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HomeDestinationsRoute 663-Day Itinerary

AI-Generated Itinerary

3-Day Route 66 Itinerary

Your complete day-by-day guide to Route 66 — handpicked attractions, dining recommendations, and local tips for an unforgettable 3-day trip.

3 DaysRoute 66AI-CuratedFree & Personalised
3 days · 12 activities · Flexible plan
Personalise with AI
1

Day 1

Chicago Begin Sign to Springfield, Illinois (about 200 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 9:30 AM

Photo at the Route 66 Begin sign

Start at Adams Street and Michigan Avenue for the classic photo, then have breakfast at Lou Mitchell's on Jackson Boulevard.

Late Morning

9:30 AM - 1:00 PM

Joliet and the Gemini Giant

Drive southwest about 60 miles (1.5 hours with city traffic) via Joliet to Wilmington's towering Gemini Giant spaceman statue.

Afternoon

1:00 PM - 5:30 PM

Pontiac museum and Atlanta's giant

See the Route 66 Hall of Fame and Museum in Pontiac and the Paul Bunyon giant in Atlanta, then drive about 140 miles (2.5-3 hours) to Springfield.

Evening

5:30 PM - 9:00 PM

Corn dogs in Springfield

Eat at the Cozy Dog Drive In, a Route 66 landmark since 1949 that claims to have invented the corn dog on a stick.

2

Day 2

Springfield to Springfield, Missouri via St. Louis (about 300 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:00 AM

Chain of Rocks Bridge

Drive about 100 miles (1.5-2 hours) to the bridge and walk to its famous 22-degree bend over the Mississippi.

Late Morning

10:00 AM - 1:00 PM

Gateway Arch and frozen custard

Ride the tram up the 630-foot Gateway Arch (book timed tickets), then stop at Ted Drewes for a concrete of frozen custard.

Afternoon

1:00 PM - 5:30 PM

Ozarks drive via Cuba

Follow I-44 and old 66 about 215 miles (3.5-4 hours), stopping for the murals in Cuba and the giant rocking chair near Fanning.

Evening

5:30 PM - 9:00 PM

Cashew chicken in Springfield, Missouri

Try Springfield-style cashew chicken, the city's unique fried-chicken take on a Chinese-American classic.

3

Day 3

Kansas Corner to Oklahoma City (about 290 miles)

4 activities · ~8 hrs

Morning

7:30 AM - 10:30 AM

Carthage, Galena and Kansas

Drive through Carthage, Missouri, then Galena, Kansas, where a rusty tow truck inspired a character in the movie Cars.

Late Morning

10:30 AM - 1:00 PM

Blue Whale of Catoosa

Photograph the smiling blue whale on its pond near Tulsa, one of the road's most beloved roadside attractions.

Afternoon

1:00 PM - 5:00 PM

Arcadia's Round Barn and POPS

Continue on the old road to Arcadia's 1898 Round Barn and POPS, with its 66-foot neon soda bottle and hundreds of sodas.

Evening

5:00 PM - 9:00 PM

Steak in Stockyards City

Have dinner at Cattlemen's Steakhouse, an Oklahoma City institution since 1910 in the historic Stockyards City district.

AI Personalisation

Make this itinerary yours

Tell Lizza your budget, interests, and travel style. She'll fine-tune this 3-day Route 66 plan with personalised recommendations, tips and more.

  • Personalised recommendations
  • Tailored to your travel style
  • Updated in real time
Chat with Lizza AI

Trip at a Glance

  • Route 66, United States
  • 3 days
  • Fast-pacedPacked with highlights — ideal for a quick, efficient visit.

Other Itineraries

  • 5-Day Route 66 ItineraryMore time, more experiences
  • 7-Day Route 66 ItineraryExplore beyond the city
  • 10-Day Route 66 ItineraryThe ultimate getaway

Quick Tips

  • Book accommodation at least 2 weeks in advance
  • Get travel insurance before departure
  • Check visa requirements for your passport
  • Download offline maps before arrival
  • Notify your bank of your travel dates

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