Route 66 Guided Car Caravans

Chicago, IL, USA

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

Two Lane America
  • Email address verified
85 reviews

Duration: 13 days
Group size: 10 - 42

About this trip

Dates and Pricing

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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
RT66 VIP Gift Box
$80


Itinerary

Day 1
Chicago: Beginning of the Trail!

Your Organizer


TL
Two Lane America
85 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

This trip totally exceeded our expectations. Austin is the best!!!!!!!!! His attention to details and knowledge is impeccable. The size of the group was just perfect. The places we saw and the people we met were fantastic. The accommodations were top notch. This trip wasn't just about seeing wonderful places but also learning about the history of each stops along the way. We look forward to booking another trip with Austin in the near future. Way to go!
By Christa A for Route 66 Guided Car Caravans on Oct 12, 2025
Austin is a fabulous tour guide. He introduced us to all things Route 66, from the beginning point in Chicsgo, to the end point at Mel's Diner in LA. The trip was filled with special experiences, and we met many interesting folks who maintain Route 66 businesses along the way, and have connections to the Route 66 story. The accommodations and meals were great. The suggestions for personal sightseeing were on point. And we met wonderful people who were part of our tour. We would highly recommend this trip and look forward to traveling with Two Lane America again!!
By Mary Jo Y for Route 66 Guided Car Caravans on Oct 11, 2025
Fantastic trip! If you are considering a driving, caravan type trip, 2 Lane America would be hard to beat. Austin Coop is excellent at all facets of the drive. His knowledge and tour guide abilities are second to none; plus, he is a nice guy. If you are considering 2 Lane for a trip, go for it!
By James C for Route 66 Guided Car Caravans on Oct 11, 2025
We had a fantastic trip! Austin was an awesome guide and the route and sites we visited were really enjoyable. Our accommodations were all very good and the folks we met and traveled with made it all quite memorable. We’ll be adding another trip with Two Lane America to our itinerary for 2026.
By Todd S for Route 66 Guided Car Caravans on Oct 09, 2025
Great trip. Smooth running, lots of different things going on, kept us up to date on the next thing happening, very nice lodging and food choices.
By Michael H for Route 66 Guided Car Caravans on Oct 07, 2025
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