Chicago: convince me it's awesome
January 15, 2014 8:22 PM   Subscribe

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.)
posted by anonymous to Travel & Transportation (40 answers total) 16 users marked this as a favorite
We chose Madison, not over Chicago, but over another Midwestern Chicago-sized city (Toronto.) Madison is very strong on what you call "things that make us happy" (and the hiking is a lot less than 2.5 hours away.) It is weak, obviously, on the things you list as Chicago's "on paper" attractions. But I'll say this: our airport is small, but it has direct flights to all the hubs and you can get there in 15 minutes from anywhere in town. Our public transport is just a fleet of buses, but there's no need for a subway here because you can get almost anywhere you need to go on your bike. It's butt-cold, but so is Chicago.
posted by escabeche at 8:57 PM on January 15, 2014 [1 favorite]

Unfortunately, despite the fact that you've been exposed to a lot of the worst of Chicago (Navy Pier, area around O'Hare), I think your perceptions are largely correct. Also, the dispersed nature of the city is something that you tend to feel everywhere and becomes a major aspect of your life here.

That said, you may like Andersonville. The "ethnic food" restaurants there are not great, but it's very close to the Ethiopian places in Edgewater which are very good. It has the Hopleaf (huge beer list), and some nice restaurants of the slightly pricier yuppie variety. Kopi coffee shop is cool, and Metropolis is nearby. I do think the people who frequent the yoga studio there (Yoga Tree) are somewhat close to the Lululemon type, however. There's a Swedish Bakery and some knick knacky shops (though I think it is a neighborhood that is getting more and more fru fru and that is reflected in new businesses that open there). It's also a very short drive up to Devon which has lots of Indian restaurants and shops. Also close to east Rogers Park which is somewhat sparse but also has some cool places. Andersonville also has a real DVD rental store which I love, and some small houses (rather than just buildings). It's a small neighborhood but one you may want to consider if moving here.
posted by Blitz at 9:05 PM on January 15, 2014 [5 favorites]

Most of what you want will be on the north side of the city but it sounds like you don't want to be in the city itself. If Andersonville doesnt fit your bill, try Evanston. It also happens to be a midwest college town.
posted by JoeZydeco at 9:06 PM on January 15, 2014 [3 favorites]

Yeah - you've seen the worst that Chicago has to offer, but I don't have it in me to talk you out of it. Because I finally moved to Seattle to at least have cool outdoors places to go, even if I do still have to spend far too much time in my car. The things you want are all there in the city, but they're not necessarily the least bit convenient to each other.
posted by wotsac at 9:16 PM on January 15, 2014 [1 favorite]

I agree with JoeZydeco. Evanston is great. Also, it's directly above East Rogers Park, Edgewater and Andersonville so you can be still pretty close to those neighborhoods too. It's very walkable and right by the lake. There are still a few used book shops. Some of the restaurants are kind of sterile (Chipotle and similar) and there are almost no mom and poppy "ethnic" restaurants, but there are cool places with character nonetheless. They have some nice coffee shops too.
posted by Blitz at 9:20 PM on January 15, 2014

What can you tell me that will help me understand why people love this city?

This is difficult because actually I kind of hate this city? But it's also home and I hate every other city MORE, so far...

If your idea of stuff to do is live music, small businesses, weirdos, artisanal cocktails, passive-aggressive urban biking, aggressive-aggressive pizza, political corruption as local circus, record stores, abandoned-lot gardening, encased meats, outsider art, watching the downfall of journalism, lake, Indian food, dibs, fucking-goddamn-it's-negative-40-let's-drink, pub quiz, live readings, independent radio, or tacos, COME ON DOWN, man, this is how we do.

If your idea of stuff to do is "be in nature," though... then yeah, it's hella boring. :( There is not really any nature nearby, though I guess you could be somewhere in 2.5 hours maybe? That might get you to, like, Wisconsin? Or maybe out near Rockford/Oregon? I've never looked, honestly; the very idea of hiking gives me psychosomatic tick bites.

It's true, everything in Chicago is 40 minutes from everywhere else. It's best not to think of it as a city but as a constellation of small towns. This is part of why people who love it, love it--neighborhoods have strong identities and characters because they form independently of each other. And because it gives the giant city a more human scale in actual practice. So really what you would have to do here is pick your small town.

