For the past three years, I've advised against traveling Chicago's grim four-mile (6.5 km) Ogden Avenue segment of Route 66. The recommendation was first made during a 2016 gun violence epidemic that frequently claimed RANDOM and INNOCENT victims.
The advice was based on FBI and Chicago Police data and a Chicago Tribune crime map. The zone bordering Ogden Avenue had the city's second-highest violent crime rate. While much of the gunfire was unpredictable, it tended to peak in summer, especially nights and weekends.
In 2017 and 2018 gun violence eased somewhat, but this remains a high crime area in a high crime city...even by American standards.
While the risk for 2019 is impossible to quantify, the reward is not. Ogden Avenue is desolate and lacking in Route 66 attractions. There's only a glorified gas station, known as the Castle Car Wash. (I have images on my site.)
Chicago's downtown Loop is well worth seeing, and relatively safe.
Then I'd recommend this simple detour: South on Lake Shore Drive to I-55 South (Stevenson Expressway). At Exit 286: North on Cicero Avenue, and West on Ogden.
You rejoin Rt 66, Ogden Avenue, in the safe suburb of Cicero IL.
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