Route 66 Guided Car Caravans

Chicago, IL, USA

TL
Two Lane America
  • Email address verified
77 reviews
Duration: 13 days
Group size: 10 - 42
Route 66 Guided Car Caravans
Chicago, IL, USA

Two Lane America
  • Email address verified
77 reviews

Duration: 13 days
Group size: 10 - 42

About this trip

Dates and Pricing

Want more info?

Itinerary Basics at a Glance

Other trips offered by Two Lane America:

What’s included

  • All hotel accommodations
    13 nights of quality hotels including 2 historic hotels!
  • 18 meals
    13 breakfasts, 2 lunches, 3 dinners
  • All group activities
    Multiple museums, 3 national parks, tons of old filling stations, and more!
  • Guide in lead car
    Route 66 expert guiding you the whole way to LA
  • and much more...
    Trip tote bag, All parking fees and highway tolls, Souvenir-quality guide book, Guided tour of Santa Fe, NM, On-the-road snacks/water, Custom Spotify music playlists, shuttle buses in STL and LA

What’s not included

  • Fuel
    budget about 1 tank every 1.5 days
  • Any meals not mentioned
    did you really want to eat with us each night anyway?
  • Souvenirs
    and believe us, you'll buy a bunch!

Available Packages

Dual Occupancy (per person)
Deposit: $250
$2,750
Deposit: $250
Solo Occupancy
Deposit: $250
$3,350
Deposit: $250

Available Add-Ons

Pre-Night(s) in Chicago
$334
Post-Night(s) in LA
$245
Route 66 Passport
$23
Route 66 Mirror-hanging Air Freshener
$2
RT66 VIP Gift Box
$80


Itinerary

Day 1
Chicago: Beginning of the Trail!

Your Organizer


TL
Two Lane America
77 reviews
OVER 1 MILLION MILES AND COUNTING! For the better part of a decade, Two Lane America has been on the road in some capacity with Route 66 always being a cornerstone of our travels. Austin Coop, founder and lead tour guide, has personally traversed the 2,400+ miles of Route 66 dozens and dozens of times. His love for the Mother Road led to lifelong friendships and partnerships with the small businesses and funky roadside attractions along the way.

Reviews

My wife and I had a wonderful trip on our Route 66 trip from Chicago to Santa Monica with Austin Coop! the trip was not only scenic and historic but also so organized and beyond our expectations. Austin and Two Lane America make this adventure easy and fun. He is so organized and has such extensive knowledge of the entire route along with introductions to experts and local guides and historians along the way. I would 100% recommend this trip to anyone who is considering driving "The Mother Road"
By Arlen f for Route 66 Guided Car Caravans on Sep 28, 2025
Two Lane America offers phenomenal travel trips! In this case, it was a Route 66 car caravan with 17 vehicles and 30 people. The sights we saw and visited were awesome! The days were enjoyable and filled with driving, insights, scenery, commentary, and fun! Speaking of the insights and commentary, Austin has such a deep understanding of the history of Route 66 and connection to the people there! Our fellow travelers were wonderful! They were a joy with which to share the trip. And the surprises and extras that Two Lane America provides were over the top! Highly recommend Two Lane America for their service on any of their itineraries!
By Chuck K for Route 66 Guided Car Caravans on Sep 23, 2025
We really enjoyed the trip, it was well planned and the accommodations were great! I will be taking additional trips with Two Lane America I would recommend this trip!
By Al H for Route 66 Guided Car Caravans on Sep 23, 2025
the route 66 bus trip that i took was the best bur tour i have done Austin was the best tour guide if i could give it a 10 i would had so much fun and learned so much glad i did it. never know Austin i might be back so you better be doing the tour.
By Donna D for Route 66 Guided Bus Tours on Sep 20, 2025
Our dream bucket list Route 66 trip exceeded our expectations!! It was amazing! Austin’s attention to detail, concern for everyone’s comfort, knowledge of the entire route, and his passion for the Mother Road made this a remarkable experience!
By Anita C for Route 66 Guided Bus Tours on Sep 18, 2025
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