Hey fellow Chicagoans!
If you scroll through threads on Reddit about Chicago, you’ll start to notice a pattern in how we talk about our city. We’ll complain about the weather in one thread, but then brag about summer festivals right after. We love dumping on the CTA, but we’ll defend the lakefront like it’s our civic duty.
That’s the thing about Chicago, people don’t hate it from a distance. They criticize it because they live it every day. Because the closer you are to something, the easier it is to talk about its imperfections. And if anyone gets to talk badly about our city, it should be us, right?
We’re the Ben Lalez Team, and although we spend most of our time helping people buy and sell in every corner of Chicago, we also sometimes get annoyed at things in the city.
So we went through hundreds of Reddit threads to find the most common frustrations people share about living here. The comments aren’t from outsiders. They’re from the people who know Chicago best… all of us.
While we found a TON of stuff, these were the most recurring, and the ones we think you’ll nod your head in agreement with.
Let’s get started!
Getting Around Chicago Isn’t Easy Sometimes
If there’s one topic that comes up again and again, it’s the struggle with getting around the city. Chicago is a city that looks connected on paper, but often doesn’t feel that way when you’re late and trying to get somewhere fast.
Driving can be an absolute nightmare. Construction never ends, traffic is chaotic, and some drivers act like they’re auditioning for a car chase scene. If you pick the wrong time to run a quick errand, it can easily turn into a 45-minute detour.
With expensive parking and streets full of potholes, it’s not hard to see why people get frustrated (and we’re not even talking about when there’s snow on the streets).
Public transit, once one of the city’s biggest strengths, is struggling too. On Reddit, riders complain about long waits, cancelled trains, and safety concerns. The frustrating part is that some days the system feels fine, while on others it feels like it’s barely holding together.
Still, for all the complaints, most Chicagoans agree on one thing. When transit works, it’s what makes the city livable. You can leave your car behind, get anywhere with a single transfer, and feel like the city is yours. The problem is that it just doesn’t work often enough.
Winter Lasts FOREVER
Okay, not foreverrr, but almost every conversation about what people hate about Chicago leads back to the same thing: the winter.
It’s long, it’s gray, and it’s difficult.
Locals talk about weeks without sunlight, winds that make your eyes water, and a “spring” that feels like a rumor until around June.
Even those who grew up here say it tests their patience. Still, there’s a shared sense of pride that comes with surviving it.
And then the first warm day of April feels like a holiday. Sidewalk cafes reopen, lake paths get busy, and people start smiling at strangers again.
Rising Cost of Living
Chicago’s affordability used to be one of its strongest selling points. We were known as a big city where you could still live comfortably, but that’s changing now. Rent is climbing fast, property taxes are just too much, and groceries, gas, and utilities all cost more than they did just a few years ago.
People often describe it as being “nickel-and-dimed.” There’s a tax for everything, from drinks to parking to streaming services. We’re paying, but we’re certainly vocal about how we don’t like it.
But compared to other big cities, Chicago still feels like a deal. You can have space, culture, and access to world-class restaurants without paying Manhattan prices!
Politics That Test Your Patience
Chicago’s political reputation is well known (and not in a good way). People here are just tired of corruption headlines, endless tax increases, and budgets that never seem to balance.
For many of us, it’s not anger so much as resignation. We expect things to work, but we also expect to be disappointed.
Still, there’s a reason people care enough to keep arguing about it. We all want the city to do better because we believe it can.
Every once in a while, improvements do happen – things like new bike lanes, park renovations, and small business programs that actually help. Those moments remind people that progress isn’t impossible. We just gotta be patient.
A Beautiful City Struggling to Stay Clean
Chicago is one of the best-looking cities in the country with its skyline, lakefront, and old brick buildings. There’s just something about Chicago’s character that can’t be found anywhere else in America.
But walk through enough neighborhoods and you’ll see the gap between the image and the reality.
Redditors complain about litter, cracked sidewalks, overflowing trash bins, and alleyways that never seem to get cleaned. In some areas, rats are more common than pigeons.
This isn’t about vanity. We all take pride in where we live, and when the city looks neglected, it feels personal to us. The frustration comes from wanting Chicago to look like it deserves to.
We don’t expect it to be perfect, but we do want it to be cared for.
Making Friends is Hard
Chicagoans are generally polite people, but it can take a while to move past surface-level friendliness. Many newcomers to the city say it feels like everyone already has their circle – people they met in college, through work, or growing up here.
Once you break through, friendships are real and dependable, but getting there can take a lot of effort, and some people are having a tough time connecting.
That slower pace of connection might frustrate some, but it’s also part of what makes relationships here solid. Because once you’re in, you’re in!
