Ride the first 100 miles of Route 66 in the back seat of a restored 1950s or 1960s car, chauffeured by the people who keep it running, from the Begin sign to the museums of Pontiac.
From$249per person
Overview
This is the opening stretch of the road, and the best way to see it is from a car built when it was still US 66. Members of a Chicago-area classic car club drive their own restored sedans and convertibles, three guests to a car, in a convoy of four. Expect chrome, bench seats and drivers who will happily tell you what is under the hood. Road captain Darlene Moss, a former librarian from Pontiac, rides in the lead car and keeps the group together.
The day runs from breakfast at Lou Mitchell's to an afternoon in Pontiac, with the Gemini Giant, a restored Texaco station and a 1932 Standard station along the way. About 200 miles round trip, out on the old road and back on the interstate. Lunch is included. The cars have no air conditioning in summer and roll their windows down instead, which is part of the fun. Bring a light jacket for the morning and a hat for the open cars.
Photos
Itinerary
Lunch is included. Times depend a little on traffic and how long the group lingers at each stop.
Meet at 8:00 at the Begin Route 66 sign on Adams Street, where Darlene matches you with your car and driver. At 8:15 the convoy rolls to Lou Mitchell's on Jackson Boulevard for breakfast, with the free donut holes and Milk Duds it has handed out for decades. At 9:15 we head southwest on Ogden Avenue and the old road through the suburbs, with a slow pass of the neon sign at Dell Rhea's Chicken Basket in Willowbrook. At 10:30 we reach Joliet for the Route 66 welcome center in the Joliet Area Historical Museum. At 11:30 the Gemini Giant, a fiberglass astronaut nearly 30 feet tall, in Wilmington. At 12:20 Ambler's Texaco in Dwight, pumping gas from 1933 until 1999, and at 12:50 the restored 1932 Standard station in Odell. Lunch at 13:30 at the Old Log Cabin in Pontiac. From 14:30 two hours for the Route 66 Hall of Fame and Museum, the Pontiac-Oakland Automobile Museum and the murals. Leave at 16:30 for the interstate and arrive back in downtown Chicago about 18:30.
Pace: RelaxedTwo to four hours on the road on most days, long stops, short level walks in towns and at roadside sights. Every stop is optional; you can always stay with the vehicle.
Route map
Map tiles © Esri, HERE, Garmin, map data © OpenStreetMap contributors. Straight lines join the stops; the trip follows the old Route 66 alignments between them.
Route at a glance
Road miles are rounded and include the detours to the stops named in the itinerary.
| Day | From and to | Miles | On the road |
|---|---|---|---|
| The day | Downtown Chicago | 200 | Joliet, Wilmington, Dwight, Odell, Pontiac and back |
| Total | 1 day | 200 | Illinois |
Already included
Lunch, the vehicle and a road captain, 1 entries and guided visits
Straight talk
Dates and prices 2026-27
Per person in US dollars, lunch included. Group up to 12 guests.
| Date | Status | PricePer person |
|---|---|---|
| Saturday | Available | $249 |
| Saturday | Guaranteed | $249 |
| Saturday | Available | $249 |
| Saturday | Available | $249 |
| Saturday | Few seats | $249 |
| Saturday | Available | $249 |
| Saturday | Available | $249 |
Guaranteed means enough guests have booked and the departure will run. Seats change every week. Email [email protected] and we hold a seat for 72 hours. All departures on one page.
Practical
Weather in Illinois
Spring is cool and showery, summer hot and humid with short storms, fall dry and mild; winter brings snow and ice
Time zone
Central Time, with daylight saving time from March to November
Where it starts and ends
Start: Meet at the Begin Route 66 sign, Adams Street, 8:00. End: Back in downtown Chicago about 18:30.
What to eat
Lou Mitchell's breakfast, Dell Rhea's fried chicken, a Cozy Dog and a horseshoe sandwich in Springfield, Funks Grove maple sirup, a meal at the Ariston Cafe in Litchfield
What to bring
Comfortable shoes, a hat, sunscreen and a light jacket. There is space in the vehicle for a small bag.
Your road captain
Illinois and Missouri
Darlene was a small-town librarian in Pontiac for 25 years and helped catalog the collection at the Route 66 Hall of Fame. She leads the Illinois and Missouri trip and the museums trip.
Road captains rotate on some dates; the name for your departure is in your documents. Meet all the road captains
FAQ
Booking, motels, flights and insurance questions are answered on the main FAQ page.
No. The cars belong to club members, who drive them themselves. If you want to drive a classic yourself, look at our convertible trips, where guests take the wheel.
Members of a Chicago-area classic car club who restore and show their cars. They are volunteers who love the road, and the club receives a donation from every booking. Each car carries three guests, so couples are usually paired with one other guest.
They are fully restored and inspected before each season, with lap belts and, in most, shoulder belts added. Rides are a little bouncier than a modern car and summer days can be warm without air conditioning. Booster seats are not possible in most models, so the minimum age is 8.
We go in light rain with the tops and windows up. If heavy storms are forecast, the club may swap convertibles for hardtops, and in severe weather we move you to another date or refund you in full.
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Ask about dates
Email us the date you like, how many of you are traveling. We hold the seat for 72 hours while you decide.
Ask about datesBookings, dates and free seats
What to include
We reply Monday to Friday, 8:00 to 17:00 Central Time, usually the same working day.
We use what you send only to answer you and to arrange your trip. See our privacy policy.
From$249
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