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Why New Yorkers Shouldn’t Look for Sweet Home in Chicago

A recent discussion thread in the popular, urbanist City-Data Forum asked readers for reasons why some people shouldn’t move to Chicago. That got me thinking about the time I encountered a pair of typical New Yorkers on my Marina City roofdeck. One of them was like me, a New Yorker who loves the rest of the world. The other was the kind of Gothamite the rest of the world loves to hate: a New Yorker who thinks everywhere else should be like New York.

Those are the New Yorkers who probably shouldn’t travel far beyond the safety of a 24-hour subway system. In answer to the question posed on City-Data, a good reason not to move to Chicago is if you’re a New Yorker like the above who can’t wrap your mind around the fact that every other major city on the planet doesn’t necessarily feel like the five boroughs.

Our skyline notwithstanding, compared to other popular, large U.S. cities (I’ll avoid just comparing us to the other Alpha cities, that would be too narrow a comparison), Chicago’s draw tends to be a bit esoteric. We’re the kind of city that it takes time to fully appreciate–and fall in love with. Not the least reasons for that being we tend to have a slower pace and a greater sense of modesty than other major U.S. cities.

A fair number of New Yorkers come to Chicago and most love the place. Some New Yorkers–like me, for instance–move here and decide to stay very happily forever. But some other New Yorkers visit here and spend hours complaining how Chicago is not New York. It’s annoying for Chicagoans and a great way to make no friends out of them.

Comparing and contrasting high-rise Chicago with high-rise New York is akin to sizing London up against Paris and complaining that one isn’t exactly like the other even though they’re both relatively low-rise world cities. It’s a category error my fellow New Yorkers make all the time–the assumption that only cities that feel as animated and crowded as New York can have huge high-rise skylines. That assumption may work for places like Hong Kong or Sao Paulo (not that we approach either of their populations in Chicago).

But the Windy City feels amazingly different than New York. Not just a little, but a hell of a lot different. Even with the Loop, 25 miles of lakefront skyscrapers, and a huge, old rapid-transit system, Chicago isn’t a little New York and never has been. Experiencing that coming-to-Jesus realization in person is probably the biggest reason some New Yorkers are so put out by Chicago. This city is confusing to them in ways they never expect.

It’s also probably not a good idea to move here if you’re afraid to wear longjohns, a hat, a scarf, and gloves. If I had a nickel for every visitor I’ve heard complain about our winters as they stood in the snow on State Street in a windbreaker, I’d be a rich blogger. I tell my New York friends when people move here and continue to dress like that, sometimes we just lead them to Lake Michigan and push them through the ice.

They actually think I’m kidding.

Categories: Chicagoans Chicagoland Urbanism

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Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

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20 replies

  1. I don’t know Chicago but I’ve passed through. I remember being on a bus leaving during rush hour and thinking this is a real city. I’ve traveled all over the USA and have been through many cities. It was interesting to read about new yorkers who complained. I had an opposite experience. I worked with a lady in nyc from Chicago who complained nonstop. She said she came to nyc to make money and was angry when she didn’t land a six figure job with no college education. To make a long story short, she drove the office so nuts (going as far as trying to get a single mom fired) that we told the boss. She found out and stormed off the job in a rage! Point of post, it goes both ways! In ny we get our share of those who come, hate it and blame the working class natives.

  2. Interesting post. I’m a born and raised Chicagoan, lived there for years as an adult before moving to NYC, where I live now, in 2001. I used to love Chicago, then grew to loathe it – but NYC has really worn me down to the point where I’m seriously considering giving up and moving back.

    I don’t mind the weather in Chicago, and I’ve realized that the urban density level is probably more my speed than that of NYC (which seems only to intensify with each passing year.) The food scene in Chicago is probably better than that in NYC. The lake is a great asset. The transit system is tolerable if not amazing (NYC is really in a league apart when it comes to US cities.) And of course, the cost of real estate in Chicago is so much more appealing than in NYC.

