Thanks for this. I think the plan would be to take a year or two and rent someplace in the city even if it is more expensive so we can experience the city and get settled in before kid(s) arrive and force our hand. We have some friends moving back to Chicago after a couple years in Brooklyn that are settling in Morgan Park, actually so that's funny you bring it up. Our combined incomes - while nothing extravagant - should be enough to make the $2k/month rent work. And that is good to know about the area around campus as I have never actually ventured around there. In Boston I commuted from South Boston to Cambridge so I don't mind a bus or train ride, assuming it's mostly reliable (which wasn't always the case with the T in Boston).
Well, Morgan Park, Mt. Greenwood, and Beverly are all bunched together. And they're still considered Chicago. To me, they provide a bit of the "city feel" without the chaos of being in the city proper. Hybrid suburb/city neighborhood, basically. Quite a bit of green space and parks and such. Lots of bars and food places. The Western Crawl was a big hangout for us in our early 20's, and is basically just a big string of bars/taverns/pubs up and down Western Ave. between 103rd and 118th streets in Beverly. There's like 20+ places, I believe, in that short stretch. And I'd say the cost is quite a bit better than living in any of the nicer neighborhoods within the major parts of the city.
If you were dead set on somewhere in like the city "proper", with a $2k budget, you'd probably be able to find something around South Loop, Printers Row, Near South Side, and other neighborhoods around there. Just do your research on the neighborhoods. As you get further north and north of downtown, prices start to skyrocket a bit.
Any time I've used the trains in Chicago, they've been reliable, but I haven't used them for something like commuting every day. Only for going to events and such in the city. I have friends that used them every day, though, and I imagine they would say it's pretty reliable. Never heard many complaints from them.
And yeah, you don't want to venture too far off campus in the areas surrounding it, unless passing through in a car or whatnot. Anywhere east towards the lake would be fine, but I'd avoid doing too much adventuring south, west, or north of the campus. Then again, I probably haven't been over that way in 10 years, so... it may all be changed now.
We do have a couple guys who have lived, or still live in the city, but I think they were primarily north side. They may be able to offer a little more insight into costs and such up there.
@Kurtosis @x Tame Impala