Hi Colleen,
I don't have a lot of time to write this morning, but I wanted to say that I empathize with you. We have a habit of getting ourselves into no-win situations. Yours definitely seems to be being stuck directly twixt a rock and a hard place. I'm particularly dismayed that a company wants to make sure you have, and presumably drive a car, especially in a big city like Chicago. I can *sort* of understand it, but it'd be nice if they offered some sort of compromise...
Obviously your husband has a much deeper connection to the city than you do. But I'd like to tell a little story by way of example first and then (hopefully) somewhat lucidly tell you what I'm trying to get at.
I live in Memphis now. Before that I lived in Washington State (in the mountains), and before that Pasadena, CA, and before that Washington State (Tacoma), and then Seattle before that. Each time I moved, it was because I was SICK of where I was and the weather, or the people or the job. I just got so fed up with the monotony. I'm not talking about 10 or 15 years at each place, either. I'm talking 2 years MAX, often less than that.
When I moved from Tacoma, it was the biggest change for me up until that point. I was just sick of the weather - my mood was always grouchy and I had a hard time doing anything with my free time, other than taking extended walks in the rain. I had a pretty mediocre job at the library there, and often felt very trapped. So I thought to myself, well, maybe my life could use a reboot. Just cut all ties (somewhat), and move to somewhere that's the exact opposite of Ta-coma. The opportunity came when my sister, who had lived in San Francisco, moved down to the LA area to accept a job at a small (very) family-owned firm. After some events which I cannot remember happened, her boss offered me a job doing the IT stuff at the company. I really couldn't refuse, so I packed all my belongings into the smallest uhaul I could (I'm pretty nomadic, so I don't have much stuff), and drove down the coastal Highway 101 on a soothing change-my-life bildungsroman-inspired trip where I could almost *sense* literally leaving the dark clouds of Tacoma for the sunny skies of LA.
I lived down there for two years. Within about 3 months of me getting there, the company in question crumbled (not my fault! ), and I had a very very depressing time looking for a new job. I sent out maybe two resumes in May, and the rest of the summer kept trying to keep cool (no A/C in the place) by lounging around and generally going through my savings. As luck would have it one of the places at which I had applied saw fit to interview me in August, and I eventually took the job.
Ok, none of that was relevant, so much, but it does provide the sort of backstory that's necessary to make my point. It's a pretty normal life, moving, finding new jobs, making friends, working, filling up your time, etc. And it didn't occur to me right away, after I got there, because was so busy with the odds-and-ends of simply surviving and getting the technical details out of the way, but I came to realize how much I HAAAATED living there. The weather was ALWAYS sunny, no rain, too hot. The freeways were congested, it was smoggy and gross, the people were rude, and generally it was just as bad as Tacoma, and Seattle.
It took me a while to realize that, but it was nothing compared to how long I had to take to face up to the uncomfortable truth that it clearly wasn't the PLACE but the person who was to blame. I had changed EVERYTHING, and I was still feeling the same. I was the only variable, and that was a VERY hard pill to swallow. I had cut myself down to a starting point over and over again, and wasn't getting anywhere because I hadn't actually fixed the problem, or even identified the right one.

Sorry that was so rambly, but I think you can see my point. Your husband is almost certainly on the right track, if you don't mind me saying, to some degree. I recommend a vacation if you can swing it, but I would ask you to consider whether the "change of pace" is really something that'd help you sort things out, or whether it's simply an (in comparison) easy-to-fix scapegoat. It's ok if it's the first, of course, I don't mean to imply that everyone who moves is running away from something they can't, but it's *certainly* worth the extra examination!

And finally (phew!) I think you probably can keep just a little good in your life. We tend to gloss over the little good for the blatant bad, so I urge you to also spend some time identifying these things, as little as they might be. It might not be much, but it's a start to greater goods, and it tends to hold off the feelings of hopelessness. As always, you have people who are concerned about you here, and you're "worth it" to me. Keep us posted.

*Hug!*, and thanks for indulging my storytelling