    My problem has always been with the people in Chicago. As someone who grew up in a reasonably affluent, Jewish area, Chicago always seemed to me like a cosmopolitan city – sort of a mini-New York with all the stuff but more manageable. But after college, when I moved out on my own, I began to realize that the city is much more a big Milwaukee. It’s filled mostly with ex-Midwestern suburbanites who don’t like to step outside their comfort zone and will ostracize you if you’re at all different.

    In NYC I hang out with people of different races, ethnicities, cultures, etc. In my running group alone, there are people from at least six countries I can think of off the top of my head. In Chicago, I found that pretty much everyone I knew was from the Midwest, or perhaps the South. In NYC most people I know have traveled internationally a fair bit – in Chicago, I sometimes felt like the only person I knew who had a passport and spoke other languages. In fact, I once had a guy take an active dislike to me solely because I spoke Spanish. He said it made me pretentious.

    As a gay guy, the gay scene in Chicago also made me want to sob. Pretty much everyone I knew spent their entire time getting wasted on Halsted. Every. Single. Weekend. Night. I’d try to get people to go to the Green Mill for jazz, or to explore a new neighborhood for ethnic food or whatever, and all everyone wanted to do was go to Roscoe’s and Sidetrack. Maybe Spin. Also, because the city is so filled with Midwestern transplants, the guys were often intensely closeted and self-loathing. In fact, one of the main reasons I wanted to move to NYC was because there I knew gay guys who – amazing! – had straight friends and didn’t live their lives entirely in a gay ghetto like the Halsted/Boystown strip. As someone who didn’t grow up in a hostile Christian environment, coming out wasn’t a particularly traumatic thing for me – and it honestly felt like I was in a minority of one on that score.

    Now, though, NYC has become an absolute playground for the global rich – a group in which I sadly do not belong. I currently live in far Upper Manhattan, in a neighborhood that’s amazingly being colonized by pretentious couples with organically-fed toddlers named Brianna and Allegra and Caleb… If I stay in NYC I’m thinking I’d end up moving to Jackson Heights and buying an apartment – which makes me think, why don’t I just move to Edgewater instead? I’ve got friends and people from way back in Chicago – probably more connections there than I do in NYC after all these years, actually.

    Yet I just have a great fear of doing that and finding myself back amidst the Indiana farm kids with no passports. And when I go back to visit Chicago, I see the same guys hanging out at the Caribou on Broadway at Aldine on Friday night – the same guys that hung out there then on Friday nights a decade ago, before going off to Sidetrack. Only now they have a baseball cap over their head to cover up the lack of hair. Sigh….

  3. For a guy who lives in NYC (20 years), Chicago (born and bred) and LA simultaneously. I can conclude: the pizza and hot dogs are hands down the best in CHICAGO! (just a fact and not part of the conversation thread).

    Love your comment, “It’s more like the city we always wished New York would be, if only it were friendlier, cleaner, and a lot less crowded.”

    I find Chicago is that great feeling you get on a Sunday at 8am in NYC – practically empty. Or when its a holiday and the only store open in the financial district is Century 21 (Just a few people walking around with those clear bags). Chicago is a summer day in Williamsburg BK taking in the food fest or concert venue and occasionally running into the cast of Gossip Girl. Which is akin to Chicago’s Wicker Park/Bucktown.

    Chicago’s Logan Square or Pilsen is New York’s Greenpoint or Bushwick. Chicago’s Evanston/Skokie is a tree lined Bayside, Queens moving into Douglaston L.I. heading down northern Blvd. New York’s Soho/Tribeca is our River North/West Loop and Manhattan’s Upper East/West Side is along our Gold Coast/Streeterville. But now I’m starting to feel it more in Millennium Park as it develops. Our Southampton or Connecticut runs along Kenilworth past the classic Ravinia Music Festival into Lake Forest.

    So anything a New Yorker wants in feeling/lifestyle, even if its as obscure as Ave K in Flatbush BK, you can find here in Chicago. The only place I can’t replicate is Coney Island 🙁 so if you’re from that whole Canarsie belt parkway loop heading to Verrazano bridge, your out of luck. Chicago’s Gurnee and Great America wont cut it and one could make a case for Navy Pier but I think it falls short in comparison.

