Chicago traffic is legendary for a reason — it consistently ranks among the worst in the United States. Since Route 66 begins (or ends) right in the heart of downtown, you'll need a strategy to navigate the city without losing hours to gridlock. Here's your battle plan.
1When to Drive
Avoid I-55, I-90, and the Dan Ryan Expressway during rush hours (7–9:30 AM and 3:30–7 PM on weekdays). Weekend mornings before 10 AM are the best time to start your Route 66 journey southbound. If arriving on a Friday, wait until Saturday morning to leave the city. The stretch from downtown Chicago to Joliet (40 miles) can take 45 minutes on a clear day or 2+ hours during rush hour.
2Parking Downtown
Street parking near the Route 66 Begin Sign (Adams & Michigan) is nearly impossible. Use the Millennium Park Garage ($35/day) or the Grant Park South Garage ($28/day) — both are within walking distance. SpotHero and ParkWhiz apps can save 30–40% on garage rates if you book ahead. If you're just grabbing a photo at the Begin Sign, use a rideshare instead of driving downtown.
3Navigating South Out of the City
The historic Route 66 alignment through Chicago follows Ogden Avenue southwest through Cicero, Berwyn, and Lyons. It's a fun urban cruise with diners and vintage signs, but adds 1–2 hours compared to taking I-55 directly. For your first time, take I-55 south to Joliet to escape the metro area, then switch to the old alignment. The original route through Chicago neighborhoods is better saved for a dedicated city day.
4Tolls & E-ZPass
The Illinois Tollway system surrounds Chicago. If you're arriving from the east or north, you'll hit tolls on I-90, I-294, or I-88. Get an I-PASS transponder (Illinois E-ZPass) — toll-by-plate costs 50% more. Route 66 south on I-55 is toll-free once you pass Joliet, so the toll exposure is limited to the Chicago metro area. Budget $5–15 for tolls depending on your route in.
lightbulbPro Tips
Leave Chicago on a Saturday or Sunday morning before 9 AM — you'll be in Joliet in 45 minutes flat.
Take a photo at the Begin Sign the night before departure — it's beautifully lit and crowd-free after 9 PM.
The Ogden Avenue alignment through Cicero and Berwyn has great vintage neon signs — drive it as a loop, not your main exit route.
Waze is more accurate than Google Maps for real-time Chicago traffic — switch to it for your city navigation.