Along those lines, Lincoln Square/Ravenswood will give you these:

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 . . . old houses (rather than giant apartment buildings) to live in

Especially Thai, especially beer, especially coffee. Seriously, I can give you actual names of the places to get each one of these things, and they are all within the area bounded by Ashland Ave/Western Ave/Irving Park Rd/Foster Ave.

River North/Streeterville/Printers' Row will give you this:
a walkable (less than 30 minutes) commute

(Assuming the commute is to the Loop, and must be 100% walk, not walk-to-train).
posted by like_a_friend at 9:54 PM on January 15, 2014 [7 favorites]

I love Chicago, but I've never lived there, just visited. I have several friends with families that are happy there, and I agree that Andersonville or Evanston are probably your best bets.

Is Denver midwest enough? It's worth consideration based on your requirements above.
posted by fyrebelley at 10:12 PM on January 15, 2014

You definitely have experienced the worst of Chicago, and not the best. I agree that Andersonville and Evanston would probably appeal to you. People I know who are there are very happy. Ditto Oak Park.

I lived in Chicago for over a decade and loved it. I lived in Hyde Park, Logan Square and the West Loop. Maybe not for you, but definitely not the horribleness you describe (which is there in other places, for sure).

I loved Chicago, but eventually we did move for two reasons: bad weather, no nature to explore. Sorry, the beautiful lakefront ultimately does not count.
posted by beanie at 10:51 PM on January 15, 2014

What about going back to one of your college towns and making the trip to Chicago when you need the culture fix?

When I was at the IA writers' workshop Chicago was an oasis for me. I also roadtripped to Kansas City , St Louis, the twin cities, Milwaukee and the other Big 10 (at the time) towns on weekends.
posted by brujita at 10:54 PM on January 15, 2014

Previously .
posted by professor plum with a rope at 12:46 AM on January 16, 2014

Seconding what has been said above.

But adding that if you get used to the el and are ok with taking a cab occasionally, pretty much everything you want (except the outdoorsy stuff) is there and accessible- just not all in the same neighborhood. (I'd add Ravenswood, Logan Square and Lincoln Square to the list of places to look.)

Also- a specific yoga studio rec- Om on the Range. I'm not promising totally lululemon free (nothing really is) but they have some of the best teachers in the area while still having an accessible schedule.
posted by susiswimmer at 1:57 AM on January 16, 2014

good food (defined as great Mexican/Indian/Ethiopian/Thai rather than, say, Girl & the Goat)
Ethiopian: Ethiopian Diamond
Mexican: Anywhere in the vicinity of Pilsen or Little Village (I'm not big on Mexican, so I can't tell you the best options)
Indian: Seriously, Devon Avenue is a paradise. And they deliver to most of the North Side too.
Thai: There is a huge Thai community in Chicago. My girlfriend and I get Thai almost once a week. Most Thai places are around the Red Line especially near Edgewater but it's a popular enough cuisine that there are Thai places in most neighborhoods (at least on the North Side).
unpretentious but local coffee shops, bars with huge beer lists
Too many options to get into, but yes, we have those. A lot of them, depending on where you live. There are just too many things to specify unless I know where you're going to live. Chicago is a gigantic metropolis with a very diverse population. Based on your questions, I would guess you would be happiest living around Bucktown if you want to be in the city. If a city-ish suburb is more your thing, Oak Park and Evanston are also good choices – walkable towns with access to the CTA trains into the city proper.

Honestly, as a life-long Midwesterner, the notion of Iowa City or Madison being "walkable" is funny to me. The only city in the Midwest where you can easily get around with public transit or walking/biking alone is Chicago. (Milwakuee might come in at a distant second.)

Of course, it's not perfect. Winter sucks in Chicago, but you're going to have a rough time with winter anywhere in the Midwest. Why not locate somewhere with a vibrant theater scene and copious Thai food?

It sounds like you've only seen the extremes of how bad the city can be. Basing your opinion of all of Chicago on a visit to Englewood in the late '90s would be like dismissing NYC as an apocalyptic wasteland based on a visit to Harlem in the '70s. If you could, I would arrange a visit and spend some time hanging around the Blue Line neighborhoods and/or Oak Park/Evanston to see how you like them. And please don't visit until, like, April, unless you want to deal with the worst of winter. Chicago is at its best in May, IMO.

Also: the NYTimes did a 36 Hours piece on Chicago recently.
posted by deathpanels at 5:56 AM on January 16, 2014 [4 favorites]

Why are you talking yourself into Chicago? If you don't like it, you don't like it. But, I will say that being there for business is different than living there.