    As for skyline beauty Chicago trumps NYC. It’s so well planned out that Chicago offers fantastic views from all around. You don’t have to cross over to the Brooklyn Heights Promenade to get a great view. And you don’t have to own a $1.5M one bed penthouse to see what’s going on. Even a rooftop deck in Chicago’s West Town commands a skyline view because of smart city planning. Chicago is truly the city that works. World class museums, sports and shopping. Chicago is where you live to live, New York is where you live to work, and LA is where you hope to work so you can live (hahaha just kidding cali).

    So in one word what’s great about NYC – EXCESS. It’s that crazy feeling of excitement one gets from seeing MORE. In all things from real estate, fashion, status, relationships, friendships, jobs, and generational compounded wealth. I just hope New Yorkers don’t let their life pass away chasing after these things, the next best thing is not always around the corner. Chicago is a place of balance. So trade the bodega for 7-eleven but if its a bodega you want, I know where they are. IT MY KIND OF TOWN! – ken watanabe @properties

    1. You win the award for best comment on a legacy post. I think your description of the thrill of seeing (and as you allude to, chasing) excess while your life potentially passes you be sums up New York City very well. It’s a big part of what pushed me away, and toward Chicago. If you had to confine yourself to one of the three cities you frequent, which would it be?

      1. Hahaha sorry for the late reply and thank you for the best comment award! Well that’s the problem, I can’t confine myself to just one city. I want Chicago to be located in New York with the weather of California (next to Manhattan would also be OK, maybe just plop Chicago down over Staten Island or Long Island City Queens).

        I see some real changes coming here in Chicago that makes me feel better about the progressive culture here. Chicago is still conservative in feel with most of its residents coming from places like Iowa, Ohio, Kentucky, Indiana, Michigan and Wisconsin. But with more improvements like Google/Motorola building headquarters here and more programs for artists in places such as Pilsen and Bridgeport, I see a more global cosmopolitan Chicago.

        If we can connect the West Loop with the cap the Kennedy park project:

        And continue to bring neighborhoods together with projects like The Bloomingdale Park Trail (much like NYC’s High Line Park):

        Chicago is really going to expand into neighborhoods that were once forgotten and already is. We need more westward expansion and I think people are not as scared to venture into these neighborhoods anymore. With so much space out here in the Midwest Chicago will rule one day as being a global city without the elitist mentality of NYC or LA. Gold Coast vs Logan Square, who cares. Upper East Side vs Queens biggggg difference in the minds of New Yorkers. And I think that pretty much sums up the difference.

        Thanks – Ken Watanabe @properties

          1. hey Michael, been very busy these past months since its the height of the real estate season. But as for LA, first congrats. Second I would stay away from downtown. LA is an entirely different animal, Chicago you want to be downtown, NYC downtown, LA in the burbs. You will learn quickly that the mentality there is for detached single family houses not condos. Yes you can find great lofts or mid-rise units within the city (downtown) but that’s not where most would want to be. Downtown has a high concentration of transient people (from all different backgrounds, ages and reasons to live on the street) they tend to harass you every time you step outside. I personally have no problems with this. But safety is a judgement one must make on their own. In fact the city of Chicago’s chief of police was sent to LA to handle the skid row area and downtown LA in general. There have been very militant tactics used here in Chicago and LA where the history of this struggle still exists.

            LA and California in general is still stuck in the hey day of old glamorous Hollywood. Not much has changed and for $1M+ you can get an old ranch style home or something that looks like a former taco bell and do your best to fix it up.

            As for value, check out silver lake, LA. If you have to be in downtown I like the art district or financial district. But as you know California is very spread out. Don’t be afraid to venture as far as Costa Mesa, New Port Beach, Irvine, Santa Ana or Huntington Beach, to find a nice reasonable place to live. Also don’t expect to find anything not short of a card board box. You are paying for the weather, culture, beach and location. Unfortunately not the property itself. Well..unless you have unlimited spending potential in which case you will find what you’re looking for.

