Route 66 Guided Car Caravans

      Chicago, IL, USA

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

      Two Lane America
      • Email address verified

      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:

      • May 18-30 (85% full)
      • June 15-27 (90% full)
      • Aug 24-Sept 5 (10% full)
      • Sept 7-19 (70% full)
      • Sept 21-Oct 3 (70% full)

      2024 Pricing Per Peron:

      $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 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)

      Deposit: $250
      Solo Occupancy

      1 person/1 hotel room

      Deposit: $250

      Available options


      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

      Two Lane America
      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.