. What is it famous for? What can you see and do there that you can’t do anywhere else in the world?

Basically, I think if you’re from the US and you’ve done extensive traveling through the middle of the country, you may choose to be more hyper focused on just staying on the route and hitting all the little Route 66 spots. But I f you’re not from the US (or you’re from a coast), I think it’s a great opportunity to really “see America” and I’d focus on the route more loosely and give yourself time to have the best experiences along the way. Go to a baseball game in Chicago! Hang out in a jazz or blues club in St. Louis! Visit an Indian reservation in Oklahoma! Attend a rodeo in Texas! Go to the Grand Canyon! Etc. etc. 

Also, I mentioned before…I like nicer places to stay. It doesn’t have to be the Four Seasons, but if we’re talking the spectrum from Motel 6 to Ritz Carlton, I’d say a Courtyard Marriott is about as low as I like to go. 

And where I stay really makes or breaks a trip for me. So I spent a LOT of time and based most of my itinerary around where I would stay. I knew I wanted to do some vintage Route 66 motels and keep the chains to a minimum. But I also wanted to throw in some nicer historic boutique hotels along the way to break it up.

My Route 66 Road Trip

I was born and raised in Tulsa, OK with the Mother Road practically in my backyard, but it wasn’t until a certain Pixar movie came out that I took a little more interest. 

Tulsa has done a lot to preserve and play up our spot on the route in the last decade or so, but I’d never even considered Route 66 outside of our area. 

But I’ve always been drawn to kitschy roadside attractions and classic Americana so when COVID had me locked down from traveling too far, I decided a couple of day trips to see all of Route 66 in Oklahoma would be a fun diversion. 

Well I’m a project person at heart and I love a far fetched but achievable goal so after I started doing the research, I decided to drive the entire route. 

Besides personal intrigue, my big mission for traveling the entirety of Route 66 is to help other people who want to take this trip. So most of my content on my blog is geared towards travelers who are driving the entire road continuously or are at least doing a large chunk of the road on one trip. 

So based on my personal experience, here’s my best advice about driving Route 66:

My Favorite Stops & Moments

I’ve done pretty extensive trip reports/write ups from point to point along Route 66 that include so many places and stops, but now that I’ve done the whole things, looking back…these were my absolute favorite stops along Route 66:

Beginning of the Route in Chicago, IL

Pontiac Oakley Auto Museum in Pontiac, IL

Illinois Route 66 Hall of Fame in Pontiac, IL

World’s Largest Covered Wagon in Lincoln, IL

Gateway Arch in St. Louis, MO

The Candy Crown Kitchen in St. Louis, MO

Ted Drewes in St. Louis, MO

Wagon Wheel Motel in Cuba, MO

Route 66 Car Museum in Springfield, MO

Gary’s Gay Parita in Halltown, MO

Old Riverton Store in Riverton, KS

Dairy King in Commerce, OK

Totem Pole Park in Foyil, OK

Blue Whale in Catoosa, OK

Buck Atom’s in Tulsa, OK

Rock Cafe in Stroud, OK

Oklahoma Route 66 Museum in Clinton, OK

National Route 66 Museum in Elk City, OK

U Drop Inn & Cafe in Shamrock, TX

6th Street Antique Shops in Amarillo, TX

Cadillac Ranch in Amarillo, TX

Midpoint in Adrian, TX

Blue Swallow and Teepee Curios in Tucumcari, NM

The Dog House in Albuquerque, NM

El Rancho Motel in Gallup, NM

Petrified Forest National Park & Painted Desert, AZ

La Posada in Winslow, AZ

Downtown Flagstaff

Turquoise Teepee in Williams, AZ

Burma Shave Signs in Seligman, AZ

Snow Cap in Seligman, AZ

Hackberry General Store in Hackberry, AZ

Drive Through Sign at the Arizona Route 66 Museum in Kingman, AZ

Oatman Highway, AZ

La Casa de Desierto Harvey House in Barstow, CA

Santa Monica Pier, CA

How Many Days to Drive Route 66?

Well, how many do you have? ; ) You could spend months traveling the route and not be able to see and do everything. 

And while I’m firmly in the camp of do whatever works for you and sounds like fun (a three week road trip isn’t everybody’s idea of a good time)…here are my general thoughts…

Two weeks is probably the minimum amount of time I would carve out if you’re going to do the full route. 

You could do it in 10 days if you’re really clear about exactly what you want to see and do along the way and you stick to a good plan. Plus if you’ve already been through some of the towns and cities along the route. 

But three weeks is probably the sweet spot. In three weeks you should be able to stop in most place so interest and maybe even do a few side trips. 

The Best Three Week Itinerary

Day 1: Arrive in Chicago

Day 2: Chicago

Day 3: Chicago to Springfield, IL

Day 4: Springfield, IL to St. Louis

Day 5: St. Louis to Cuba

Day 6: Cuba to Springfield, MO

Day 7: Springfield, MO to Tulsa

Day 8: Tulsa to OKC

Day 9: OKC to Amarillo

Day 10: Amarillo to Tucumcari

Day 11: Tucumcari to Albuquerque

Day 12: Albuquerque to Santa Fe

Day 13: Santa Fe/Taos

Day 14: Santa Fe to Gallup

Day 15: Gallup to Winslow

Day 16: Winslow to Flagstaff

Day 17: Grand Canyon

Day 18: Flagstaff to Kingman

Day 19: Kingman to San Bernardino

Day 20: San Bernardino to Santa Monica

Day 21: Santa Monica to…

In the next section, I’ve got recommendations for places to stay that coincide with most of these overnights. 

