Route 66 Guided Car Caravans

Chicago, IL, USA

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

Two Lane America
  • Email address verified
47 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
$2,650
Deposit: $250
Solo Occupancy
Deposit: $250
$3,250
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
47 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

I have dreamed of driving Route 66 for along time, but until I found Austin Coop and Two Lane America I didn't have a plan. The trip as described on Austin's website sounded like it would be just the ticket for a great trip. We were able to take this trip, Austin's first West to East version if his iconic Route 66 trip, with two long time friends and met two other couples who fast became friends as well. When we first met Austin in LA, we knew right away this was going to be a great trip. Austin is very authentic and you can tell right away that he loves guiding these trips and his first priority is each of us on the trip. He is very organized and knows the route so well that he can adapt on the go and still make it seamless. From our first stop at Santa Monica to the end of the route in Chicago we were introduced to special guests along the way that have been involved with Route 66 for many years. They had great stories from the road that enhanced the trip. Many of the museums we visited were hosted by the owners who had lovingly restored buildings and collected artifacts and spent time with us (sometimes even opening up just for us). These are some of the things that made this trip so much better than anything I expected. Austin has nurtured his relationships with so many people on the route, you can tell their friendship with Austin was extended to each one of us on the trip. Many of these people could be considered "Godfathers of Route 66" because of their knowledge and experiences. While Austin's knowledge and experiences are extensive, he declined to be considered one of the "Godfathers" so we called him the "Godson of Route 66". Austin has taken great care to use accommodations that would offer the same guest experience that he was providing to us. There were never any issues with reservations or rooms, Austin was always making sure that everything was right. We quickly learned that Austin has seen just about everything on these trips and always had a way to take care of most anything that came up or put you in touch with someone that could help. Everyday was an adventure and Austin ensured that the day was planned with enough time for visiting the various sites we would see, with rest breaks when needed, and not too many miles each day. At every stop, Austin had water and snacks available for us. He provided radios so we could keep in touch while we were on the road and used that time to tell us stories about the area we were traveling through. This trip was so much more than I expected. There is no way you can see everything we saw without a guide who knows where all the gems are hidden and knows all of the people that make Route 66 so special. And I can't imagine there is a guide with more experience, with more connections with the people, and who cares more for his guests on the trip than Austin Coop. My wife and I are looking forward now to other trips that Austin guides. This was a "once in a lifetime experience" and we can't wait for the next one.
By Jeff R for Route 66 Guided Car Caravans on Jul 31, 2025
Absolutely AWESOME!! The best guided road trip I’ve ever been on. Austin is extremely knowledgeable and had all the arrangements and accommodations scheduled in advance. I was planning on doing Rt 66 myself and came across his add. Glad I signed up, we stopped at places I wasn’t even considering. Big mistake on my part. This is a road trip everyone should take at least once. I would definitely use Two Lane America again.
By Tony M for Route 66 Guided Car Caravans on Jul 16, 2025
Austin makes the trip stress free and fun !!!
By Rick T for Route 66 Guided Car Caravans on Jul 14, 2025
Thoroughly enjoyed the entire adventure. From the initial start to the end of the tour. The places we saw and experienced to the new friends we made all added to lifelong memories we made along the way. Can’t say enough about our host Austin for all the planning he put into the day to day adventures. Would highly recommend the tour venue to any one looking for adventures. THANK YOU😎
By G Douglas W for Route 66 Guided Car Caravans on Jul 13, 2025
The trip was Fantastic! I was planning the trip myself until I ran across Two Lane America. Austin's knowledge of RT 66 added so much more than I could have planned myself. The accommodations were great and I look forward to booking another Caravan with Two Lane for the New England trip this fall. JT
By Joe T for Route 66 Guided Car Caravans on Jul 08, 2025
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