My suggestion is to travel there for a vacation. Take a week and really explore different areas. I understand from Chicagoians that it's a city of neighborhoods. While you may not like Lakeshore Drive or the Loop, you might enjoy a little neighborhood.

At the end of the day though, if the vibe of the place doesn't work for you, then don't settle there. Pick Milwaukee or Madison or Minneapolis.

Life is too short to pick a city to live in by it's airport. (Says the lady who lives in Atlanta.)
posted by Ruthless Bunny at 6:53 AM on January 16, 2014 [2 favorites]

Everything you mention above can be found in (just to pick one neighborhood) Lincoln Square except the nature walks. Book Cellar, Bloom Yoga, Julius Meinl, Aroy Thai, Tiny Lounge, Huttenbar (beer bars in this 'hood run German), Beans and Bagels, boutiques along Lincoln Ave all for the Googling. And the Old Town School of Folk Music for music and art experiences from ages 6mos-99 years. It's the best thing in the city, IMO.

Look into Metra for walkable/train commute ideas-- assuming you'll work in the Loop. Houses are of course plentiful but expensive-- if you're willing to live farther away from a "walkable", i.e. walk-train commute then it will be more affordable. Lots of people drive to and park near a Metra stop.

It's hard to get an idea of what living in a neighborhood will be like while staying in a hotel. Maybe do a couple AirBNB visits?

There is a lack of hiking type nature, yeah. That's the one thing I miss.
posted by travertina at 7:03 AM on January 16, 2014

I love Chicago.

Pilsen is a cheeper neighborhood, primarily hispanic. It is close to Chinatown which for me is a huge bonus. It has an art scene and some nice coffee shops. However, the apartments aren't in the best shape and depending on your confort with crime it can make you feel a little queezy. I am a small white female, and I don't feel unsafe in my area at all. But I'm not you, so YMMV.

There is hiking (Palesadies, Wisconson Dells) but they are more in the 3-5 hour range of travel than the 2.5 hour range. There are parks, and some camping, but camping is expensive around the chicagoland area. Its best to drive out a little further. The furthur away from the city, the better the qualtity.

For some of the unique things: they are here! I promise! Its just finding them, and picking a location that you like.

Public transportation is wonderful. As long as you don't live in an outskirt part of town, you can get anywhere in about an hour.

The nieghborhoods mentioned in above posts fit what you are looking for pretty well.
posted by AlexiaSky at 7:10 AM on January 16, 2014

As others have said, if you don't like Chicago, then don't live in Chicago!

You sound like a perfect candidate for MINNEAPOLIS, however:

--good food (defined as great Mexican/Indian/Ethiopian/Thai rather than, say, Girl & the Goat): Mpls is becoming known for its huge resurgence in great food.
--unpretentious but local coffee shops: Yep
--bars with huge beer lists: I don't drink, but a friend of mine is always on Facebook posting pics of bars with 100+ taps, though I don't know which bars they are, sorry
--weird little stores that sell books or odd ceramics or cocktail tools & supplies: Oh, of course, but probably more so in St. Paul
--storytelling hours: Of course. My wife and I had many early dates at places like this
--a non-Lululemon-filled yoga studio: Yep. Mpls people aren't as pretentious, so you will see women at yoga studios in plain tightish pants and baggy shirts, ha
--fairly easy (less than 2.5 hours) access to great hiking/camping/kayaking/rafting: We have amazing places in less than 25 minutes' drive, and some places in Mpls proper itself!
--old houses (rather than giant apartment buildings) to live in: I currently live in a house built in 1939, previously a house from 1890 or so, etc.....
--a walkable (less than 30 minutes) commute: Depends where you live. Most people I know CYCLE to work, and yes, year 'round.
--great trails/places to go on long runs: Well, Mpls has 100s of miles of trails just within the city, which connect to 600 miles (or is it 800 miles?) of trails within the county.

--Also, Mpls is known for its amazing music and theatre which some critics say rival or exceed the theatre in NYC.

