Stories
Lou Mitchell'sPhoto: David Brossard, CC BY-SA 2.0, via Wikimedia Commons
Driving tour · Chicago

Route 66 in Illinois: Chicago to the Chain of Rocks Bridge

From Chicago to the Mississippi, a century on

7 h 42 min9 stops299 mi

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Stop 1 is free, no sign-up. All 9 for $4.99, refunded within 7 days if it isn't for you.

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The 9 stops

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    Lou Mitchell's

    The Diner That Was Here First

    Free sample · 2:38
    0:002:38

    You're standing on West Jackson Boulevard in the Loop, a short walk from Union Station, outside Lou Mitchell's. Look up at the front of the building. Running the whole length of the upper facade is a neon sign, the original from 1949, and it makes a modest little promise: Serving the World's Best Coffee. Hold onto that sign. It's the last thing a lot of people saw before Chicago fell away behind them.

    Route 66 began a few blocks east of here, near the lake. Generations of travelers stopped at Lou Mitchell's for one more proper breakfast before the long drive southwest, and the diner earned a nickname it still wears: the first stop on the Mother Road.

    But here's the thing most people get backwards. Lou Mitchell's didn't open because of Route 66. It was already here. When the diner marked its hundredth birthday in 2023, Route 66 was still three years short of its own. The highway wasn't designated until November 11, 1926.

    And Route 66 wasn't really built so much as named. The planners wanted the whole route open fast, so they stitched it together mostly from roads that already existed. Illinois had paved nearly all of its stretch by 1924, under the old name Illinois Route 4. That made Illinois the first of the eight states to finish its share, while long stretches out west were still gravel and dirt. Even that road had an older life: the earliest route from Chicago to St. Louis followed a Native American trail, later a stagecoach road. So a diner already serving coffee in the Loop simply woke up one day on the edge of America's most famous highway.

    The road made the reputation. The novelist John Steinbeck called it the Mother Road in 1939, and drivers had a darker name for the narrow, dangerous Illinois stretch: Bloody 66. In 1949 the diner moved into the building you're looking at, neon and all. Then the interstates came, and Interstate 55 largely replaced the old road.

    When people set out to rescue what was left, they came back here. In May 2002, the nationwide Route 66 restoration program was launched at Lou Mitchell's, and in 2006 the diner joined the National Register of Historic Places.

    One more detail for the road. When the TV competition Top Chef came here, the challenge was twenty minutes at the egg station, which the staff call the hull. Some of the best cooks in the country, humbled by breakfast. Get some coffee, and look at that sign one more time before you go.

    When you're ready, drive southwest, mostly on I-55, about 38 miles to Old Joliet Prison, a limestone fortress that opened before the Civil War.

The whole drive

9 stories across Chicago

7 h 42 min · 9 stops · 299 mi

Starts at Lou Mitchell's and ends at Chain of Rocks Bridge.

  • Plays right here in your browser, or in the app
  • One purchase for your group, on up to 4 phones
  • Refunded within 7 days if it isn't for you

Plan your drive

    How long

    About 7 h 42 min for 299 mi with all 9 stories. Going inside the sites adds time.

    Start and finish

    Starts at Lou Mitchell's and ends at Chain of Rocks Bridge.

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    Questions people ask

    How long does it take to drive Route 66 through Illinois?

    This route is about 299 miles from Chicago to the Chain of Rocks Bridge and takes about 7 hours 42 minutes of driving with all nine stories. Many people split it over two days, with a night in Springfield.

    Where does Route 66 start in Chicago?

    At the "Begin Route 66" sign on Adams Street near Grant Park. This drive starts a few blocks west, at Lou Mitchell's diner on Jackson Boulevard near Union Station.

    Can you drive across the Chain of Rocks Bridge?

    No. The old Route 66 bridge over the Mississippi is open to people on foot and on bikes only. It's known for the 22-degree bend in the middle.

    What stops are on the tour?

    The nine stops, in order, are Lou Mitchell's, Old Joliet Prison, Gemini Giant, Ambler's Texaco Gas Station, Odell Standard Oil Station, Funks Grove, Cozy Dog Drive In, Ariston Cafe and Chain of Rocks Bridge.

    Do I need the app?

    No. After you unlock, the tour plays right here in your browser: keep the screen on and tap each stop. The free Stories app adds GPS auto-play, so each story starts by itself when you arrive, with your phone in your pocket, and works offline.

    How many people can listen?

    One purchase covers your group on up to 4 phones. Share the link from your receipt, or everyone can sign in to the app with the same email.

    Does it work offline?

    In the app, yes: download the tour on Wi-Fi before you go. In the browser you need a signal, which is fine on most routes; open the tour once before you leave.

    When can I start?

    Any time. Start whenever you like and drive at your own pace; the stories wait for you.

    Can I give this tour as a gift?

    Yes. Tap "Give it as a gift", type their email and a note, and pick the day it arrives (Christmas morning works). They open it in their phone's browser; you get the receipt.

    Can I get a refund?

    Yes. If the tour did not work for you, email support@getstories.app within 7 days and we will refund it.

    Who made this tour?

    Stories writes each tour from public sources, checks every claim against them, and narrates it with a synthetic voice. The sources are listed at the end of this page; if you spot a mistake, tell us at support@getstories.app.

    About this tour and its sources

    You're standing outside Lou Mitchell's, at 565 West Jackson Boulevard, a short walk from Union Station. Look at the sign, the windows, the people lining up for breakfast. The neon sign reading "Serving the World's Best Coffee" dates from 1949. This is a good place to start a long road, because travelers have long begun their journeys here. The diner earned the nickname "the first stop on the Mother Road."

    Route 66 was officially designated on November 11, 1926, and it ran from Chicago all the way to the Pacific. Today you'll follow it across Illinois, from this diner to the Chain of Rocks Bridge over the Mississippi River.

    A highway is only pavement, so what kept Route 66 alive? The answer, stop after stop, turns out to be people. A prison built by its own inmates. Gas station owners who stayed at the pumps for decades. A grove where one family still makes syrup. A family who bought a fiberglass astronaut, and a town that later brought him home. And a cafe that began in Carlinville and moved when the road did.

    A surprising amount of this tour involves food. Come hungry.

    Before you go anywhere, stay right here. Your first story is about this diner, where the nationwide Route 66 restoration program was launched in May 2002.

    Written from public sources, every claim checked against them, narrated by a synthetic voice. Last checked October 2026.

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