Small groups of up to 14, a road captain on every trip

How to book
Ambler's Texaco, a small white station with two red pumps on Route 66 in Dwight, Illinois

State 1 of 8, driving west

Illinois Route 66: Chicago, Pontiac and Springfield

Illinois is where every westbound trip on the Mother Road begins: a sign on Adams Street, a diner breakfast, then 300 miles of prairie towns, old gas stations and Lincoln country on the way to the Mississippi.

Trips
61 only in Illinois
Stops
4On our trips
Length
1 to 15 daysSmall groups
Best months
May to JunTrips run Apr to Oct
From
$249Per person

The Midwest: Illinois and Missouri

What the road is like in Illinois

Route 66 leaves Chicago on Adams Street, runs southwest through Cicero, Willowbrook and Joliet, then straightens out across the corn and soybean fields of central Illinois. For much of the way the old road runs beside I-55, sometimes on the frontage road, sometimes a field away, so you can drive the original concrete while trucks pass on the interstate. The towns come every 10 to 20 miles: Wilmington, Braidwood, Dwight, Odell, Pontiac, Bloomington, Lincoln, Springfield, Litchfield. Each kept something from the road years, a station, a diner, a mural on a brick wall. The state line is the Chain of Rocks Bridge over the Mississippi, about 300 miles from the start.

We cover Illinois on six trips. The End to End journey, the classic convertible and the motorcycle trip all start in Chicago with a welcome dinner and leave the next morning. The six day Illinois and Missouri trip takes it slower, with a night in Springfield and time in the Lincoln sites. Main Street Museums starts in Joliet and spends a full day between Pontiac and Springfield. For a single day, the Chicago to Pontiac classic car trip puts three guests in each restored 1950s or 1960s car, driven by members of a local car club. Darlene Moss, a former librarian from Pontiac, leads most of our Illinois days.

Route 66 trips through Illinois, 2026 and 2027

Per person sharing a double room. Trips that only cross part of Illinois are listed too.

All 16 trips

6 trips

    Your own private trip

    Car club, family reunion or friends: any trip can run just for your group on your dates, from 6 travelers.

    Private and group trips

    Deals and early booking

    Save $150 per person on 2027 departures booked by January 31, 2027, plus last-minute prices on November and December 2026 dates.

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    Not sure which stretch?

    Tell us how many days you have, the month and what you love: neon, diners, museums or open desert. A trip advisor in Tulsa suggests two or three trips.

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    4 stops

    Where our trips stop in Illinois

    Begin Historic Route 66 sign on a downtown Chicago street between glass towers

    Chicago and the Begin sign: Where the Mother Road begins

    Route 66 starts one block from Lake Michigan, at the brown Begin Historic Route 66 sign on Adams Street just west of Michigan Avenue. The highway was commissioned in 1926, and because Adams and Jackson are one-way streets, westbound travelers start on Adams and eastbound ones finish on Jackson. Our groups meet early, take the photo before the traffic builds, then walk to Lou Mitchell's on Jackson Boulevard, a diner open since 1923 that hands donut holes to the people waiting in line. The Art Institute of Chicago sits across the street from the sign if you arrive a day early. The classic car day trip meets at the sign at 8:00, and the multi-day trips leave from here the morning after the welcome dinner.

    • Photo at the Begin Route 66 sign on Adams Street
    • Breakfast at Lou Mitchell's, open since 1923
    • The Art Institute of Chicago across the street

    Best monthsApril to October

    Trips that stop here

    Gemini Giant astronaut statue holding a rocket beside Route 66 in Wilmington, Illinois

    Joliet and the Gemini Giant: A spaceman and a prison town

    Two of the best known sights on Illinois 66 sit about 20 miles apart. In Joliet, the limestone walls of the Old Joliet Prison, opened in 1858 and closed in 2002, still loom over Collins Street; the Blues Brothers made it famous in 1980, and guided tours now go inside. Downtown, the Rialto Square Theatre has stood on Chicago Street since 1926, the same year Route 66 was born. South in Wilmington stands the Gemini Giant, a fiberglass spaceman nearly 30 feet tall holding a rocket, put up in 1965 at the Launching Pad drive-in. Our road captain Ray Lindqvist grew up in Joliet and knows every alignment through town. On the way out of Chicago we stop at Dell Rhea's Chicken Basket in Willowbrook, a fried chicken stop on the road since the 1940s.