Sorry I don't have specific links, but I don't have the time to go through even a start of everything.
posted by TinWhistle at 7:14 AM on January 16, 2014 [3 favorites]

Cook County (in which Chicago is located) actually has the most natural space of any major metro county in North America, primarily in the form of the Cook County Forest Preserve. It's mostly a little way out into the suburbs, but there's quite a lot of it, and you can take the Metra to right near some trailheads (although more of the system is accessible if you drive). There is hiking, bike trails, horse trails, kayaking, canoeing, cross-country skiing, orienteering, etc. (I am personally fond of the Skokie Lagoons because I grew up near there and I remember when it was basically a sludge pond of grossness and you couldn't even touch the water because it was so polluted and now it's a beautiful, natural oasis, where you can eat the fish, but it's not very big. You can kayak or canoe through them, or bike from the bottom of it up to the Botanic Gardens and have lunch and bike back, it's nice.)

Off the top of my head, also within 2 hours would be Indiana Dunes National Lakeshore and the East Race Waterway on the St. Joe River for kayaking (which is used in kayaking competitions, that's all I know about it), both of which are accessible by car (South Bend is 1.75 hours by car) or by the vomit comet. I do not actually know anything about kayaking but I know a LOT of people who do it, there are a lot of places to go around here.

Starved Rock State Park, about 90 minutes away, very nice hiking and camping, totally underused by Chicagoans. Goose Lake is right up by Chicago. Des Plaines Fish and Wildlife Area is big. Emequon is about 3 hours away, but it's really nice; it's a newish wetland preserve that the Sierra Club spent years buying up before turning it into a wildlife preserve.

(If you live in the City, the Lakeshore is super-popular for joggers, but even better is that the Lincoln Park Zoo is free and you can jog around or even through the zoo, which a lot of people like to do if you go at quiet hours -- the gates open 3 hours before the zoo itself, so not a lot of animals are necessarily out, but you can jog by the polar bear and wave, it's just something a little different.)

That's just a few off the top of my head, I'm not very outdoorsy.
posted by Eyebrows McGee at 7:58 AM on January 16, 2014 [8 favorites]

I've lived in Chicago for 20 years and I love it here. But if you don't want to move here, don't.

Check out Madison, WI; Minneapolis, MN; Ann Arbor, MI; Milwaukee, WI; Iowa City, IA.

Chicago is wonderful, but it isn't for everyone.
posted by bibliogrrl at 8:00 AM on January 16, 2014 [3 favorites]

I'd also like to address the nature issue here for a second. If you guys are conflating "nature" with mountains, rapids, vast forests, and backpacking trails, then no, Chicago has none of that. But not because we've paved over or plowed under everything. This is prairie country--we're at the gateway to the Great Plains. There haven't been mountains or rapids or significant amounts of forest here for millenia, if ever. We also don't have oceans, deserts, rainforests, or tundra in Chicago. Sorry.

What we do have is prairie, wetlands, dunes, and glacial morraines and the like, and as Eyebrows McGee mentioned, we've actually done a pretty good job of preserving this stuff. Maybe not in the city proper, but the collar counties are full of parks and preserves. I'd argue that you can see more biodiversity in an afternoon at a lot of these places than you can see hiking for days through the forest. But if you just want trees as far as the eye can see, then we've got nothing for you here.
posted by gueneverey at 8:38 AM on January 16, 2014 [7 favorites]

Man, I feel bad that you haven't experienced the AMAZING Mexican/Indian/Ethiopian/Thai that Chicago has to offer. Sounds like you went on a tour of all the worst parts.

But yes, if you don't want to move here, don't. Chicagoans are deeply proud of their city for good reason but as with any city, if you are not open to it, it will not open itself to you.
posted by Windigo at 8:42 AM on January 16, 2014 [5 favorites]

I've lived in Chicago most of my adult life (also lived in Austin, Tx, Wash DC, and Philadelphia, Pa as an adult) and my family has been here since before the Fire. I seriously doubt I could be enticed to live anywhere else. Your description of Chicago as "hard to navigate" with "everything awesome... at least 45 minutes by train away from every other awesome thing." is nothing remotely like my experience here as a wide-eyed child, as a poor college kid, as a temporary suburban squatter, or as well-settled professional. My commute is under 45 minutes if I use public transit (most of that time is waiting for the bus--if I use the bus tracker, I can shave 15 minutes off), under 30 if I bike. Just about 90 minutes if I stroll through the park to get home, which I sometimes do on glorious spring and fall days. I can easily get to world class opera, theatre and restaurants without ever being in a car. Everything I need [fn1] is a 10-15 minute walk from either my house (which was built in 1890 and has glorious old timey features and is 1/2 mile from the nearest "giant apartment building"--depending on how you define that term) or my office.

But your experience is that Chicago is hard to navigate and everything is far away and awful. Clearly, you don't like it here, so don't move here. Life is too short to spend somewhere you hate.

