If you're planning to drive Route 66, Chicago is your launchpad — or your grand finale, depending on which direction you're headed. Either way, this isn’t just a beginning or an end. It’s a moment. A place where something stirs inside you. A city that’s vibrant, bold, and packed with that electric energy you want at the edge of an adventure.
When we stood under the “Begin Route 66” sign, right there at the corner of East Adams Street and South Michigan Avenue, we looked at each other and smiled.
This was it. The real adventure was about to start.
We had already come a long way — a real coast-to-coast experience. We flew into New York (a city we already knew and loved), then took a Greyhound bus all the way to Buffalo — a true taste of the American bus life that we’ll never forget 😅 — just to visit the stunning Niagara Falls. Standing there in front of those thunderous, majestic waters was already a powerful beginning. But standing in front of that humble brown-and-white Route 66 sign in Chicago… that was when the journey really took shape.
It hit us: we were about to cross the entire country, from this exact sidewalk to the Pacific Ocean.
Where Route 66 Actually Starts and the Story Comes Alive
One fun detail for fellow road lovers: Chicago doesn’t just have one Route 66 sign — it has two. One marks the starting point on Adams Street, and just a block away on Jackson Boulevard, you’ll find the “End” sign. Yes, you should visit both. On foot.
Begin and end sign in Chicago
- Starting Point: East Adams Street at South Michigan Avenue
- Ending Point: East Jackson Boulevard at South Michigan Avenue
They’re just one block apart, and yes, you should visit both. Walk it — don’t even think about doing it by car; on foot, you can really soak it in, snap your photos...
It’s the perfect contrast to the wide, open road that lies ahead.
We took our time. Snapped the usual photos, of course. But we also stood quietly for a moment, letting it all sink in. We felt that little thrill knowing we were about to follow a road that stretches over 2,400 miles across eight states — a road where thousands of travelers, dreamers, couples, and explorers had begun their Route 66 journeys for nearly a century. And now, we were part of that story too.
Breakfast with History: Lou Mitchell’s
No proper Route 66 trip should start without a visit to Lou Mitchell’s, just steps from the starting sign.
We arrived hungry and full of anticipation. It was packed, as always, but once inside, we were surrounded by vintage charm — black-and-white photos on the walls, the smell of pancakes and coffee, and a buzzing energy that made you feel like you were part of something historic. The staff was warm and welcoming, handing out donut holes like old friends.
As we sat at the counter, I remember looking around and thinking about all the travelers who had been in that exact spot before us — and all those who would follow. It's more than just a meal. It's a ritual.
The Spirit of Route 66 in the Windy City
Chicago was a thriving metropolis even back in the heyday of Route 66 — the 1930s through the 60s — and you can still feel that spirit. This was the edge of the frontier, where gas tanks were filled, dreams were packed into suitcases, and the open road called out with promise.
Chicago isn’t just the start of Route 66 — it’s where the whole idea of the road was born. Back in 1926, when the Route was officially established, it made perfect sense to begin right here: a booming city full of ambition, steel, and railroads.
The Midwest was America's launching point — and Chicago was the beating heart of it. You can almost imagine it: travelers loading up their cars, heading west in search of sun, work, a new life. California wasn’t just a state — it was a dream. And Route 66 was the thread that connected that dream to the rest of the country.
Walking through certain museums or just looking at old black-and-white photos of those early days — diners lit by neon, gas stations with round glass pumps, dusty roads lined with Studebakers and Chevys — you can’t help but feel it. That sense of hope. Motion. Possibility.
Today, the road is mostly symbolic — but back then, it was freedom on four wheels.
If you close your eyes downtown, you can almost hear the buzz of neon signs, the hum of classic engines, and the clinking of diner plates. Some of those places are still around — or at least, their bones are.
Our Little Ritual: A Farewell and a Glimpse
Out of curiosity, we also went to see the “End” sign on Jackson Blvd — and it had its own kind of magic.
We hadn’t even started the trip yet, and somehow, we were already thinking about doing it in reverse one day. That’s the beauty of Route 66. Even before you begin, you’re already dreaming about coming back.
Our Romantic Night on the Water
Chicago isn’t just the start of Route 66. It’s a destination in itself.
That evening, we took a lake cruise while the sky turned to gold. As the fireworks lit up the skyline and reflected across the lake, we just stood there, holding hands, watching the city sparkle. The silhouette of skyscrapers, the warm summer air, the colors dancing on the water — it was pure magic. One of the most romantic and cinematic moments of our entire trip.
