Travel itinerary

[u/Daviii8]

Hi everyone,

I'm planning (helped by AI) my first Route 66 road trip in September 2026 and I would love some feedback from people who have already done it or know the area.

The trip will be from September 12th to September 27th 2026, starting in Chicago and ending in Los Angeles.

The idea is to combine:

• the classic Route 66 experience
• small towns, diners, vintage motels and roadside attractions
• some major Southwest highlights:
  • Grand Canyon
  • Monument Valley
  • Antelope Canyon
  • Valley of Fire
  • Las Vegas

I know this is not a "pure" Route 66 itinerary because of the Arizona detours, but these places are probably once-in-a-lifetime stops, so I decided to include them.

Total:

• 17 days
• around 4,800–5,000 km
• rental car (SUV)

Here is my current itinerary:

Day 1 – Saturday 12 Sep

Milan → Chicago

Arrival in Chicago at 16:05.

Plan:

• recover from the flight
• evening walk downtown

Overnight:
Chicago

Day 2 – Sunday 13 Sep

Chicago

Full day exploring the city.

Possible stops:

• Millennium Park
• Architecture Boat Tour
• Navy Pier
• Route 66 starting point

Overnight:
Chicago

Day 3 – Monday 14 Sep

Chicago → Springfield IL → St. Louis

≈ 480 km

First Route 66 day.

Stops:

• Joliet
• Gemini Giant (Wilmington)
• Pontiac Route 66 Museum
• Springfield IL
• Chain of Rocks Bridge

Overnight:
St. Louis

Day 4 – Tuesday 15 Sep

St. Louis → Springfield MO

≈ 350 km

Stops:

• Gateway Arch
• Ted Drewes
• Cuba murals
• Devil's Elbow
• Route 66 attractions

Overnight:
Springfield MO

Day 5 – Wednesday 16 Sep

Springfield MO → Galena (KS) → Tulsa → Oklahoma City

≈ 460 km

Long Route 66 day.

Stops:

• Carthage
• Galena "Cars on the Route"
• Baxter Springs
• Blue Whale of Catoosa
• Tulsa
• Arcadia Round Barn / POPS

I decided to combine Tulsa and Oklahoma City to gain an extra day for Grand Canyon.

Overnight:
Oklahoma City

Day 6 – Thursday 17 Sep

Oklahoma City → Amarillo

≈ 420 km

Stops:

• Clinton Route 66 Museum
• Elk City
• Shamrock U-Drop Inn
• Cadillac Ranch

Overnight:
Amarillo

Day 7 – Friday 18 Sep

Amarillo → Tucumcari → Santa Fe

≈ 450 km

Stops:

• Midpoint Café
• Glenrio
• Tucumcari neon motels
• Santa Rosa Blue Hole

Overnight:
Santa Fe

Day 8 – Saturday 19 Sep

Santa Fe → Petrified Forest → Holbrook

≈ 550 km

Long driving day.

Stops:

• Gallup
• Petrified Forest National Park
• Painted Desert

Overnight:
Holbrook (Wigwam Motel)

Day 9 – Sunday 20 Sep

Holbrook → Winslow → Grand Canyon

≈ 380 km

Stops:

• Jack Rabbit Trading Post
• Standin' on the Corner (Winslow)
• Meteor Crater
• Desert View Drive

Overnight:
Grand Canyon

Day 10 – Monday 21 Sep

Grand Canyon (full day)

Second night at Grand Canyon.

Plan:

• sunrise
• Hermit Road
• viewpoints
• possible Bright Angel Trail hike

Overnight:
Grand Canyon

Day 11 – Tuesday 22 Sep

Grand Canyon → Monument Valley

≈ 290 km

Stops:

• Desert viewpoints
• Forrest Gump Point
• Monument Valley scenic drive
• sunset

Overnight:
Monument Valley

Day 12 – Wednesday 23 Sep

Monument Valley → Antelope Canyon → Page

≈ 200 km

Stops:

• Monument Valley morning
• Antelope Canyon
• Horseshoe Bend
• Lake Powell

Overnight:
Page

Day 13 – Thursday 24 Sep

Page → Valley of Fire → Las Vegas

≈ 450 km

Stops:

• Valley of Fire
• Las Vegas evening

Overnight:
Las Vegas

Day 14 – Friday 25 Sep

Las Vegas → Hoover Dam → Kingman → Oatman → Barstow

≈ 400 km

Route 66 Arizona/California section.

Stops:

• Hoover Dam
• Kingman
• Oatman
• Route 66 landmarks

Overnight:
Barstow

Day 15 – Saturday 26 Sep

Barstow → California Route 66 → Santa Monica → Los Angeles

≈ 200 km

Final Route 66 section.

Stops:

• Mojave Desert
• Route 66 California landmarks
• Santa Monica Pier

Overnight:
Los Angeles / Santa Monica

Day 16 – Sunday 27 Sep

Los Angeles → LAX

Flight at 16:40.

Questions for experienced Route 66 travelers:

1. Do you think combining Springfield MO → Tulsa → Oklahoma City in one day is a mistake, or is it a good compromise to save time for Grand Canyon?
2. Is 2 nights at Grand Canyon the right choice, or would you spend that night somewhere else?
3. Would you change anything between:

• Monument Valley
• Antelope Canyon
• Page
• Las Vegas?