[fn1] Everything I need includes: groceries; the indie comedy pub quiz; great venues who get diverse bands; excellent restaurants; kayaking; shopping; doctors; dentists; emergency rooms; tradespeople like cobblers, tailors, tattoo artists/piercers; local coffee roaster; locally brewed beer; an expansive liquor store; the Lake which expands as far as the eye can see; the Zoo; sailboat rental; golfing; the beach; specialty cheese shop; open mic night; improv; local bike shop; library; playgrounds. This is within 1 mile of my house or office.

Expand the radius to include the 4-mile distance home to office, you get very high class restaurants and high-class shopping and excellent museums; the best karaoke bar in existence; lots of improv; weird bike shop/coffee shop hybrids; galleries; indie/art movie theatre; wine bars; Old Town School of Folk Music; writers' workshops; language institutes; community centers. Too much stuff to mention.
posted by crush-onastick at 8:43 AM on January 16, 2014 [14 favorites]

Yeah, you really have experienced the crummiest parts of Chicago, and as a result your perception of the city isn't completely accurate. Nthing taking a look at Lincoln Square/Ravenswood, Logan Square, and Andersonville. Yes, it will take you 45 minutes to get to work if you live in Lincoln Square and work in the Loop, but once you get home all sorts of great stuff is at your doorstep. And it's not like that commute is empty space: Chicago is dense, and there's stuff at every El stop. If you really want to figure out if the city's right for you, try visiting again and concentrate on one of the above-mentioned neighborhoods. Find an AirBnB place in the neighborhood, and if you have any friends in the city, ask them for recommendations.

I'd also add that Chicago may be enormous, but you probably will not be spending your time traveling all over every square foot of the city. It's perfectly possible to stay within a mile or two of your home without running out of things to do.

My one complaint about Chicago, however, is that it seemed really difficult to get away. I know there's all sorts of parks and gardens and preserves in Chicago, and of course that enormous lake, but for the most part it's very urban and very large. It wasn't a huge deal for me, and I am certain that if it were I would have found ways to satisfy my outsdoorsy longings. (On preview: gueneverey has an excellent point. I'm an East Coast native and I love dense forests, hills, and oceans. The prairie has its charms, but doesn't do it for me in the same way. But that's a common theme throughout the Midwest.)

Finally, I have to strongly agree with everyone who says that if you don't think you'd like it there, don't move there. It's nearly impossible for a place to grow on you if you arrive with serious misgivings.
posted by Metroid Baby at 8:52 AM on January 16, 2014 [3 favorites]

You should definitely look more into Milwaukee. It's big enough to have everything you'd expect in a major city, and I think you'd like it a lot more than Chicago. It hits all of your good things marks - close to nature, and kayaking right in the city, on the river or lake, bars - oh, the bars!, indie coffee shops, old houses to live in, etc. There are lots of good little ethnic restaurants and other interesting places. Milwaukee has distinct neighborhoods with their own character, but anywhere in the city doesn't feel too far from anywhere else. Public transportation is limited to busses, but you can get most anywhere on them, and the city is quite bikeable. I can't say much about the job market, and most likely a commute wouldn't be walkable, depending on where you live, but there are a lot of good things about living here. There is lots going on, even in winter, and TONS in the summer. There's much more cultural stuff than I think most people who don't know the city would assume, and there are a lot of vibrant local communities.

And it's only a 90 minute drive or train ride to Chicago.
posted by catatethebird at 9:19 AM on January 16, 2014 [2 favorites]

Lifelong Milwaukeean here, I could write a book about it! I think it has almost everything you want, but I would not live here without a car because our public transit is terrible and our local governments have consistently taken pains to ensure that will never change.

I love to spend weekends in Chicago, I have tons of friends there, their music venues and record stores and restaurants and bookstores and museums are absolutely fantastic, it is outrageously easy to navigate and tons of interesting stuff is easily accessible by 24-hour rail, I'm extremely happy that I can take the Amtrak MKE-CHI commuter line -- Hiawatha -- there and back with zero fuss and similarly happy that O'Hare is only a shuttle bus away, I've easily visited a couple hundred times, but I would not live there for any amount of money or any reason because it is (to my mind) outrageously expensive and the masses of human and vehicle traffic make me want to bury a tunnel into the center of the earth and hide.

