not to disappoint you, but...
I grew up in Northbrook and know the area well. It's a very different place--more expensive to be sure, perhaps only slightly more diverse, definitely more densely built--but no more urban than it was before....
It used to be that folks living in the city had it good with their reverse commute, the traffic was so much lighter... But now that so many businesses have relocated to the suburbs, there is no "reverse commute" anymore--traffic is bad in both directions during morning and evening rush hours, and it's pretty heavy on 90/94 and 290/294 all day.
Not to disappoint you further, but... I assume you have been working 9-5 for a while and know the "grind" of that--get up early, commute, work, commute, go home and eat and feed the fish or whatever, go to bed and do it again... As a participant in this system as well, I would suggest that because the greater part of your week is spent in the work cycle, you should live closer to work. That's where your time is spent. Weekends come and you can always go into the city. The Metra system has weekend passes to take you into the Loop at a cheap price, and from there you can take the L or buses pretty much anywhere, where the action is. The 22 Clark Street bus runs all the time, it seems, maybe less on weekends, but it goes wherever you would want to, I would guess. On weekends you can park for free at a Metra lot, ride the train into the Loop on the unlimited pass, do your city living, go wherever...Andersonville, Lincoln Square, Lincoln Park, Bucktown, Old Town, South Loop, West Loop, Hyde Park, whatever....any of these Chicago neighborhoods are great for people your age---but commuting from them will be long and painful....
And who really works 9-5 anymore, anyway? Overtime is expected.
Plus, Allstate is huge. Have you been there? Once you make it through the gate, with morning traffic, all the other employees showing up at the same time, you could easily spend 10 minutes just driving through the Allstate property and another 10 finding parking.
So I would suggest cutting it in the middle, living closer to the city, but not in the city---Evanston. Evanston is the home of Northwestern U, so you have lots of young people and shops and restaurants geared toward young people, but it's a fairly wealthy area with families and retirees as well, so all kinds of stuff there. It's fairly liberal, with the U there, compared with other suburbs in the area. It's right on the edge of Chicago, so you could be there fairly quickly. But it's relatively close to Northbrook. I suspect in morning rush, it would still take you 45 minutes, at least, to get to Northbrook from Evanston.
You could live in Chicago, but those rents are high, and the Metra commute won't really work for you, especially if your hours might go long. I would live closer to work, because that's where most of your time is spent, and howl all weekend in the city.
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