Of course, the topography doesn’t help either. The city is built on the intersection of three rivers (if you didn’t know that, prepare to have Yinzers gasp in horror when you act surprised), so bridges are necessary to get you to the other sides. Picked the wrong bridge? Oh ho, you better tack on an extra 20 minutes to your commute! All the hills and rivers make for some dangerous roads, especially in the winter time.
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I lived in the eastern suburbs for years and I never understood why the parkway (the parkway refers to I-376, which is the main artery into the city) starts at 3 lanes each way and cuts down to 2 lanes later. Forget about HOV lanes: the ones that exist suck, which are few and far between. However, one cool little aspect is the concept of backroads and shortcuts. Houston didn’t have these and I don’t drive in Chicago, so I can’t really comment. Until you understand where you’re going and the best way to get there, prepare to constantly get lost and spend needless hours in traffic.