In my experience, you either "get" Chicago or you don't (and I don't); I would happily live in any of the other cities you mentioned, just not that one. Still, I wouldn't recommend making any kind of judgment on the city based on Navy Pier or The Loop because, as has already been noted by bona fide locals, they are largely miserable places to be.

A couple of Chicago publications that may help you learn more about the cool parts of the city: Gapers Block and RedEye. Chicago has a very devoted Yelp community, so clicking around over there will give you some general ideas as to where certain types of establishments and patrons tend to congregate. Lakeview is an outragously beautiful neighborhood, and an expensive one. Lincoln Park is perpetually ascendant. Wicker Park/Bucktown is super-hip. Ukrainian Village is (IMO) the best of all worlds. Here's a neighborhood guide to help you explore.

Excellent Ethiopian food can be found at Ethiopian Diamond and Ras Dashen. Head to Rogers Park and walk down Devon Avenue's Desi corridor to find incredible Indian food and groceries. Intelligentsia is the big local chain, but my favorite coffee shop is Wormhole in Wicker Park -- I'll never get sick of Six Corners the intersection of North, Milwaukee, and Damen.

If you really hate streets and neighborhoods that are laid out on a grid, and you want to live in a mostly-walkable place, Milwaukee and Madison might not be for you. As mentioned above, please check out Minneapolis! It has so very much of what you are looking for, and although it is not centrally located at all, MSP airport is a major hub for Delta so there are tons of direct flights all over the place. Minneapolis is the absolute best, and I would move there in a heartbeat if I didn't hate winter more than any other thing about life.
posted by divined by radio at 10:04 AM on January 16, 2014 [5 favorites]

I used to live in Ravenswood, and would recommend that over Evanston, where I went to grad school, if you are looking for all of the things you mentioned. Everyone else has covered some pretty good points, but I just wanted to add that for long runs you can run along the lakefront, and there's also the north shore channel trail that runs along the north branch of the Chicago river all the way to Evanston.
posted by ultraviolet catastrophe at 11:54 AM on January 16, 2014

The Cook County Forest Preserve areas and state parks like Starved Rock and Mathiessen and other little pockets of nature are better than nothing (I recommend this book) but they are nothing like what you will be used to from the east coast in terms of natural interest—everything is basically flat; areas are much more homogeneous in terms of flora; there are many fewer little streams and ponds; most of these areas are very small; and you are never (ever, ever) out of earshot of an interstate. You also inevitably have to drive through miles and miles and miles of sprawl to get to any of these places, and to get to them in any reasonable amount of time, you've got to do it on major highways in awful traffic. I think you would be much happier anywhere in Wisconsin.

The only outdoorsy things that I will miss when I move are the incredibly easy access to sailing and the beach.
posted by enn at 12:03 PM on January 16, 2014

I guess it depends where you're coming from. For me, Chicago was the perfect city. While cities like Boston were way too crowded, way too congested and way too expensive, I found Chicago downright convenient. Traffic is relatively good, mass transit worked great, everything is walkable, housing is affordable, and it's clean with beautiful architecture. I think everything you need probably is in Chicago in one of the suburbs outside the city, but if you don't want to be part of a huge metropolis (third largest city in the U.S.), then why do that to yourself?

Madison I know has the hiking and bars you're after and is much smaller. Plus, it's a pretty short drive to Chicago if you ever do get a hankering for the big city. You might also give Louisville a look. Pretty sure there is camping, bars, restaurants, etc. and Kentucky has a lot of charm. Louisville also isn't too far from Chicago.

I think living in a city is very different than visiting one. I enjoyed visiting Boston very very much, but despised living there. I enjoyed visiting Washington DC somewhat, and liked living there less. But if you don't even like visiting Chicago? It seems you probably won't enjoy living there. Chicago is my favorite city in the world, but I guess it's just not your cup of tea.
posted by AppleTurnover at 12:04 PM on January 16, 2014 [2 favorites]

I've lived in Chicago for 6 years in a mediocre neighborhood and my experience is as you say. I quickly ran out of things to do within walking/short bus distance (especially in the winter, ugh), and everything is far too spread out. There just isn't anything that makes me happy here-- a rarely find a jewel that I have to revisit, and I often end up at highly-regarded restaurants with very trendy decor that serve bland food without fresh ingredients. There's a pretty good Korean restaurant in my 'hood, but I have to travel almost two hours by public transit to get good Indian food. Japanese food, forget about it. I find the city to be without a whole lot of character, but it might just be that its character doesn't appeal to me so I don't appreciate it correctly. If I had to make a short list of things I really miss, at this point it would have maybe one item on it. My list for a city like DC is much longer.

