Whether or not you’ve been there, what do you associate the city with?

41 comments
  1. It’s probably my third favorite big city, but as a country boy and I don’t have a very high opinion of big cities to begin with.

    It’s cool, though. Good food, good culture, and not so big that is completely overwhelming.

  2. Been there. I like it a lot. I think the only place, not on a coast, that I loved so much I’d consider living there.

    Really friendly. Fun. Good food. Such incredible history.

  3. I really like it and not just because I was born there. It’s super pretty basically everywhere, the food scene is top-notch, and there’s so much to do. I always enjoy it each time I visit.

  4. I’m in Chicago right now. Great food, great lakefront access. Beautiful architecture. B+ on public transit. Museums are awesome but generally pricey.

  5. It’s an outstanding city. Great food (pizza, italian my favorites). Wonderful museums, probably 2nd best in the country to DC. The skyline and the lake are stunning. The violence gets a bad wrap, but it’s mainly confined to the south side.

  6. Incredible city. Beautiful.

    confused pizza.

    would live there, much more affordable than New York.

  7. Great museums, chilly in the winter, some tasty but generally heavy food, and based on my short visit I think Malört is a tasty beverage.

  8. Been there for a couple business conventions pre-covid. Great pizza and never felt dangerous despite the hype.

  9. It’s just a big Milwaukee.

    Also one of America’s great cities. Which is why I live here. People who associate with it crime and corruption love to hate on it because it’s associated with Obama. They obsess over all the horrible horrible CRIME!!!!!

    People who do that have probably barely left the small town they grew up in and don’t even know what a city is. But if Chicago wasn’t great, all those people wouldn’t choose to live in it.

  10. I lived there a long time.

    Beautiful. Lots of interesting things to do. Great food and people.

    Winter is tough, but you get used to it.

    The crime thing is overstated.

    And the city is entirely corrupt. Infrastructure falling apart. Cops are horrible. Taxes are insanely high. And the state pension is basically insolvent and politicians just keep ignoring it and giving handouts to their cronies.

    I was glad to move.

  11. Been there a bunch. Love the eastern/rust belt-y feel to much of the city (you don’t get that a ton in the midwest or west), but yet it’s still vibrant and alive.

    Great diversity, cool culture, great art, wonderful parks and public spaces. Good public transit for most of the city and the inner suburbs.

    It’s just a bit too cold and windy (yes, I know it’s not called the Windy City because of its climate but because of its politicians… but it’s still windy at the lakeshore), and the city hasn’t done a good job of protecting visitors and citizens from the elements during the winter (the way that, say Minneapolis has with its Skyway system).

    What do I associate it with?

    – All the stuff in Ferris Buehler’s Day Off (the Cubs, the Chicago Merc, the Art Institute, parades)

    – Food in general (Pizza, dogs, hot beef, sausage, fine dining, tons of ethnic food and everything in between)

    – Big sports town with diehard fans (Cubs, Sox, Bears, Bulls, Blackhawks, Fire)

    – Corrupt government / machine politics

    – Transit & Transportation — the El, O’Hare, Midway, the amazing expressway system and all the goods traveling in, around, and through it.

    – Its skyline and architecture

    – The river and its greenness during St. Patty’s day.

  12. I wish I could’ve spent more time in the city. I was there once for a single day – spent it at a business convention. It’s the only other city I’ve visited that gives NYC vibes.

  13. The art institute is an amazing place several years ago maybe 10 they added the modern wing, a Renzo piano design marrying old with new. Truly beautiful and it butts up to lurid gardens and then there is the bridge down to millennial plaza, beautiful place.

  14. I went to Chicago once and tbh I had no idea what to expect. It was awesome, I loved it. Great music, ppl were much friendlier than other big cities like New York and Boston, food was great too. You gotta try some Deep Dish pizza and stop by Gibsons as well.

  15. Probably the greatest city in the world (minus the wild weather). Great food, great people.

  16. Been there. We went to a concert, stayed overnight because it’s a long drive from where we live.

    I liked walking everywhere, and public transit. Food is amazing. People were cool, and the first question I got as soon as I said anything was, “Where are you from? I love your accent!”

    It was fun to sit in a restaurant and people watch. Chicago is a great place to do that. The park is also good for that.

    I want to go back and visit museums and do cemetery tours.

  17. Chicagoian for almost my whole life. Whenever I visit other cities they always think buildings are on fire and crime is just running amuck. Crime is bad , but not fear for my life bad. Just pay attention to your surroundings and you’ll be good! Tons of amazing food, as many have stated. Not just Pizza, we have some of the best steakhouses in the world!

  18. Love it!! I’ve traveled there by Amtrack, quite a few times. No car needed, wheel your luggage to your hotel and then let the party begin. They have transit system and many places in walking distance or even boat to.

  19. My late husband was a born and bred cheese head so I always here his voice saying “the bears still suck.. look at the person driving insane…fucking FIB’s (short for fucking Illinois Bastards)”.

  20. My favorite large urban city. Best hotdog in America. Great food. Great music. Really good public transportation. Love the L. Very walkable. Nice parks. Great sports culture too. Just an awesome city.

  21. The shining city on the lake.

    The greatest city in the US.

    I love Chicago.

    I loved living there.

  22. Right next to NYC as the quintessential All-American™ city IMHO. Rich history, culture, food, architecture, industry, and on and on

  23. Immigrants here. Chicago was what I thought the land of USA look like thru movies before I moved here. Old school buildings, snow and lights on Christmas, lots of people walking on the street, chilling weather and everyone looks happy in their warm jackets. That movie “Home Alone” was my impression of Chicago.

    Well when I first set my foot into the US in 2014 at George Bush Intl Airport in Houston in the middle of the scorching August let’s just say I’m disappointed.

  24. I like Chicago quite a bit. They have good food, great museums and architecture and a beautiful lakefront. It’s, probably, my favorite big American city and the only one that I would want to live in full time.

  25. Never been but want to go when I think of Chicago I think of

    Amazing skyline, great history, great Italian/polish food, and Crime

  26. Lived in or near Chicago for most of my life. I love it so much. There’s more good food and entertainment options than I’ll ever have the chance to try in multiple lifetimes. The urban green space is unrivaled too. And it’s also insanely affordable to live here compared to the coasts. So I think I have a pretty positive impression.

    Guess my only real gripe is that it’d be cool if we had some wilderness land nearby.

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