Route 66: the Day-by-Day Itinerary
Route 66 is the great American road trip, done properly. It starts with Chicago blues and St. Louis' arch, rolls through neon motels and Texas steakhouses, detours to the Grand Canyon, and ends where the road runs out at the Santa Monica pier. The point isn't the destination — it's everything along the way.
Route 66 is a 3940 km one-way journey (self-drive). It works best as 8–13 days; the plan below is the 10-day version for May, built from 806 verified places, with real road-routed transit times, opening hours and daylight checked.
Customize this plan → 8-day plan · 10-day plan · 13-day plan · best time to go
10
days
3811 km
distance
44.8 h
driving
54
curated stops
💡 Good to know for this plan
- Heavy transit: day 1 (6h10), day 3 (7h53), day 8 (6h05), day 10 (10h12) run over 6 hours on the road. Around 11 days would keep daily driving comfortable on this route — or keep the dates and start each of those days by 08:00.
Day 1 Chicago → St. Louis
🌡 1.1–33.3°C · 🌧 ~19 rain days · ☀ 14.1h light
09:00
Chicago Water Works Visitor Information Centermuseums & heritagehistory & sagascoffee & bakes
Discover historic architecture and free visitor materials in the Pumping Station.
50 min · Chicago
open: Jan 2-Mar 15: Sa Su 10AM-5PM; Mar 16-May 26: Su 10AM-5PM, M-Sa 9:30AM-
09:50
Chicago Loop Synagoguelocal & traditional
Witness traditional Jewish rituals in the heart of the city.
50 min · Chicago
10:40
Downtown Islamic Centermuseums & heritage
Join the peaceful Friday prayers and community spirit here.
50 min · Chicago
18:30
Das Bevocraft beer & pubslocal & traditional
Savor traditional German breakfast in a giant windmill.
75 min · St. Louis
Overnight: St. Louis
e.g. Drury Inn Union Station · Moonrise Hotel
Day 2 Around St. Louis
🌡 1.1–33.3°C · 🌧 ~19 rain days · ☀ 14.1h light
09:00
The Central West Endmuseums & heritagecoffee & bakes
Savor eclectic dining amid historic mansions and chic boutiques.
90 min · St. Louis
10:30
Missouri History Museummuseums & heritagehistory & sagas
Discover history through exhibits, including a full-scale Spirit of St. Louis.
50 min · St. Louis · Free
open: W-M 10AM-5PM, Tu 10AM-8PM
11:20
Pulitzer Foundation for the Artsmuseums & heritagehiking
Experience contemporary art in an innovative avant-garde space.
50 min · St. Louis · Free
open: W Sa 10AM-5PM, Th F 10AM-8PM
12:10
Anheuser-Busch Brewerycraft beer & pubshistory & sagas
Taste fresh beer samples amidst historic red-brick brewery buildings.
50 min · St. Louis
13:00
Old Courthousemuseums & heritagehistory & sagas
Visit the historic site of the Dred Scott case and view compelling exhibits.
50 min · St. Louis · Free
13:50
Lafayette Square and Parkmuseums & heritagecoffee & bakes
Relax in a park surrounded by charming Victorian homes and cafes.
90 min · St. Louis
15:20
Ted Drewes Frozen Custardhistory & sagas
Delight in rich, creamy frozen custard topped with endless possibilities.
60 min · St. Louis
Overnight: St. Louis
e.g. Drury Inn Union Station · Moonrise Hotel
Day 3 Tulsa
🌡 1.3–36.1°C · 🌧 ~21 rain days · ☀ 13.9h light
16:53
Greenwood Cultural Centermuseums & heritagehistory & sagas
Learn about the history of Tulsa's Greenwood District and enjoy special performances.
50 min · Tulsa
open: M-Sa 9AM-5PM
18:30
Shades of Brownmuseums & heritagelocal & traditionalcoffee & bakes
Enjoy quality coffee amidst rotating local art and live music.
75 min · Tulsa
open: Su-Th 8AM-11PM, F Sa 8AM-midnight
Overnight: Tulsa
e.g. Super 8 Motel - Downtown · Hotel Ambassador
See the remaining 7 days of the 10-day plan →
Route map
Similar journeys
- The Alaska Highway — Dawson Creek → Fairbanks · 8–12 days
- Cabot Trail — 300 km loop · 3–5 days
- Icefields Parkway — Banff → Jasper · 3–5 days