Most Route 66 travelers leave Chicago too fast.
They land at O'Hare, snap a photo of the "Begin Route 66" sign, and gun it for St. Louis before they've even processed where they are. Big mistake. Chicago isn't a starting line — it's the first city on the road, and it deserves a full day before you head west.
Here's how to do it right.
The "Begin Route 66" Sign
The official starting point of Route 66 is the corner of Adams Street and Michigan Avenue, right in front of the Art Institute. The sign itself is small, brown, and easy to walk past — but it's the most-photographed lamppost on the Mother Road, and the photo is non-negotiable. Stand in front of it, get someone to take the shot, and you've officially started the trip.
A note: there are actually two signs. The "Begin" sign on Adams (one-way westbound) and an "End Route 66" sign on Jackson Boulevard, one block south (one-way eastbound). The Adams sign is the real starting line. The Jackson one is for travelers finishing their eastbound trip.
Lou Mitchell's — Breakfast First, Always
Before you point the car west, eat breakfast at Lou Mitchell's. The diner has been on Jackson Boulevard since 1923 — three years before Route 66 was even commissioned — and it's been feeding road trippers ever since. The menu is unfussy classics: thick-cut bacon, fluffy omelets in a skillet, hash browns, and homemade Greek toast (think buttery, slightly sweet). Every woman who walks in gets a free box of Milk Duds at the door. It's that kind of place.
Get there early — the line on weekends can stretch around the block by 9am, and they don't take reservations.
What to See Before You Drive
If you've got a full day in Chicago before you leave, here's the short list:
The Art Institute of Chicago. Right next to the starting sign. American Gothic, Nighthawks, a Sunday Afternoon on the Island of La Grande Jatte — you can see the most famous paintings in America in two hours. Worth the detour even if museums aren't normally your thing.
Millennium Park. The bean (officially "Cloud Gate") is one block from the sign. Take the photo, walk the park, and grab a coffee at the Modern Wing café.
Chicago Architecture River Cruise. If you have 90 minutes, this is the best way to understand the city you're about to leave. The boats run from May to November.
Pizza. You can't leave Chicago without eating deep dish. Lou Malnati's (the original, on State Street) or Pequod's (better, in our opinion, with its caramelized cheese crust). Skip Giordano's — the tourists' choice isn't the locals' choice.
Where to Sleep Before You Go
If you can swing it, stay in the Loop or River North so you can walk to the starting sign in the morning. The Palmer House Hilton is the most historic — it opened in 1871, claims to have invented the brownie, and was a Route 66 traveler favorite back in the era of cross-country car trips. It's not cheap, but it's a memorable first night.
Cheaper alternative: the Freehand Chicago in River North is a great hostel-meets-boutique-hotel hybrid with a famous bar (The Broken Shaker) downstairs.
Practical Tips for Day One
Leave Chicago in the morning, not the afternoon. Chicago traffic is brutal in any direction from 3pm onward. Aim to roll west by 10am — that gets you to St. Louis (about 300 miles, ~5 hours via the modern route, longer if you follow original 66) by dinner.
Don't try to follow original Route 66 out of Chicago. The original alignment through the city is now a tangle of one-way streets, construction, and dead-ends. Drive south on I-55 (which roughly parallels the old route) until you're past the suburbs, then pick up old Route 66 alignments through small Illinois towns like Joliet, Wilmington, and Pontiac.
Cash for the diner. Lou Mitchell's takes cards but the tip is better in cash.
Don't skip Pontiac. About 100 miles southwest of Chicago, the Illinois Route 66 Hall of Fame and Museum is in Pontiac and it's a perfect first roadside stop. Free, well-curated, and you'll get a better sense of what's ahead.
Back to the Pillar
Chicago is stop one of ten. The full route to Santa Monica is laid out here: Most People Drive Route 66 Wrong. These Are the 10 Stops That Matter.
Next stop: St. Louis, where the Gateway Arch marks the unofficial start of the American West.
