Self-Drive Route 66
Chicago to Los Angeles (20-days)
US$5,895
per person – TWIN SHARE
Price Includes:
All accommodation!
Rental Car: Inclusive of insurances and one-way fees (upgrades to convertible or similar based on availabilty)
Gilligans’ 165+ page Route Book & daily itinerary!
iPhone – with free international calling, free text and data; along with Gilligans’ ‘Turn by Turn Navigation’ across old Route 66
The BEST of Route 66: Start in Chicago – finish in Los Angeles!
You’ll drive the best old alignments and spend very little time on the Interstate.
(*pricing subject to change)
Explore Route 66 when it suits YOU!
Gilligans’ ‘Self-Drive Tour’ of Route 66 will allow you to enjoy Route 66 as if you’ve planned it yourself (and very likely, for less money too) with our well-proven and well planned ‘self-drive tour’!
Spend twenty memorable days from Chicago to L.A on what was Historic Route 66… There is no need to plan, no need to research – just turn up!
It’s a complete package: The tour includes all accommodation, a great rental car and our 165+ page Route Book, giving you town-by-town information, historical stories and prompts for navigation.
Each day is made easy by plugging in the Gilligans’ iPhone and following our turn-by-turn APP.
You’ll cross eight states and more than 2,448 miles as you cruise to California, enjoying additional stops at the Grand Canyon and a 2-night side-trip to the Entertainment Capital of the World: Fabulous Las Vegas!
Relax outside at famous motels, and explore the towns, places and iconic points of interest; that have made Route 66 so famous…
Added to this, we’ll be in regular contact to offer suggestions, provide further insight to each day’s visits and ensure that any questions you’ve got along the way get answered!
How do you book?
You only need to tell us the date you want to set off from Chicago – and we’ll take care of the rest!
This is a truly memorable 20-day odyssey that will provide lifelong memories.
It’ll take you back to a simpler time… Today, Historic Route 66 is a living, breathing time-capsule of American culture and history.
Gilligans invites you to take the ‘Highway that’s the Best’ and get YOUR kicks, on Route 66!
Get in contact and secure your Route 66 Self-Drive tour for 2026 TODAY!
(NOTE: Due to the cold USA winters – we suggest travelling from May-October)
“Without question – THE BEST TOUR of Route 66 available in the world” – Kevin Mueller (Blue Swallow Motel Owner – 2019)
Secure your Self-Drive Tour TODAY!
What’s included
- Quality accommodation – including (most with breakfasts)
- One nights accommodation in Chicago (prior to departure)
- Car hire: Premium car or SUV – Inclusive of Insurances and ‘One-Way’ fees (upgrades to convertible or similar available subject to availability)
- Gilligans’ exclusive ‘turn by turn’ navigation programme across Route 66
- Gilligans’ comprehensive Route Book with over 150 pages of town by town notes for your journey!
- Gilligans iPhone with unlimited international calls, free texts & data!
Extras
- Airfares to Chicago / home from Los Angeles
- Rental car upgrades (if any – subject to availability)
-
Travel / Medical Insurance
- Fuel costs (approx US$400 for the entire journey)
- Lunches & Dinners + some breakfasts (eg. Las Vegas)
Conditions
- Driver/s must be over the age of 25 and hold a valid full driver’s license from your home country
- All participants must have relevant travel insurance for the USA
Contact us for a brochure