My fiancé and I are pondering a move to the Midwest to be closer to our respective families (fairly evenly distributed across the entire region). Chicago seems an obvious choice, but I've hated every trip I've ever taken there. Where are the good parts? Please show me it's not full of suck.
We both originally come from Midwestern college towns, and while we love our current home in a big East Coast city, we're looking forward to returning to our roots before we start to build a family together. On paper, Chicago sounds like a good option—lots of jobs, fairly central, easy access to a major airport, decent public transportation. In reality, though, the idea of moving there makes my skin crawl, probably because my experiences there have consisted of work events in the Loop, driving through the horrible gridded streets and one-story cookie cutter houses that make up the neighborhoods around O'Hare, wandering around Navy Pier as a teenager, and volunteering in Englewood in the late 90s where (rightly or wrongly) I was told not to go out after dark. In other words: awful.
On top of this, Chicago in general feels incredibly spread out and hard to navigate, and I have no idea where to find a concentration of the things that make us happy: good food (defined as great Mexican/Indian/Ethiopian/Thai rather than, say, Girl & the Goat), unpretentious but local coffee shops, bars with huge beer lists, weird little stores that sell books or odd ceramics or cocktail tools & supplies, storytelling hours, a non-Lululemon-filled yoga studio, fairly easy (less than 2.5 hours) access to great hiking/camping/kayaking/rafting, old houses (rather than giant apartment buildings) to live in, a walkable (less than 30 minutes) commute, great trails/places to go on long runs. I know these things all exist in Chicago, but when I've looked for recommendations before, it seems like everything awesome is at least 45 minutes by train away from every other awesome thing.
Right now, Milwaukee, Madison, Ann Arbor, or even Iowa City all seem like better choices—smaller, more walkable, more navigable, far easier to identify where we'd actually want to live. That said, we keep coming back to Chicago for job and location reasons. What can you tell me that will help me understand why people love this city? I'm specifically interested in:
- Specific neighborhoods we should consider, based on the preferences above
- Awesome hiking/camping/kayaking/rafting/etc. within a 2.5 hour drive of the city (we live within that distance of the ocean, mountains, dozens of campgrounds, and multiple forests right now, and by comparison Chicago feels pretty...boring)
- Links to resources that will help me get a better feel for individual parts of the city, rather than just "Chicago is awesome check out the bean"
(Conversely, if you've considered Chicago but chosen one of the other cities I mentioned, I'd welcome insight into what ultimately tipped your hand.)