I don't mean this post to be a competition; Chicago and Madison both have pros and cons. I just love comparing cities, and since I recently spent a bunch of time in Madison, these differences/similarities are fresh. As far as city comparisons go, this one's fairly weak. I'm not going to get into the sports, food, music, politics, or any interesting stuff of either city. I just want to write about the streets and the biking. FYI, I didn't research any of these; I'm post-workout blog vomiting.
Okay, if this were a competition, Chicago is the winner hands down just by virtue of The Grid. Directions and maps don't confuse me; I'm actually a great navigator. Madison, though, always gets me turned around. I wonder if living in Chicago has spoiled me; maybe The Grid is a crutch of sorts. Or maybe I just haven't spent enough time in Madison. Either way, I love hearing an address and knowing almost exactly how to get there without googling it. Madison (and most of Wisconsin) operates on the some streets straight, some not so much system. It's super easy to get lost and you most likely need directions to get anywhere, unless you are already familiar with the area.
Chicago is a huge bike city. Some neighborhoods more than others, but overall, biking in the city is a normal, popular thing to do. And yet, there are still very few protected bike lanes. In some areas, there aren't bike lanes at all, just the several feet between parked cars and traffic for bikes to maneuver through. A biker in Chicago needs to be super aware of his/her surroundings. Luckily, most drivers are also aware of their surroundings, even if they hate bikers. Madison also appears to be a bike city, and besides confusing streets has bike trails. Partially I'm guessing it's a college student thing, though I know Madison usually ranks as a healthy city. Still, I did see a lot of way protected bike lanes--like literally a separate area of the road just for bikes. So that's awesome for Madison bikers. Streets are confusing, but you can pay more attention to where you're going since you don't have to worry as much about being in traffic.
There you have it, for anyone wondering just how Madison and Chicago compare on two minor city details that actually come into play a lot in my own personal life, these are things I observed. I hope I've been super helpful.