Chicago, Illinois
The start sign, the lakefront and the breakfast that kicks off 2,448 miles.
Chicago is where the Mother Road begins — the sign on Adams Street, the lakefront, and Lou Mitchell's donut holes. You'll pick up the bike, point it west, and the whole adventure unrolls ahead of you. Spend a morning here before you roll.
History
Route 66 was designated in 1926, starting at the intersection of Michigan Avenue and Jackson Boulevard — the official start sign now sits on Adams Street. Chicago was already America's rail hub and the logical eastern terminus: every westward journey, from the railroads to the Mother Road, began at the shore of Lake Michigan.
Why Visit
It's the start line. Grab breakfast at Lou Mitchell's, find the Route 66 start sign, take the photo, and head out. A few hours here is all most riders need before the road calls.
Best Motorcycle Roads
Lake Shore Drive (out of town)
Roll south along Lake Michigan before cutting west — the city skyline at your shoulder as the open road opens up.
Old Route 66 — Chicago to Wilmington
The first real stretch of the Mother Road, straight through the southwest suburbs toward the Gemini Giant.
Best Hotels
The Wheeler Mansion
Mid-rangeA restored 1870s mansion near the start sign — characterful and quiet before an early departure.
Hampton Inn Downtown
Mid-rangeReliable, central and walkable to the start sign and Lou Mitchell's. Secure parking for the bike.
Best Restaurants
Lou Mitchell's
Diner
The original Chicago breakfast institution feeding Route 66 riders since 1923 — donut holes on the way in.
Must Try · Donut holes and a Greek omelette
Portillo's
Chicago
Italian beef and Chicago dogs — the city in two sandwiches before you leave.
Must Try · Italian beef, dipped
Hidden Gems
- The Route 66 Start Sign on Adams Street — the official photo, take it before you ride.
- The lakefront bike path for a final look back at the skyline.
- Union Station — the rail terminus that made Chicago the start of every westward journey.
Photography Spots
- The Route 66 Start Sign on Adams Street, bike beside it.
- The Chicago skyline from Lake Shore Drive as you head south.
- Lou Mitchell's neon sign at breakfast.
Sunrise & Sunset
Around 5:30am in summer. The lakefront at dawn is the city at its quietest and best.
Over the lake — catch it from the lakefront path before dinner.
Practical Information
- Shell on Roosevelt Road — handy as you head west out of the city.
- BP on Ogden Avenue, the old Route 66 alignment.
Street metered parking is plentiful downtown. Most hotels offer valet. Park at the start sign for the photo, then move on.
Suggested Walking Routes
Start Sign to the Lake
A flat 1-mile walk from the Adams Street start sign to the lakefront — the official beginning and a great last look at the city.
Loop architecture stroll
A 30-minute wander through the historic Loop before you pick up the bike.
Weather & Ride Difficulty
Humid continental — hot, humid summers (30°C+), crisp springs and autumns. Rain can roll in off the lake fast. Check the forecast before you leave.
Urban departure needs care, but the roads out are straight and easy. The only challenge is Chicago traffic — leave early if you can.
Nearby Attractions
- Route 66 Start Sign (Adams Street)
- Lou Mitchell's
- Lake Michigan lakefront
- Union Station
Frequently Asked Questions
The official start sign is on Adams Street, just west of Michigan Avenue, in front of the Art Institute. That's the photo every rider wants before pointing west.
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