I grew up on a farm, learned how to drive when I was 13, used to drive professionally (both trucks and for a Driveaway company) and I never would have imagined a time when a car wasn’t part of my life, but after moving to Chicago, poof, gone, not missed ever. The money not spent on, as listed above, car payments, repairs, maintenance, fuel, insurance, city stickers, parking meters, etc., plus not having to deal with parking and other drivers more than makes up for the occasional ‘kinda-wish’ thoughts. The buses and trains get us nearly everywhere we want to go, and cabs are plentiful for those times when we just don’t want to deal with standing out in the cold wind. We haven’t needed to yet, but if we wanted to we could always rent a car or do the i-go/zipcar route.
Not having a car by choice is so freeing, I never could have imagined. I never want to have to live anywhere where I have to have a car again (which means, most of the country).
Plus, we love Chicago. We love our neighborhood (Albany Park, on the northwest side). We love the movies and music and museums that are available to us. We love the lakefront and the skyline. We love the Loop. We love the generally friendly and laid-back atmosphere.
Downs? I can’t think of anything substantial. It’s a bit more expensive than average, though not as expensive as New York or other east coast cities. You have to be careful and aware, but regarding crime, I personally have never felt unsafe, though of course it only takes once for that to change, but nothing’s happened yet, in two decades of living here. There are a lot of people but, except for mornings on the L heading to the loop, and big events that attract hundreds of thousands of people like the Taste of Chicago and July 3rd Fireworks, it doesn’t seem oppressive to me. I’ve found I’m a big-city girl, and would love to live in New York or London, but Chicago is a good compromise. It has just about everything those cities would have, much cheaper. And it’s a transportation hub, which makes getting to other cities cheaper.
If you’re a New Yorker, you’ll be right at home here. It’s not quite as fast-paced or crowded or expensive, and you’ll surely miss some NY-specific things, but you’ll like it here.