            If you are planning to buy, wait. The California market is riddled with foreclosures. Many foreclosures have not hit the market but are being trickled out slowly to keep values high. Its the wild west over there so be careful. California is a Title State, the lending institution holds title to the property in the name of the borrower through a Deed of Trust. So there is no judicial process and banks love to take the house. Where as here in Chicago you in theory hold title and a bank places a lien on your house until its paid. If they want to take it they must go through the court system in which case one has some time to remedy the crisis.

            If you are renting, just as in NYC, find someone who is already renting out there and get some feedback. There are many shady landlords who will take advantage of out-of-state transfers. They own a handful of properties and prices skyrocket when you’re in need to move for a job. Also unlike any place I have known, carpet!!! is where you don’t get your deposit back. You will be charged for new carpet pro-rated to the useful life of the carpet when it was first installed. Even reputable rental bulidings will do this. Some will not take a deposit and two weeks before lease end, you will get a bill for the entire deposit for carpet replacement. Not like you wanted the carpet anyway!! but like I said, everything is 1950’s and wall to wall carpet was and still thrives over there.

            Good luck buddy and feel free to send me any questions.


    2. Ken, that comparison is spot on. I’m a Manhattanite who is contemplating a move to Chicago. I love NYC for it’s insanity but I love Chicago for its normalcy. The idea of taking a train or strolling around that doesn’t involve a screaming crackhead or a throng of elbow jabs is quite enticing. But yeah, Coney Island. Love that place. And find it really hard to imagine a life without the Mermaid Parade. Does Chicago have any weird and quirky parades? And what about a music scene? A typical night for me would be heading to the Lower East Side or Williamsburg for a little indie show. I’m putting together my pros and cons list now before I commit to a move. Thanks!

      1. Hey Lauren,

        I’m always surprised what I can tolerate in NYC that I cannot anywhere else. I do have to say, when taking the train here in Chicago I am personally more afraid then in NYC. Even though there may be a screaming crackhead at 4am heading back on the “L” train, there are enough sane people on the train to make me feel safe. Here in Chicago I have seen more strange people, screaming people and fights than in NYC. Moreover, the train stops are spread apart in Chicago and in general more desolate, making getting off not easy. You know the feeling when the AC is not working and you jump out at the next stop and changes cars, or the smelly drunk guy just pissed his pants and you realize the stink is why that particular car is empty but the rest of the train is packed.

        I hang out with all different types of people in NYC from the BX to UES down to LES to BK, I am always all over the place and for some reason I never feel at risk.

        As for the little indie show…hummm its kind of here but not. You wont find the next MGMT, arcade fire, yeah yeah yeah’s when they’re unknown. There won’t be a williamsburg concert packed along the promenade with all the big names. Or the dinky LES drinking hole with awesome music. You will get a version of everything here in Chicago. Maybe a street fair with live music in Logan Square. Maybe a version of a dive bar with a mix of blues, indie, industrial and punk. But its never just want you want. There will be that parade that you find quirky but not shocking.

        One has to remember that Chicago is the big city for places like Wisconsin, Kentucky, Indiana, Ohio, Iowa. This is a relatively conservative crowd. One may disagree with me but I find Chicago a more humble place, where anything over the top is not considered WOW! but more ieeekkkk what a show off! who do they think they are?….But that’s not everyone.

        To sum it up, for your check list, you are trading the weird bodega that you have grown to love, where they know you and will spot you a coffee and muffin since you have no cash for Chicago and 7-eleven (a chain corner store which actually just opened in NYC on 8th ave and 38th street). You are trading, reinventing yourself with no rules in NYC for fighting against the molds people want to put you in – here in Chicago. You are trading, that hidden underground bar and pancakes with borscht at Veselka for a corporate run franchised bar that advertises itself with stereotypical handle bar mustaches and indie themes so it can fit into a “hip” demographic. Late night pancakes will come from IHOP.

