Route 66 Guided Car Caravans

Chicago, IL, USA

TL
Two Lane America
  • Email address verified
30 reviews
Duration: 13 days
Group size: 10 - 34
Route 66 Guided Car Caravans
Chicago, IL, USA

Two Lane America
  • Email address verified
30 reviews

Duration: 13 days
Group size: 10 - 34

About this trip

Check the dream off your bucket list with our Route 66 guided caravans..


The fabled “Mother Road” is a bucket-list trip for millions of people. Be one of the Road Warriors that make the dream a reality!

Imagine hitting the pavement on this 13-day trip of a lifetime with zero planning required.

Starting in Chicago, you'll travel in a caravan of no more than 15 cars with turn-by-turn directions, suggested photo stops, dozens and dozens of included activities, and a tour guide with years of Route 66 experience for 13 days of unforgettable fun.

You bring the car or truck of your choice. We'll do the rest.

Dates and Pricing

2025 Dates:

  • May 24-June 5 (SOLD OUT, CONTACT US IF INTERESTED)
  • June 7-19 (WEST TO EAST- THIS TRIP STARTS IN LA AND ENDS IN CHICAGO) (25% full)
  • June 21-July 3 (35% full)
  • Sept 6-18 (50% full)
  • Sept 20-Oct 2 (40% full)

2025 Pricing Per Person:

$2650 per person for dual occupancy ($5300 total), $3250 per person for single occupancy

Want more info?

Have questions? Click here for more info and FAQ about this tour!


We're also always available via austin@2laneamerica.com for any other questions you may have! If you have a specific situation that doesn't fit the regular packages offered, please reach out as well!

Itinerary Basics at a Glance

Trip Start: Chicago, IL

Trip End: Los Angeles, CA

States: 8 (IL, MO, KS, OK, TX, NM, AZ, CA)

Mileage: Approx. 2,400


Day 1: Chicago, IL, Day 2: Chicago to Litchfield, IL, Day 3: Litchfield to St. Louis, Day 4: St. Louis to Springfield, MO, Day 5: Springfield to OKC, Day 6: Oklahoma City, Day 7: OKC to Amarillo, Day 8: Amarillo to Albuquerque, Day 9: Santa Fe Day Trip, Day 10: ABQ to Winslow, AZ, Day 11: Winslow to Grand Canyon to Williams, AZ, Day 12: Williams to Barstow, CA, Day 13: Barstow to LA

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 people/1 hotel room (Be sure to select 2 of these at registration so total equals $5300)

$2,650
Deposit:$250
Solo Occupancy
Deposit:$250

1 person/1 hotel room

$3,250
Deposit:$250

Available options

Pre-Night(s) in Chicago
$334

Includes valet parking, all taxes/fees at the Palmer House (Does not include breakfast)

Post-Night(s) in LA
$245

Includes garage self-parking, all taxes/fees, and breakfast at the Homewood Suites LAX

Route 66 Passport
$23

Many of the places we go have passport "stamps" you can collect in this passport book.



Itinerary

Day 1
Chicago: Beginning of the Trail!

Begin your adventure in America’s third largest city, Chicago, as you meet your fellow travelers for a welcome dinner and trip briefing. This is a perfect opportunity to try Chicago’s famous deep-dish pizza!


Featured Stops: Exchequer Restaurant, "Route 66 Begins" sign

Included Meals: Dinner

Hotel: Palmer House Hilton

Your Organizer


TL
Two Lane America
30 reviews
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

Austin leads trips that are not only fun, but interesting as well...And this one was no exception. Our tour of Sun Recording was nostalgic and wonderful, and our visit to the battlefield at Port Hudson was a view into a slice of history that I had never known about. And so much more...Austin is always respectful of his guests and aims to make our experiences the greatest...Well done!
By Nancy B for Nashville to New Orleans Guided Car Caravans on Nov 13, 2024
We had a great time. Good trip with good people.
By Clifford C for Nashville to New Orleans Guided Car Caravans on Nov 07, 2024
We had a BLAST! Austin was AMAZING. Sooooo many sites and great stops. Food and accommodations were FANTASTIC. We made GREAT FRIENDS. We are already planning another trip with Austin for next year!!
By Tamara H for Route 66 Guided Car Caravans on Oct 12, 2024
We had an amazing time traveling Route 66 with Austin and the group. Accommodations were very comfortable and varied. Enjoyed each of the stops and meeting all of the fine people along the way and getting to know the members of our group better. We liked having plenty of scheduled activities and stops, but also appreciated time on our own. Food was great! We could not have asked for a better tour guide! Austin provided thorough information about the sites we were visiting, suggestions for additional restaurants, and activities we might enjoy on our own. Plus, he had the patience of Job! 🤗
By Larry W for Route 66 Guided Car Caravans on Oct 11, 2024
Great trip, by doing a caravan, we met great people and enjoyed all the stops and driving Route 66. Austin is the greatest tour guide, not only leading us to the the museums and stations and attractions along Route 66 but also letting you know all of the traffic merging ahead of us, coming behind us in our blind spots. All of this while driving the lead car. At every stop he had water and snacks in the back of his van. Food and accommodations were good and Austin took care of any problem with accommodations. Every overnight stay there were plenty of recommendations of where to eat when not part of the tour. We enjoyed the tour so much with Austin that we signed up for a New England tour in 2025 as soon as we got home. Any tour with Two Lane America is highly recommended, you won't be disappointed.
By Leland S for Route 66 Guided Car Caravans on Sep 30, 2024
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