What Not to Miss in Chicago (Before Hitting the Road)
There’s so much to see and do here, especially if you give yourself a full day or two before heading out west. Here are some of the highlights we loved — especially for Route 66 fans:
- Grant Park – A peaceful green space with amazing skyline views, perfect for decompressing before a long drive.
- Castle Car Wash – A funky turreted building along the old route on Ogden Avenue. Not active anymore, but a great photo stop.
- Former Mercury Oil Station – A vintage gem repurposed but still proudly displaying its classic character.
- Art Deco Midland Hotel / Hotel Chicago – A touch of old-school elegance and history.
- Henry’s Drive-In in Cicero – Technically just outside Chicago, but it deserves a mention.
We had just left the city when we spotted it. Couldn’t resist. Pulled over, ordered a hot dog and fries, and suddenly — boom, the trip had truly begun.
Sitting there on a red bench, food in hand, I remember saying:
“If we stop for food every time we see something cool… we might never leave Illinois or USA”
And honestly, we were totally okay with that.
Take a Day or Two — Chicago Deserves It
I know the excitement. You’ve just landed, picked up the car, and you’re itching to hit the road. But trust me — give Chicago a little time. It’s the perfect way to ease into the journey.
Spend a day (or even two) soaking it all in:
- Wander through Millennium Park, snap the classic photo at “The Bean” (Cloud Gate), and just enjoy the energy of the city around you.
- Don’t miss the Art Institute of Chicago — even if just for the impressionists or that dreamy Seurat painting you’ve seen in movies.
- Get a new perspective on the city with the Chicago Architecture River Cruise — we did it, and it was surprisingly fascinating (even for non-architecture nerds).
- Walk the Skydeck at Willis Tower and test your courage on the glass floor. The views are stunning on a clear day.
- Stroll the Navy Pier, especially at sunset. Even just watching the boats or grabbing a snack feels like a little vacation inside your big trip.
- Of course, try the deep-dish pizza 🍕 — it’s cheesy, over-the-top, and 100% necessary.
- If you’re into music, catch a live blues show before you go. There’s something magical about hearing the roots of Route 66 in a smoky Chicago bar.
🛣️ And if you’re up for a Route 66 treasure hunt, follow part of the original 1926 alignment through the West Loop and Ogden Avenue — it’s not fully marked, but you’ll find clues in old signs and buildings.
🎨Some murals and painted Route 66 logos are hidden around the West Side too — a little urban scavenger hunt for history lovers and Instagram seekers alike.
Oh — and one last tip:
🍩Grab a pastry to go from Lou Mitchell’s before you leave the city . Starting your journey with something sweet from a place that’s been feeding travelers since the early days?
Feels just right.
A Few Personal Tips Before You Start
- Parking downtown is pricey and often confusing. Park once and explore on foot or by transit — it’s the best way to feel the city.
- Buy your Route 66 guide/map here — local bookstores often carry great editions with unique insights.
- Spring and fall are the best seasons to start the trip from Chicago: less heat, fewer crowds, and perfect golden light for photos.
- Go early if you want great shots at the “Begin Route 66” sign or a quiet table at Lou Mitchell’s.
- Talk to locals — you’ll be surprised how many have Route 66 stories of their own, or know someone who’s done it.
Saying Goodbye (But Not Really)
Chicago gave us the perfect kickoff. It was intense, exciting, and full of energy. But even as we left, cruising slowly through the first suburban stretches of the Mother Road, we already knew this wasn’t just the beginning of a drive — it was the start of something bigger.
That feeling, that mix of curiosity, nostalgia, and pure wanderlust, would stay with us for every mile.
We kept talking about it for days after — the city, the vibe, the contrasts. From the towering skyline to the tiny diners. From the rush of Michigan Avenue to the peaceful streets leading west.
And just like we did in Santa Monica, when we touched the “End of the Trail” sign and felt that deep, emotional rush…
we promised ourselves we’d do it again. Maybe from west to east next time. Maybe differently. But absolutely, definitely, again.
Because once you’ve stood at the start of Route 66 in Chicago…
once you’ve felt that click in your heart when the journey begins…
you know you’ll never stop loving this road 🛣️✨.
A Personal Reflection
When I left Chicago, I didn’t know what to expect. I had a rough plan, a full tank, and a heart ready for whatever the road would throw at me. That first stretch, heading southwest out of the city, was magical. I was leaving behind skyscrapers and diving into the unknown — and that’s the real beauty of the Route.
Whether Chicago is your starting point or your journey’s end, treat it like a sacred moment. Because it is. This is Route 66. And you’re now part of its story.
