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Chicago Route 66 Multi-Day Tour 14 Days

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Rated on 1 provider · Why

  • Chicago
  • 14 days
  • Updated November 2, 2026

Follow Route 66 from Chicago to Los Angeles on a 14-day self-guided journey past 450+ points of interest across eight states.

About this tour

Set out from Chicago and follow the legendary Route 66 west to Los Angeles on a 14-day road trip through the heart of America. This self-guided experience features more than 450 handpicked points of interest across eight states, giving you room to shape the journey at your own pace.

Use the downloadable audio-guide map on your smartphone to explore iconic landmarks, historic towns, scenic detours, hidden gems, classic diners, and memorable landscapes. Offline content helps you avoid roaming charges along the way. The route starts at the historic Route 66 Begin Sign at E Adams St and S Michigan Ave in Chicago, where the highway’s story begins.

Discover the places and roadside character that made Route 66 a symbol of adventure. Download your guide and start exploring Chicago Route 66, one stop at a time, all the way to Los Angeles.

Highlights

  • Explore more than 450 handpicked points of interest
  • Travel Route 66 across eight states, from Chicago to Los Angeles
  • Discover historic towns, iconic landmarks, and scenic detours
  • Find classic diners, hidden gems, and sweeping landscapes

What's included

Included

  • Tour activation link
  • Offline tour content to help avoid roaming charges
  • Downloadable audio-guide map for your smartphone in multiple languages

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

Important information

  • Wheelchair accessible
  • Infants and small children can ride in a stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • The route begins at the Route 66 Begin Sign at E Adams St and S Michigan Ave in Chicago

How this score is calculated

This tour has no TourTruth score yet: Viator doesn't show a usable rating for it. It gets a score as soon as a provider lists one.

How the score works
  • Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
  • Listings on different providers are combined in proportion to their review counts.
  • Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
  • The result is shown from 0 to 10. Tours without a usable provider rating are not scored.

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