Where to Stay on Route 66

I’ve done an entire post about where to stay on Route 66 here. It’s extensive

But to sum it up…if you’re only going to stay in one historic Route 66 motel, make it the Blue Swallow in Tucumcari, NM. If you’re going to make it two, hit up the Wagon Wheel in Cuba, MO. And if you’re going to make it three, you’ve got to stay in a Wigwam (but make it the one in San Bernardino, CA not the one in Holbrook, AZ). 

El Vado in Albuquerque, El Rey Court in Santa Fe, and the High Country Motor Lodge in Flagstaff are all FABULOUS historic Route 66 motor courts that have been 100% renovated in a very modern and comfortable way. I can’t recommend them enough. 

El Rancho Motel in Gallup, NM and La Posada in Winslow, AZ are beautiful historic properties that have been kept up in a really nice way and are worth a stay. I wouldn’t put them in the “vintage motel” category, but they’re not quite entirely modern either. 

Chicago, St. Louis, Springfield MO, Tulsa, OKC, and Amarillo all have GREAT historic (but high end) boutique hotels to make the trip a little more plush. 

Chicago: The Blackstone

St. Louis: Hotel St. Louis & The Chase

Springfield, MO: Hotel Vandivort

Tulsa: The Mayo & Tulsa Club Hotel

OKC: The National & The Skirvin

Amarillo: The Barfield 

All of the options I’ve mentioned above give you pretty solid coverage for places to stay along the route, but I found a few “holes” where I ended up going with a chain because options were lacking. 

Surprisingly, Springfield, IL doesn’t have a ton of great hotel options (surprising because all of the Abraham Lincoln sites draw a crowd) and you’re definitely going to want to spend the night so I went with a Courtyard Marriott. It was a little rundown looking on the outside, but the rooms were great. 

I also ended up at a SpringHill Suites in Kingman, AZ. Kingman (on the western border of Arizona) feels a bit like the final outpost on the frontier). Once you leave Kingman, it’s a long lonely stretch through the brutal Mohave desert before you come into LA’s city sprawl. And there just weren’t a ton of places I was interested in staying between Kingman and LA. 

Once you get to LA, the options are endless. Most people probably want to stay in Santa Monica to visit the pier, but honestly if you’ve never been to California before, I’d hate for that to be your final impression of the state. Beverly Hills and Hollywood are something to see (and both have plenty of posh hotels). 

I stayed a couple of nights at the Hotel June in West LA just for an inexpensive location to do a few city things. It was fine, I honestly wouldn’t really recommend or not recommend it. 

But I would recommend making your final destination in California somewhere else. Head on down to Disneyland, drive the Pacific Coast Highway down through Huntington Beach and Laguna or up through Malibu and Santa Barbara. There is sooooo much to see and do in California. 

Is Route 66 Worth Driving?

I’ve gotten a lot of mixed reactions when telling people about my Route 66 road trip. Most people are impressed by the scope and commitment or know that it’s something special. But I’ve had several people ask me what’s the big deal? Funnily enough, that reaction usually comes from people who live on or around Route 66. 

Because of Route 66’s centennial in 2026, it’s starting to be a “big deal” in a lot of towns and cities like Tulsa who are ramping up construction on big projects to roll out in time to welcome the extra burst of travelers. So we’re hearing a lot about it, and for a lot of people who grew up with this in their backyards, it can be a little baffling that people come from all over the world to drive this road. 

But honestly, there’s never been a better time to drive Route 66! Cities and towns across America are gearing up for the centennial celebration by opening up new businesses, spiffing up more rundown parts of town, putting together festivals and passport stamp locations and fun things to do along the route. 

Here’s the deal…if you’re the type that likes to spend your vacations at an all inclusive in Mexico, I’m not going to try to convince you to drive Route 66. But if you’re already inclined to, I definitely think it’s worth doing. 

Would I Drive Route 66 Again? 

While I may end up revisiting certain places along Route 66 in the future, the trip was definitely a one and done for me. 

Driving Route 66 was a big personal bucket list trip/project for me and I’m 100% glad that I did it, but I’ll be honest…I think I liked it more in theory than in reality. 

I have great memories and saw so many cool things on the trip, but I think it just didn’t totally jive with my travel style. I’m definitely more of a destination traveler. I like to settle into a place and really get to explore (and relax), and on a big trip like this, I felt like I always had to keep going, keep pushing, go just a little further. 

What I loved most about driving Route 66 was the “seeing America” part. Watching the landscape and cultures change from Illinois, Missouri and Kansas through Oklahoma and Texas and onto New Mexico, Arizona, and finally, California is (for me at least) the best part of the trip. 

And I’ll definitely keep focusing most of my travel on seeing parts of the country that I haven’t been to yet.

Planning a Route 66 road trip? I’ve got all of the info you need! 

I’ve written about my cross country road trip pretty extensively section by section. Read them all here: Part 1 (Chicago), Part 2 (Chicago to St. Louis), Part 3 (St. Louis), Part 4 (St. Louis to Springfield MO), Part 5 (Springfield, MO), Part 6 (Springfield, MO to Tulsa), Part 7 (Tulsa), Part 8 (Tulsa to OKC), Part 9 (OKC), Part 10 (OKC to Amarillo), Part 11 (Amarillo), Part 12 (Amarillo to Albuquerque), Part 13 (Albuquerque), Part 14 (Albuquerque to Flagstaff), Part 15 (Flagstaff), Part 16 (Flagstaff to San Bernardino), Part 17 (Los Angeles). 

Plus I’ve done roundups by state: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California.

I’ve got the scoop on where to stay including the best Route 66 motels recommendations

And finally, my final trip recap where I spill the beans on how many days you need, the best itinerary, my favorite don’t miss spots, and other tips.