    • The Gemini Giant at the Launching Pad
    • Old Joliet Prison walls and gate
    • Fried chicken at Dell Rhea's Chicken Basket

    Best monthsApril to October

    Trips that stop here

    Swinging footbridge over the Vermilion River in a green park in Pontiac, Illinois

    Pontiac: Murals, swinging bridges, a road museum

    Pontiac showed small Illinois towns how to live off the old road again. The Illinois Route 66 Hall of Fame and Museum fills the old firehouse behind City Hall, and outside stand Bob Waldmire's Volkswagen van and the school bus he lived in, both covered in his drawings. Around the courthouse square, more than 20 outdoor murals cover brick walls, and three swinging footbridges cross the Vermilion River. Our road captain Darlene Moss was a librarian here for years, so the walk comes with names and stories. On the drive down we stop at the restored 1932 Standard Oil station in Odell and at Ambler's Texaco in Dwight, which pumped gas from 1933 to 1999. The classic car day trip has lunch in Pontiac before turning back to Chicago.

    • Illinois Route 66 Hall of Fame and Museum
    • Walk of the downtown murals and swinging bridges
    • Odell Standard Oil station and Ambler's Texaco

    Best monthsApril to October

    Trips that stop here

    Lincoln Home, a brown two-story house behind a white picket fence in Springfield, Illinois

    Springfield, Illinois: Lincoln's town and the Cozy Dog

    The Illinois capital was Abraham Lincoln's home for 24 years, and the Lincoln sites are the reason most of our trips sleep here. The Lincoln Home is shown by park rangers, the Abraham Lincoln Presidential Library and Museum opened in 2005, and his tomb stands in Oak Ridge Cemetery, where visitors rub the nose of the bronze bust for luck. Allow two hours for the museum. The Route 66 piece is the Cozy Dog Drive In on South Sixth Street, home of the corn dog on a stick that Ed Waldmire introduced in 1946. Order a horseshoe too, the local open sandwich buried in fries and cheese sauce. North of town, Funks Grove has sold maple sirup, spelled the old way, since the 1890s, and we stop when the shop is open.

    • Abraham Lincoln Presidential Library and Museum
    • A Cozy Dog on South Sixth Street
    • Maple sirup at Funks Grove

    Best monthsApril to October

    Trips that stop here

    Coach, convertible or motorcycle

    Ways to drive Route 66 in Illinois

    1. By small coach with a road captain

      On the End to End journey, Illinois and Missouri, and Main Street Museums, you ride in a 24-seat coach with no more than 14 guests, so everyone has a window. A professional driver handles Chicago traffic while Darlene Moss or Ray Lindqvist talks you through the towns. We leave I-55 at every exit worth taking: Odell, Dwight, Pontiac, Atlanta and its Paul Bunyon giant, then a night in Springfield.

    2. In a classic car, with or without the wheel

      The Chicago to Pontiac day trip puts three guests in each restored 1950s or 1960s car, driven by members of a Chicago-area classic car club who know their engines and their stories. On Route 66 in a Classic Convertible you drive yourself: two guests share each restored 1960s convertible, and a mechanic follows in a chase truck with the luggage. Illinois is the gentle start, flat, straight and quiet.

    3. By motorcycle across the prairie

      Route 66 by Motorcycle starts at the Begin sign, with riders on rented Harley-Davidson touring bikes and a support van behind them carrying the bags. Illinois makes a good first day on a new bike: wide farm roads, little traffic, and stops every hour at a station, a giant or a diner. Hank Delgado leads the group, and the van can take a tired passenger for a stretch.

    One price

    What is included on our Illinois trips

    In Illinois our multi-day prices cover hotel nights in Chicago and Springfield (or similar), breakfast every day, the welcome dinner in Chicago, the road captain and professional driver or the convertible and chase truck, parking, and the museum entries named in each itinerary, such as the Lincoln Presidential Library and Museum. The Chicago classic car day trip covers the car and its club driver, lunch in Pontiac and the drive back downtown.

    Flights are optional: each trip page shows the add-on price for flying into the start and home from the end, from 10 US cities. Full list and payments.

