Tours

28 Day GROUP TOUR

Chicago to Los Angeles:

Gilligans ‘Official Tour’ is our premium 28 day, fully-guided group tour.

As part of our ‘Official Tour’ you will clock up an average of just 144 miles (230km) each day on the road!  This is less than any other tour we know of, and allows you time to explore as much of Route 66 as you can handle.

Gilligans runs just two tours a year, one in mid-April, and another in mid-September.

If you’re serious about doing Route 66 right then there is simply no better way of doing it.

Although you’re part of a group, you’re still driving yourself and you’ll explore Route 66 with stops that interest you both.

20 Day Self-Drive Tour: Chicago to Los Angeles

Perfect for those who wish to see Route 66 for themselves & whenever it suits your schedule.

You tell us the date you wish to depart Chicago and we’ll take care of the planning!

Fly into Chicago’s O’Hare airport from anywhere in the world – and your hotel room will be waiting!

On the morning of departure:

You’ll be collected from your downtown hotel and dropped off to collect your rental car.

Once behind the wheel – you will follow our extensive Route Book & APP all the way to Los Angeles via Historic Route 66, the Grand Canyon & a TWO night stay in “Fabulous Las Veggas”!

NOTE: Flights are your responsibility:

ARRIVAL: Chicago O’Hare (ORD)

DEPART: Los Angeles (LAX)