Six unhurried days on the first 500 miles of Route 66, from Lou Mitchell's in Chicago through Lincoln's Springfield and across the Mississippi to the Ozark hills, led by a former Pontiac librarian.
From$2,190per person, double room
Overview
This is our gentlest section trip and the one most people take first. The first two Route 66 states are farm country and river towns, with more restored gas stations per mile than anywhere else on the road and short drives between them. No day runs longer than about 130 miles. You sleep in Chicago, Pontiac, Springfield, St. Louis and Cuba, and the trip ends at the Springfield-Branson airport in the Missouri Ozarks.
Darlene Moss leads it. She was a small-town librarian in Pontiac, she knows the volunteers who keep the little museums open, and she can tell you which pie is worth the stop. Meals include breakfast daily, lunch at Dell Rhea's Chicken Basket, the Cozy Dog and the Ariston Cafe, and both the welcome and farewell dinners. Late afternoons stay free for a nap, a walk or a slice of that pie.
Photos
Itinerary
Meals: B breakfast, L lunch, D dinner. Day 1 is arrival day; flights to the start are optional.
Take a taxi or the Blue Line from O'Hare to the hotel on Michigan Avenue, about 45 minutes. Darlene Moss meets the group in the lobby at 5:30 pm. She walks you around the corner to the Begin Route 66 sign on Adams Street, close to where the road started at the lakefront in 1926, with the Art Institute lions across the avenue. Welcome dinner follows in the Loop, along with a short talk on the five days ahead and the roadside stops that matter most to her.
Breakfast at Lou Mitchell's, open since 1923, where the coffee arrives before you ask. Lunch at Dell Rhea's Chicken Basket in Willowbrook, frying chicken beside the old road since the 1940s. Joliet's Route 66 Welcome Center comes next, then the Gemini Giant at the Launching Pad in Wilmington. Two restored stations follow: Ambler's Texaco in Dwight, which sold gas from 1933 until 1999, and the 1932 Standard station in Odell. In Pontiac by 4 pm, Darlene's evening walk covers the murals and the swinging bridges over the Vermilion River. About 105 miles.
Morning at the Illinois Route 66 Hall of Fame and Museum, where the painted van and school bus of the artist Bob Waldmire sit out back. His father Ed invented the Cozy Dog, and that is where lunch is today. On the way south, Funks Grove sells maple sirup, spelled the old way, from a shed in the trees, and Atlanta has a giant holding a hot dog beside its octagonal 1908 library. Afternoon at the Lincoln Home in Springfield. About 100 miles.
Lincoln's Tomb at Oak Ridge Cemetery after breakfast, where visitors rub the nose of the bronze bust for luck. South to Litchfield for lunch at the Ariston Cafe, in business since 1924, then the little 1926 Soulsby Shell station in Mount Olive. Late afternoon you walk out over the Mississippi on the Chain of Rocks Bridge, a mile long with a bend halfway across. Evening in St. Louis, with a stop at Ted Drewes for a concrete of frozen custard. About 110 miles.
A short drive, about 85 miles, southwest from St. Louis into the hills. At Stanton the guided tour of Meramec Caverns takes about 80 minutes on lit paths underground. Afternoon in Cuba, where Darlene leads a walk to the murals, including Amelia Earhart's unplanned landing near town in 1928 and Bette Davis stopping at a local hotel in 1948. Four miles west, a rocking chair 42 feet tall stands at Fanning. Farewell dinner in town, then a night in a stone cottage at the Wagon Wheel Motel.
West past Rolla to Devils Elbow, where the 1923 bridge crosses the Big Piney below limestone bluffs and the Elbow Inn sits by the water. In Lebanon, the Munger Moss Motel sign and the small Route 66 museum inside the town library. Springfield by early afternoon: the Birthplace of Route 66 Roadside Park and the city square where the road's number was settled in 1926. Springfield-Branson airport is about 15 minutes away; book flights leaving after 4 pm. About 130 miles.
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 |
|---|---|---|---|
| Day 1 | O'Hare airport to Chicago | 20 | Airport transfer |
| Day 2 | Chicago to Pontiac | 105 | Joliet, Wilmington, Dwight, Odell |
| Day 3 | Pontiac to Springfield, Illinois | 100 | Funks Grove, Atlanta, Lincoln |
| Day 4 | Springfield, Illinois to St. Louis | 110 | Litchfield, Chain of Rocks |
| Day 5 | St. Louis to Cuba | 85 | Meramec Caverns, Ozark foothills |
| Day 6 | Cuba to Springfield, Missouri | 130 | Devils Elbow, Lebanon |
| Total | 6 days | 550 | Illinois, Missouri |
Where you stay
Rooms by town and style. The exact motels and hotels for your date, these or similar ones, are confirmed in your travel documents.
1 night
4-star hotel on Michigan Avenue facing Grant Park, or similar
1 night
Small hotel at the Pontiac exit, five minutes from the courthouse square, or similar
1 night
Historic downtown hotel near the Old State Capitol, or similar
1 night
Hotel near Forest Park, or similar
1 night
Wagon Wheel Motel, stone cottages from 1936, or similar
Already included
5 nights, 5 breakfasts, 3 lunches, 2 dinners, 2 entries and guided visits
Straight talk
Dates and prices 2026-27
Per person in US dollars, sharing a double room. Group up to 14 guests.
| Dates | Status | Double roomPer person | Single roomPer person |
|---|---|---|---|
| to Sunday arrival | AvailableEarly booking: save $150 | $2,190 | $2,730 |
| to Sunday arrival | GuaranteedEarly booking: save $150 | $2,190 | $2,730 |
| to Sunday arrival | AvailableEarly booking: save $150 | $2,190 | $2,730 |
| to Sunday arrival | AvailableEarly booking: save $150 | $2,190 | $2,730 |
| to Sunday arrival | Few seatsEarly booking: save $150 | $2,190 | $2,730 |
| to Sunday arrival | AvailableEarly booking: save $150 | $2,190 | $2,730 |
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.
Optional add-on
Economy on scheduled airlines into Chicago O'Hare International Airport (ORD) and home from Springfield-Branson National Airport (SGF), per person including taxes. Add them when you book, or fly on your own and meet us on day 1.
Fares are held for 72 hours with your seat and confirmed when you pay the deposit. Extra nights before or after the trip on request.
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
Weather in Missouri
Spring is mild and wet, summer hot and humid, fall dry and colorful in the Ozarks; winter can bring ice on the hill roads
Time zone
Central Time, with daylight saving time from March to November
Where it starts and ends
Start: Chicago O'Hare International Airport (ORD). End: Springfield-Branson National Airport (SGF).
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
Luggage
One medium suitcase and a small bag per person. Vintage motel rooms are compact and some have no elevator.
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.
Two to three hours of actual driving, spread across the day. Distances run from 85 to 130 miles, and there is a stop every 30 to 45 minutes, because the towns in Illinois and Missouri sit close together.
Not much. The longest walks are the Chain of Rocks Bridge, about a mile on a flat deck, and the Meramec Caverns tour, a little over a mile on lit paths with some steps. You can skip either one and wait with the coach.
It is where Route 66 got its number, and the Springfield-Branson airport has direct flights to several hubs. It also sets you up to continue west: Tulsa is about 180 miles away, and our Oklahoma and Texas trip starts there.
Yes. Some dates of the Oklahoma and Texas trip start a week or two later, and a trip advisor can book the hotel nights and a car or transfer from Springfield to Tulsa in between.
April and October are cool and pleasant, with highs in the 60s. May, June and September are warm. July is hot and humid in Missouri, so the July date keeps the walks to the morning.
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