I do have a comment on traffic– it was full of long, tiresome waits. A place might only be 10 miles away but could take you 30+ minutes to get there. Definitely not Syracuse.

- very very affordable, however not as much work to be found as in nyc and sf.
- bike lanes *everywhere*, really a great feature.
- beautiful landscaping, the city takes pride in their appearance.
- the weather is too harsh and extreme for my liking. 3 weeks of negative 20 was enough to make me start making plans to move out. i like heat but my husband couldn’t stand the humidity.
- very homogeneous. having grown up in SF and moving to Chicago straight from NYC, I was used to a lot more diversity. the lack of it was a shock to me.
- travel even 50 miles outside of the city and experience a lot of people staring at you, if you are brown like me
- ugh. the accent.

I can understand not loving SF, especially for what you are paying to live here. My mortgage is $3k and I live in Mission Dolores, but we’re thinking about moving to Portland once we build up enough equity.

I’d recommend checking out the Chicago Reader for housing listings. You’ll get a better idea of what you can expect to pay for certain neighborhoods.
http://classifieds.chicagoreader.com/chicago/Results?subsection=oid%3A123

Chicago is one of the most bike-able cities. Tons of bike paths on streets and more planned for the future. The lake path is a lovely route. Like another commenter said the city is flat and makes biking easy.

As far as rent/buying, you can get pretty great deals here. I currently live on the north side of the city in Edgewater in a huge three bedroom and we pay $1200. We have space for my painting studio in what should be the living room, space for my husband’s music studio in a bedroom, a spare bedroom for guests, etc. etc. So you can get a lot for your money.

My husband and I are currently looking into buying a 2 bedroom condo. You can spend anywhere between under $200,000 to well over $300,000. It all depends on where you are looking and what type of place you want.

Neighborhoods you might want to consider: Logan Square, Lincoln Square, West Loop (lots of lofts there), Fulton Market (also lots of lofts there), Andersonville, Edgewater, Rogers Park. Bucktown and Wicker Park are great places to go to, but it is getting super gentrified, expensive and when I lived there I had a lot less space than I currently do.

Good luck with your decision!

I’ve lived here for 7 years. Public transit is pretty good despite its faults. The city is pretty bicycle-friendly (lake paths & bike lanes & plenty of place to lock yourself up). Anywhere else you need to go, I would suggest looking into zipcar.com or igocars.com, which are both car shares. I live pretty far away from target but I can just book one of these for an hour or two (or sometimes the whole day to go to ikea) & like magic I have a car (insurance & gas all included).

lovely museums (Museum of Contemporary Art, the Art Institute, The Field Museum, The Museum of Science & Industry, the Children’s Museum, Garfield Conservatory). i can’t really comment too much on the music or fashion scene, but from what I hear tell, it’s not too shabby.

There are several very lovely yarn shops throughout the city as well.

Depending on the area that you choose, your neighborhood will certainly dictate the price of your flat. Ukranian Village is super cheap but not really near any trains (plenty of buses though). Wicker Park is pretty trendy so it’s a bit more expensive. Lakeview (which is a gigantic neighborhood that’s really more a few different neighborhoods- wrigleyville (steer clear unless you’re very partial to fratish dude-bros) & boystown (gay town USA- I live here and it is soooo wonderful. Many things to do & see. Very little parking.)

Chicago has great shopping, great art, a ton of interesting events, great schools, several art/design schools, etc. Compared to other cities, it is indeed cheap – my large one bedroom apartment is $725 a month, which is pretty reasonable. Thrift shopping is really good here, and public transport exists (one can debate endlessly about whether it is “good” or “reliable”).

However, for me living here has been really challenging. I moved here for grad school from the west coast, and it has been one culture shock after another. The racial/ethnic segregations are really bothersome to me as are the huge economic and educational disparaties. Chicago is one of the most segregated cities in the US (second only to New Orleans, I think), and as someone who grew up in one of the most diverse cities in the US, this has been really hard and disappointing.

Chicago, as indicative of the midwest, is very conservative. It’s far more liberal than most places in the midwest, but still far more conservative than the west coast. Although it has gotten easier in recent years, being a vegetarian (esp. a poor vegetarian) is harder here than the west coast. Luckily, however, we have two trader joe’s here now.

I think the trick to Chicago is finding your niche early. Given your art proclivities, you might have an easier time of it than I have. Although shopping is good, fashion is really disappointing. People here dress very conservatively (and to my eyes, fairly sexily in ways I find a little disconcerting – like students showing up to class wearing halter tops that barely cover anything), and even though I’m not really all that “out there” in terms of my choices, I get a lot of stares. It’s also very very image concious in ways I find really uncomfortable. Luckily my neighborhood is diverse and I am more likely to see people who kind of look more like me (not exactly – but in terms of fashion risks and liberaness), and that helps.

And actually, I would recommend my neighborhood. Others have recommended the Bucktown/wicker park area – which is great, but a bit too spendy and getting to be too gentrified to me (esp. damen avenue). However, I recall reading once those neighborhoods have the highest concentration of artists anywhere in the US. I live in the next neighborhood over – logan square. It is a really diverse neighborhhood in terms of economics, and has a nice mix of hispanic families, polish families, poor college students, and artists. We have one of the best restaurants in the city (Lula cafe) and there is a nice little local designer clothing store (wolfbait) that I think you’d like. They offer classes on things like screenprinting and other stuff. We have a stitch ‘n’ bitch in the ‘hood, and really great food and thrift shopping. We also have a target – which is awesome (and walking distance from my place).

The job market here is tough right now – but it may be that way everywhere, I dunno. I guess I just wanted to say that although it is a big city – it is still a midwestern city, and that can be surprising. People here are not laid back (which maybe wouldn’t bother you as much being from NYC) and there is far more anger/yelling here than I’ve ever seen (this was the hugest shock upon moving here, and I still can’t deal with it). But, I think if you find your niche, you can be really happy here. There are lots of pockets of artists, liberals, hipsters, social do-gooders, feminists, etc.

On the flip, Chicago has a level of racial/ethnic tension that I haven’t seen in other major cities. But then again, you must know about that, living in the Bay area. Also, it is true, the weather has a way of weeding out the thin-blooded. If you can stand a New York winter, you probably could stand a Chicago winter.
Good luck, I know what it’s like to be in this situation. I hope you and Pete settle in a place that’s right for you both.