    Included on every Illinois trip

    • Restored vintage motels and good 3 to 4 star hotels, double room with private bathroom
    • Breakfast daily plus the lunches and dinners listed in the itinerary
    • A road captain from the first day to the last, and local guides at museums and parks
    • Small coach with a professional driver, or your classic convertible or motorcycle on themed trips
    • Museum, park and attraction entries listed in the itinerary
    • Airport pickup on day 1 and drop-off on the last day

    Seasons

    Best time to drive Route 66 in Illinois

    Illinois has four real seasons, and we run here from April to October. April can still bring a cold rain, while May and June are green, mild and long, with daylight past 8:00 pm. July and August are humid, often 85 to 90 degrees, with afternoon thunderstorms that pass in an hour; the classic car day trip still runs then. September and October are our favorite months: dry air, harvest in the fields and cool evenings in Springfield. From November to March snow and short days rule out the trips.

    1. JanNo trips: No trips
    2. FebNo trips: No trips
    3. MarNo trips: No trips
    4. AprGood: Good
    5. MayBest: Best
    6. JunBest: Best
    7. JulGood: Good
    8. AugGood: Good
    9. SepBest: Best
    10. OctBest: Best
    11. NovNo trips: No trips
    12. DecNo trips: No trips

    Best monthsGood, some trips runNo trips

    Practical

    Route 66 in Illinois at a glance

    • Route 66 miles

      About 300 miles from Adams Street in Chicago to the Chain of Rocks Bridge, mostly beside I-55 through Joliet, Pontiac, Bloomington and Springfield

    • Main towns on the road

      Chicago, Joliet, Wilmington, Dwight, Odell, Pontiac, Bloomington, Atlanta, Lincoln, Springfield, Litchfield

    • Airports

      Chicago O'Hare (ORD) and Midway (MDW) at the start; Springfield (SPI) in the middle; St. Louis (STL) just over the river

    • Time zone

      Central Time, with daylight saving time from March to November

    • Road weather

      Spring is cool and showery, summer hot and humid with short storms, fall dry and mild; winter brings snow and ice

    • 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

    • Best months for our trips

      May, June, September and October; day trips also run in July and August

    6 questions

    Route 66 in Illinois: questions

    Where exactly does Route 66 start in Chicago?

    The Begin Historic Route 66 sign stands on Adams Street just west of Michigan Avenue, across from the Art Institute. Adams is one-way westbound, so that is where trips heading for California start. The End sign for eastbound travelers is a block south on Jackson Boulevard. In 1926 the road began a block away at Jackson Boulevard and Michigan Avenue, but the Adams Street sign is where everyone takes the photo.

    How much of the original road can you still drive in Illinois?

    Most of it. The old road survives as frontage roads beside I-55, as Main Streets and as county roads, and a few short pieces of 1920s concrete are closed to cars and can only be walked. Our road captains choose the oldest drivable alignment where it makes sense and rejoin the interstate only where the old road is gone.

    I do not want to drive. Is the classic car day trip for me?

    Yes. On the Chicago to Pontiac day trip you ride as a passenger, three guests per car, and members of a classic car club do the driving. The trip meets at the Begin sign at 8:00 and is back downtown about 18:30. It costs $249 per person and is paid in full at booking.

    Can I do just Illinois and Missouri?

    Our Illinois and Missouri trip runs six days from Chicago to Springfield, Missouri, with time for Lincoln's Springfield, St. Louis and the Ozark motel towns. It is our most relaxed section trip and costs from $2,190 per person. We can book flights into O'Hare and home from Springfield-Branson National Airport.

    How do I get from O'Hare to the start hotel?

    The CTA Blue Line runs from O'Hare to the Loop in about 45 minutes and costs a few dollars; a taxi or rideshare takes 30 to 60 minutes depending on traffic. Our multi-day trips start at the hotel on day 1, with the welcome dinner that evening, so a flight that lands by mid afternoon is enough.

    Which Illinois towns are worth an extra night?

    Chicago, for its architecture boat tours and museums, and Springfield, for the Lincoln sites, which deserve a full day. Our trip advisors can add hotel nights before the start in Chicago at the same hotel the group uses.

    Next on the road

    Keep driving from Illinois

    The whole route
    Brick row of rooms and the tall sign of the Munger Moss Motel, Lebanon, MissouriRoute 66 in Missouri5 trips, from $2,190 Pale yellow trusses of the Pony Bridge repeating over the Canadian River in OklahomaRoute 66 in Oklahoma7 trips, from $179

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    Drive Illinois on the old road

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