Route 66 Guided Car Caravans

      Chicago, IL, USA

      TL
      Two Lane America
      • Email address verified
      16 reviews
      Duration: 13 days
      Group size: 10 - 36
      Route 66 Guided Car Caravans
      Chicago, IL, USA

      Two Lane America
      • Email address verified
      16 reviews

      Duration: 13 days
      Group size: 10 - 36

      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

      2024 Dates:

      • Aug 24-Sept 5 (15% full)
      • Sept 7-19 (80% full)
      • Sept 21-Oct 3 (80% full)

      2025 Dates:

      • May 24-June 5
      • June 7-19 (WEST TO EAST- THIS TRIP STARTS IN LA AND ENDS IN CHICAGO)
      • June 21-July 3
      • Sept 6-18 
      • Sept 20-Oct 2

      2024 and 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)

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

      $2,650
      Deposit: $250
      Solo Occupancy

      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
      16 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

      If you truly want to see all the great stops along Route 66 in your own ride, this is definitely the way to go. Austin of Two Lane America runs a fantastic organized Itinerary. Everyone in my tour group had a great time. This trip should be a bucketlist item for anyone who loves American nostalgia as much as their car.
      By Nick L for Route 66 Guided Car Caravans on Jul 06, 2024
      What a great experience! Well planned; Austin had all the details attended to and many pleasant surprises as the trip progressed. I would recommend this experience to anyone who is interested in Route 66; very few can say they have been from one end to the other with pictures, and documents to prove it. You become friends with a diverse group of fellow travelers. Definitely 5 Stars!
      By Frank E for Route 66 Guided Car Caravans on Jul 04, 2024
      Thirteen days of fun and awe with great people! Austin took care of everything and then some. What an amazing tour guide and host! I simply cannot overstate that. This was a wonderful experience to have shared with my teenaged son (it was his idea) and I am so grateful we did it . . . with Austin. Most know about Route 66 but relatively few have driven its entire length. This trip was incredibly special. Do something unforgettable and ride the Mother Road!!!
      By Cindy C for Route 66 Guided Car Caravans on Jul 03, 2024
      My trip was awesome! When the original bus booking was cancelled, Austin made room for me in the lead vehicle of the car caravan. I felt like I was part of a private tour. Everyone on the trip was treated with respect and responded in the same fashion. The camraderie was wonderful. We were a 'family' by end of trip. The tour stops were well-chosen and reflected the spirit of "Route 66' Ample time was allowed to browse/shop at every location. Austin shared interesting information about each stop that made it more enjoyable. I'd recommend Two Lane America to anyone who prefers an 'adventure' instead of just a trip.
      By Kathy R for Route 66 Guided Car Caravans on Jun 29, 2024
      We had an absolutely wonderful experience on our Route 66 tour this past May. The trip allowed us to relax and enjoy our trip with Austin at the helm while meeting and making friends with some amazing people from all over the US. Couldn't have done half of the things we did on our own. Austin is an amazing tour guide. He is knowledgeable about all things Route 66 and knows so many people on the Route allowing us to see so much. This trip exceeded all of our expectations. Look forward to Joining Austin and Two Lane America in other tours in the near future. Highly recommend Austin and Two Lane America!! Mike and Rachele
      By Michael M for Route 66 Guided Car Caravans on Jun 16, 2024
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