A better neighborhood might make it awesome, but idk. My boyfriend and I have been talking a lot lately about finding a new place to call home-- Minneapolis has come up, as well as various places in California.

I was watching this thread with interest, but none of the responses so far have convinced me that I've been missing out or just haven't explored the right areas yet, so I think it might be a personality thing. I think it allso might just be that the sheer size of the city doesn't have a tangible payoff to me. If I'm going to live in a gigantic city, I want it to feel dense and innovative and on the edge-- Chicago is like the opposite of that. Spread out, and lagging behind both coasts, and it's hard to find that "fresh" element.

It's also cheaper than NYC or LA, but still fucking expensive, if you're not used to it. I do agree that the Loop and Navy Pier (actually I've never been here!) are probably not the best of the city. The walkable lakeshore is nice and I like the beach near where I live.
posted by stoneandstar at 12:35 PM on January 16, 2014

You want the Bay View neighborhood of Milwaukee. There's a kayak group that goes out on Lake Michigan when weather permits. Lots of indie coffee shops and quirky stores. Ethnic food is an easy bike or bus ride downtown. It's safe and cheaper than Chicago. Amtrak is nearby to take you to downtown Chicago or there's a bus to Ohare.
posted by desjardins at 12:41 PM on January 16, 2014

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)

just caught this... I lived in Montana for a few years until I moved back to Milwaukee and I grieved the loss of the mountains like I would a dear friend. It is just not going to be the same, and I'd plan trips to the mountains when you can. Illinois is not rugged at all; Wisconsin is heavily forested in the northern half, and the Apostle Islands are well known as a sea kayaking destination. Door County is much tamer but much closer to Milwaukee.
posted by desjardins at 12:55 PM on January 16, 2014

Stay where you are, regardless of where your respective families are located. I doubt you'll be particularly happy with anywhere in the midwest, so why ruin a good thing by moving? Some places may seem more or less like your style, but from what you describe I don't think any of them are actually going to be your style.
posted by aramaic at 1:27 PM on January 16, 2014

I've lived in Chicago my entire life and can't imagine anyone willingly moving here. I stay here because of my family and social network. You are completely right about Chicago.

Getting around Chicago is horrible. Traffic is a mess and public transportation is crime ridden. I rarely venture out of the city center, where I live. Traffic is just too terrible to go anywhere. The expressways are always clogged and the streets outside of the downtown area are filled with potholes.

The corruption is completely in your face. No one tries to hide anything. For instance, the mayor just added speed cameras all over the place (the idea coming about from one of his campaign contributors). The city is also dirty in general and except for the lake and skyline, there's nothing pretty about Chicago.

There are also people everywhere. Chicagoans are rather unpleasant and many are downright mean. I saw a women get hit by a bike recently and the biker just got back on his bike and pedaled off without even apologizing. I can list many more incidents of people being rude and uncaring than people actually being friendly.

Basically, if you are an inconsiderate jerk who smells bad and rides a bike everywhere, Chicago might be a good place for you.
posted by parakeetdog at 2:45 PM on January 16, 2014 [2 favorites]

You...should visit St. Louis. You can get everything you mention liking here, it's a great place to raise a family, and it's just a five-hour drive to Chicago.
posted by limeonaire at 3:04 PM on January 16, 2014

but from what you describe I don't think any of them are actually going to be your style.

I don't think this is true at all. I love the coastal cities but I love some smaller cities in the Midwest too for similar reasons. It really depends on what you value re: nature and how content you are tending your garden (metaphorically!). And if you value non-pretentiousness, the Midwest and cities like Minneapolis are not a bad bet. I'd give a couple cities a visit, tbh, and see if you like the vibe.
posted by stoneandstar at 5:44 PM on January 16, 2014

Just for the record, some of us Chicagoans are pretty nice, and smell okay. We don't even all own bikes.

That doesn't mean you should necessarily move here, though.

posted by like_a_friend at 11:13 PM on January 16, 2014 [8 favorites]

Getting around Chicago is horrible. Traffic is a mess and public transportation is crime ridden. I rarely venture out of the city center, where I live.

I've never had anything bad happen to me on a train or bus in my 7 years in the city. You live in the Loop and never leave, because of what, this idea that Chicago is like the movie The Warriors? If we drive, it takes us 30 minutes to drive from the upper north part of Chicago to the heart of the loop. That's pretty great.

