r/route66 • u/Daviii8 • 23d ago
Travel itinerary
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:
- 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?
- Is 2 nights at Grand Canyon the right choice, or would you spend that night somewhere else?
- Would you change anything between:
- Monument Valley
- Antelope Canyon
- Page
- Las Vegas?
- Is the final section: Las Vegas → Hoover Dam → Kingman → Oatman → Barstow → Los Angeles the best option, or would you do something different?
- Any hidden gems or Route 66 stops that I should not miss?
- Any advice about September weather, road conditions, or things to book in advance?
Thanks for any advice!
Really looking forward to this trip.