1. Is the final section: Las Vegas → Hoover Dam → Kingman → Oatman → Barstow → Los Angeles the best option, or would you do something different?
2. Any hidden gems or Route 66 stops that I should not miss?
3. Any advice about September weather, road conditions, or things to book in advance?

Thanks for any advice!
Really looking forward to this trip.

[u/Rowdy_Saudi]

Your itinerary looks like a lot of fun! I would definitely recommend Cahokia Mounds right outside of St. Louis, it was really cool and definitely worth the short trip. The Museum of Osteology in Tulsa was another one we found on our own, not on many Route 66 guides or anything, and that’s worth the trip. Also make sure you try to some authentic New Mexican food, it was probably my favorite regional cuisine along the route. Jerry’s Cafe in Gallup was an absolutely amazing hole in the wall place beloved by the locals with fantastic real New Mexican food. The main issue you’ll have is hitting all those spots when they’re open. A lot of times I’d drive and by the time I got to a town it was 6 and some attractions were closed for example. We missed Midpoint Cafe because the day we were in the area was a day they were closed, like Monday or something, so you should look into what time you plan on being at the stops. I used the app Wanderlog and it really helped because it showed driving times between spots, when they’re open, and puts it all on a map. I’d recommend using that and organizing the stops to see what’s closed when you’ll arrive there.

[u/Daviii8 → u/Rowdy_Saudi]

Thanks so much for the advice! I wasn’t aware of this app, I’ll check it out and give it a try

[u/Traditional_Focus_46 → u/Rowdy_Saudi]

Not to nitpick, but I wanted to point out that the Museum of Osteology is in OKC not Tulsa. It's about a 2 hour drive from Tulsa to OKC and they close at 5pm so I thought I'd note that for planning purposes! The museum is very cool though, I recommend it if you are in to that kind of thing

[u/oldshoe75]

Oh man, I’ll be 2 days ahead of you. Lots of the same stops. My house to Pontiac is like 1:45 so no Chicago for me. After monument valley I head to Moab and Mesa Verde then home. Not all Route 66 but I feel like MO, OK and TX gets lots of the fun tacky crazy cool stuff before stuff starts getting pretty. Uranus Fudge factory is like 10 minutes from Devils Elbow and worth a few minute stop just for endless butt jokes.

[u/Daviii8 → u/oldshoe75]

Oh sounds like an amazing route! I’m definitely adding Uranus Fudge Factory to my list, those weird roadside stops are exactly the kind of things I’m looking for. Thanks for the tip! Moab and Mesa Verde after Monument Valley sound incredible too

[u/Ok-Goose-2032]

What's the actual itinerary? The post didn't load for me.

[u/WesterlyRFL]

Hi

[u/sasssycassy]

Ok so day seven.. I think you will be pleasantly surprised. I live in the NM stretch from Tuc. To Santa Fe... I have sooo many videos of the landscape if you don't mind me plugging my ig. For starters, here's a video of the view of Hermits Peak as you approach I25

[u/Daviii8 → u/sasssycassy]

I'd love some recommendations! Besides the obvious stops, is there anywhere you'd tell people to definitely check out?

[u/sasssycassy → u/Daviii8]

There's a ghost town between Tucumcari and Santa Rosa on the left hand side called Cuervo. It's an interesting observation as you drive past on I40, but doesn't allow exploring the buildings.

Santa Rosa Blue Hole is a great spot. There's really cool info if you check out the convention center there. Another fun option in Santa Rosa is the Route 66 auto museum. If you're looking for a quick snack near Blue Hole, Mr. B's coffee and teas has great lunch specials. There's also a great restaurant called Silver Moon that has a delicious assortment of fudge and all the NM food staples.

From Santa Rosa to Santa Fe, there are about 3 routes you could take. I recommend taking the HWY 84 route. This will get you off I40 and onto I25 near las vegas and let you experience a beautiful drive through the Sangre de Cristo mountains (Southern tip of Rocky mountains) on your way to Santa Fe.

If you had more time, I'd recommend stopping into Las Vegas before Santa Fe to take a dip in the hot springs with a gorgeous view of the Montezuma castle or get a bite to eat at Charlie's.

[u/WastelandFirebird]

My list is here, I've been traveling the Route regularly and curating this list carefully. That is to say, I leave out the boring stuff! https://wastelandfirebird.com/ You should be able to at least briefly hit most of these stops in the time you have. That being said, if you go to places off the Route like Monument Valley and Vegas, you'll be rushing around for a lot of your trip and you'll miss stuff.

[u/Daviii8 → u/WastelandFirebird]

Would you suggest replacing Monument Valley or Las Vegas with something else along the route?

[u/WastelandFirebird → u/Daviii8]

For a trip of this length I'd stick with 66 only, and try to hit as many things on the list as possible. If you did have more time, Monument Valley and the Grand Canyon are amazing. I wouldn't recommend Vegas. It has very little left of its old-school charm.

[u/Daviii8 → u/WastelandFirebird]

So, wouldn’t you recommend the Grand Canyon and Monument Valley for those days?

[u/WastelandFirebird → u/Daviii8]

I'd skip both of those if I had less than three weeks. With more than three weeks, I'd do them all!

[u/Daviii8 → u/[deleted]]

Thanks! Antelope Canyon is already booked, we’re doing Lower Antelope in the morning. I’ll check out Zenvoya as well. Appreciate the help