Nature is Lacking
Chicago has parks, trails, and of course, the lakefront, but beyond that, access to nature is fairly limited. The flat geography means you won’t find mountains, and real wilderness requires a road trip outside of the city.
Still, the lakefront remains one of the city’s best features.
It’s free, open, and stunning no matter how many times you see it. On summer mornings, it’s full of runners, cyclists, and dog walkers, and it’s a happy place for a lot of residents.
Little Things That Wear on You
Chicago’s food scene has a national reputation, and it’s well earned, but locals still find plenty to complain about.
Bad bagels, restaurants that close early, and a lack of corner stores compared to New York. Some also say that certain neighborhoods feel overbuilt, while others get ignored. Downtown might have luxury towers and trendy restaurants, but head a few miles in any direction and you can feel the difference.
But we think these small frustrations don’t cancel out the good things. It’s all part of being a big city. Some things are world-class, and other areas could do with some improvement. Totally normal if you ask us.
When the Romance Wears Off
A lot of Reddit posts don’t sound angry, they sound disappointed. They’re people who wanted to love Chicago, who moved here because it felt like a place with opportunity, energy, or some kind of magic they couldn’t find elsewhere. But living here day to day isn’t what they imagined.
Many describe the same story of arriving full of excitement, and for a while, Chicago is awesome. There’s always something happening, the city feels big and full of promise, and the summers make everything worth it.
But then the routines set in. The commutes get longer, the winters are terrible, and the gap between what they pictured and what they experience starts to widen.
What’s interesting about these posts is that they’re not about regret as much as reality. Chicago is easy to fall in love with from a distance, but living here means learning that love comes with effort.
What Does This All Mean?
Whenever you go looking for opinions online, the loudest voices are usually the ones with complaints. People rarely make a post just to say everything’s fine.
And, like any major city, Chicago has its challenges: aging infrastructure, affordability, and political issues that frustrate residents. But come on, none of it is unique just to our city. Every big city in America is working through its own version of the same problems.
What stood out while going through all those Reddit threads wasn’t how much people disliked Chicago, but how much they still cared about it. For every post venting about potholes or taxes, there were several more talking about the lakefront in summer, the food, the neighborhoods, and the sense of pride that keeps people here.
That part deserves its own spotlight, so in our next article, we’ll share what people say they love about living in Chicago, straight from the same threads.
In the meantime, if you’re thinking about making Chicago your home, or you’re thinking about switching neighborhoods, we can help you see both sides of the city. We know its challenges, but we also know what makes it the best place to call home. Give us a shout and let’s talk!
Sources:
https://www.reddit.com/r/chicago/comments/17gz93o/what_do_you_dislike_about_chicago/
https://www.reddit.com/r/SameGrassButGreener/comments/1b7p9jw/those_of_you_who_moved_to_chicago_how_do_you_like/
https://www.reddit.com/r/rant/comments/14krdjt/chicago_sucks/
https://www.reddit.com/r/chicago/comments/pppgl2/serious_answers_only_please_whats_it_like_living/
https://www.reddit.com/r/SameGrassButGreener/comments/1l2kuqu/okay_whats_wrong_with_chicago/
https://www.reddit.com/r/chicago/comments/amzupo/whats_the_best_and_worst_things_about_living_in/
https://www.reddit.com/r/chicago/comments/w3fvly/can_i_be_honest_i_fucking_hate_it_here_you/
https://www.reddit.com/r/chicago/comments/xvfd9t/what_is_one_thing_you_love_and_one_thing_you_hate/
https://www.reddit.com/r/AskChicago/comments/1hwb0a7/on_a_scale_of_one_to_ten_how_well_do_you_like/
https://www.reddit.com/r/AskChicago/comments/1mhqwb1/whats_the_reality_of_living_in_chicago_like/
https://www.reddit.com/r/chicago/comments/173yql6/what_do_you_wish_you_had_known_before_moving_to/
https://www.reddit.com/r/AskChicago/comments/1mts54a/how_does_it_feel_to_live_in_chicago/
https://www.reddit.com/r/AskChicago/comments/1bv2s75/are_people_in_chicago_more_real/
https://www.reddit.com/r/chicago/comments/y452mj/why_dont_more_people_move_to_this_city/
https://www.reddit.com/r/AskChicago/comments/1iigyo1/why_not_move_to_chicago_what_are_the_real/
https://www.reddit.com/r/AskChicago/comments/1mvow7e/everyone_loves_chicago_but_i_just_dont_what_am_i/
https://www.reddit.com/r/AskChicago/comments/1e23nob/chicago_pros_and_cons/
