Kinda? Chicago just doesn't feel very "Midwestern" to me, but I did grow up in Sioux Falls, which is definitely the Midwest.
Chicago is on the eastern edge of what I'd consider the Midwest, but it's not really any further east than Milwaukee, which is definitely Midwestern. I'm not sure if the dissonance is just due to Chicago being a World City, if that cosmopolitan vibe is interfering with a Midwestern baseline or vice-versa.
Michigan is soundly Midwestern lol you definitely cannot call Ohio and Michigan part of the East Coast, and both of those are East of Chicago. Chicago is in the heart of the Midwest.
Not East Coast but certainly Rust Belt or Great Lakes region. Nothing in Eastern Time is in the Midwest. It's the East. That's why they called it "Eastern Time".
We’ll have to disagree here. Part of Michigan is in CST, and living here my entire life everyone knows we’re Midwestern. Weird way for a Chicagoan to try to distance themselves from us when we’re next door neighbors.