Chicagoans are rather unpleasant and many are downright mean.... Basically, if you are an inconsiderate jerk who smells bad and rides a bike everywhere, Chicago might be a good place for you.

What? I can't even. Chicagoans are the nicest damn people I have encountered in my life. It is SO easy to make fascinating, dynamic, diverse friends here.

You've heard that saying about how if everyone you meet is an asshole, you should ask yourself what the common denominator is, right?
posted by Windigo at 1:35 PM on January 17, 2014 [12 favorites]

Wow, the people saying traffic and/or public transportation is horrible in Chicago or the city is too crowded really haven't lived in other cities. Chicago's traffic and congestion levels, especially for its size, are so much better than other cities I have lived in. All I can say to those people is try living in Boston. I guess it's all relative, and that is important. Most people want a place that reminds them of where they grew up or meets certain expectations of "the way things are," or they haven't lived in other places to recognize that the grass isn't always greener. I think the simplest first answer though is, if you're not a city person, don't live in a huge fucking city.
posted by AppleTurnover at 3:13 PM on January 18, 2014

I grew up in Chicago and surrounds, have lived in Milwaukee, and have been living in Ann Arbor for the past 28 years. I've traveled extensively in most of the other cities you've mentioned except MPLS. I love Chicago and can attest that it has every single one of the things on your list, including access to nature, except, as others have pointed out, if you are looking for mountains or oceans.

That said, I have had several opportunities to move back in the last thirty years and have not done so, primarily because of the hectic pace and the economic factors--as in, too many people chasing after the same basket of goods.

You might find, if circumstances forced Chicago on you, rather than the luxury of choice, that the grid layout, by Daniel Burnham, makes Chicago an extremely easy to navigate city. I lived most of my time there in the Oak Park-Berwyn area. I can still get from there to almost anywhere you can name in Cook County within an hour, even during rush hour. There is also no neighborhood I would NOT go to in Chicago, even after dark, but like any mid to large city, there are a lot of places I would not be in at 2 or 3 a.m., unlike Seoul, for example. Heck, the central campus area in Ann Arbor is one I would not be in alone after closing time (you can check out monthly and yearly crime statistics for Ann Arbor here).

Madison is eminently liveable, Iowa City too, probably, but I find them both too sterile and mono-cultural. Milwaukee I would live in again in a heartbeat. Great city. Lousy public transportation. Des Moines has probably the best Thai restaurant in the midwest, but I think you'd get tired of going to the same one, over and over. Chicago has more good to great restaurants than you can shake a fork at, even in outposts like Oak Park (a whole 15 minutes from the Loop).

Sorry for rambling here. If I were young again, say under 35, and had not grown up there, I would think that Chicago would be the ONLY place in the midwest that meets all of your criteria. I love the much-more-small-town feel of Ann Arbor, but frankly, if I were at that part of my trajectory, Ann Arbor would bore the heck out of me.
posted by beelzbubba at 8:41 AM on January 23, 2014

Getting around Chicago is horrible. Traffic is a mess and public transportation is crime ridden. I rarely venture out of the city center, where I live.

This doesn't match my experience. Bus tracking integrated with Google maps and all stops announced by onboard signs and loudspeaker makes getting around so easy it is ridiculous that people even drive! The closest I have come to any crime at all on transit is begging on the Blue Line out by Oak Park and I once saw a shell game con being run on the redline. That's in 18 months in the city without a car.

The corruption is completely in your face. No one tries to hide anything. For instance, the mayor just added speed cameras all over the place (the idea coming about from one of his campaign contributors). The city is also dirty in general and except for the lake and skyline, there's nothing pretty about Chicago.

Enforcing speeding laws is the opposite of corruption. Now the contract bidding is probably suspect and the use of the money will no doubt be political rather than practical (it is Chicago after all).

I've lived in something like 7 different cities (I'm too lazy to count) in 3 different cities. I'd rank Chicago as my second favourite place I have lived and it is only behind Toronto because I find it difficult to deal with the racism and American politics.

Navy Pier and around O'Hare are where I would take people I would want to never have return.
posted by srboisvert at 4:13 PM on February 6, 2014 [2 favorites]

I live in Evanston but grew up in New Jersey. Nature here is so lame I can hardly believe it. You're wrong about the food though. Look up the LTH forum.
posted by xammerboy at 9:01 PM on February 10, 2014

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