Tours
‘The Centennial Tour’: (2026)
Group Tour from Chicago to Los Angeles – April 2026
Duration: 26 days
Gilligans ‘Official Tour’ is our premium 26 day, fully-guided group tour, with just 15 cars/couples attending.
In 1926, Route 66 was but one of the highways designated under the U.S Highways Act of 1926. Route 66 will celebrate it’s 100th birthday in 2026 – we invite you t be part of it!
As part of our ‘Official Tour’ you will clock up an average of just 145 miles (233km) 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 – there is simply no better way of doing it.
Although you’re part of a group – you’re still driving yourself – and still free to explore as you go.
TOUR FORMAT:
Following breakfast, your day usually starts with a morning briefing to outline the day ahead, give an overview about the areas visited and to answer questions.
The group generally departs around 8:30am, and often arrives at the hotel at about 4:30 each afternoon. Some days are shorter – others slightly longer. Time spent driving is approx 2.5-3hrs per day, which allows more time to see what you came to see: Route 66!
Along the way, guests use our GPS platform and extensive Route Book to learn about towns and notable sites as you drive.
We travel as a group – although not in a ‘convoy’ as such – giving guests more freedom to stop for more or less time (dependent on interests) at the places we visit.
Gilligans also plan a few stops along the journey each day that really do provide a personal insight into the history of the ‘Mother Road’…
US$8,295* per person (INCLUDES FLIGHTS)
*Approx pricing dependent on flight costs / departure city.
NASCAR + Route 66:
Self-Drive from Chicago to Los Angeles – July 2025
Duration: 27 days
LIMITED TO JUST 15 DOUBLE TICKETS!!!
Here’s a chance for motorsport fans to be in the heart of the action at the 2025 edition of Chicago’s NASCAR race weekend!
Join us on a high-octane, 26 day tour that kicks off at full bore; you’re straight down trackside and into prime ‘reserved’ seating at this 12-turn, 3.6 kilometre street circuit.
Feel the slipstream as these V8 monsters kick up a storm in the Windy City!
That the course includes a section of fabled Route 66 is appropriate, because when the racing and the partying is done, you’ll be heading across America’s ‘Mother Road’ for an amazing, 21 day road-trip to Los Angeles via the Grand Canyon, along with THREE great nights in Fabulous Las Vegas!
This fantastic tour commences on July 2nd upon check-in at your Chicago Hotel.
Enjoy some free days exploring Chicago, along with the opportunity to be part of the July 4th / Independence Day celebrations throughout the city!
Saturday and Sunday is all about the Racing! TWO brilliant days in outstanding reserved seats provide effortless viewing of both days of racing.
Once the weekend of NASCAR racing is over – you’ll collect your rental car and set off for Los Angeles – via historic Route 66, enjoying 21 nights across heartland America!
US$7,995 per person
(NOTE: Flights not included)
Route 66: Self-Drive Tour
Chicago to Los Angeles (pre-planned by Gilligans)
Duration: 20 days (includes 3 nights in Las Vegas!)
Gilligans also offer ‘Self-Drive Tour’s.
These are for individuals who wish to see Route 66 for themselves, whenever they determine.
You tell us the date you wish to depart Chicago – we will take care of the rest!
US$5,595pp
(NOTE: flights not included)