        So why move to Chicago? well as for real life…most people don’t actually have a real life in NYC (a little exaggeration). They have a fictitious one they live daily. They have a relationship they live monthly, home rented again monthly for some weekly, Some have 6-figure+ salaries that are completely spent yearly, but most don’t own anything, don’t fully love anything of value or are too busy to contemplate the future. The “new york death” is imminent for them.

        Why do I love NYC, for all the same reasons I said above. You don’t own anything, things are always changing which can be exciting, you feel alive when you are struggling, hope, achievement and dreams are what people wake up for. If you get it great! if you don’t, you live in nyc and will learn to survive. But as you reach for the next level you learn to appreciate a small drink, a nice coffee, an empty nyc in the summer, and small things.

        Bottom line – after your move to Chicago, you will always want to live someplace else, you will have to search for versions of what you loved in nyc, you will progress in “real” life here in Chicago, you will finally have a chance to breath here in Chicago, but you will miss the fantasy of what could have been in NYC. Unfortunately there is no defining answer of what is enough….because in nyc there is never enough…only MORE.

        Just my opinion obviously it will be what you make of it. Others may think differently.

        I love NYC, LA and Chicago for different reasons. Which is why I will always be living between all three.

  4. Hello,

    Yeah comparing the two cities is futile. They are similar in some ways and yet very very different.

    I moved to Chicago after living in NYC up until my late 20s. I came to Chicago for my career and a higher standard of living..but I stay because Chicago is beautiful, the lifestyle is great, the food is awesome and cheap, oh and ease of meeting fun people. I met my wife here and I will never leave, of course I love to travel and use ORD as my door to the world. I typically have to go up to Skokie and the northshore for good bagels and delis…but they are there and I don’t crave either all that often.


  5. To think I moved here from Buffalo for the weather! I describe myself as a Western New Yorker, someone who south and west siders couldn’t understand on the phone when I first moved here 13 years ago. I look at it this way I’ve sort of joined the other side, back home pre-9/11 there was the NYC and the rest of the state way of thinking. Well that’s changed. Here there is Chicago and the rest of the state, well I’ve become part of the big city population, the rest of the state. With the pension crisis that is getting worse.

    Anyway, I still can’t figure it out, what is the big deal about Chicago winters? Compared to Buffalo? OK there is nowhere to put the snow but for the rest, well they just don’t get that much here. No long subzero, dark days January through April. Wimps!

    1. I’m not sure, Jane, but did your post have a point that’s relevant to the topic besides not thinking Chicago’s winter’s aren’t so bad? Lookie here people, we have a tough NYer here! Move outa the way.

  6. David, the bars (of all persuasions) are way friendlier here than in NYC, where it’s a perpetual meet and meat market. Here, people will talk to you as a person where in NYC the other person’s eyes will always be glancing behind you to see if there’s someone more attractive (or, ahem, richer) to be talking to. (Of course, this may be an apt description of bars in Chicago’s Viagra triangle!)

    I will attest to that feeling of going back to NYC to visit, only to remember WHY–YOU–LEFT in the first place. Chicago isn’t boring for a New Yorker. It’s more like the city we always wished New York would be, if only it were friendlier, cleaner, and a lot less crowded. Trust me, for some Gothamites, Chicago sells itself.

  7. Interesting take. I have a couple of friends born and raised in NYC that moved from NYC to Chicago after spending just one weekend here. Albeit a summer weekend. They were amazed that you could drink out on the streets at our festivals and according to them, some of the bars they went to were nothing like the ones they have in NY. And these were bars that I would consider typical. But regardless, they got jobs here and moved. Almost a year later, still here.

    In the beginning I did feel pressure to show them a great time every weekend, etc. because I felt the pressure of Chicago becoming dull and not being NYC. But after time they began to take Chicago for what it is. Almost a small town in a big city. After going back to NYC one weekend they mentioned that they couldnt wait to get back and that they were kind of over NYC.

    I dont know how long they will stay but so far they seem to have gained the same love for Chicago as you have. I am very proud of being born and raised in Chicago and love that others from different parts of the country can feel the same.

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