I'm simply obsessed with Chicago

destroycreate · #1 Posted **Aug 1, 2025, 7:23 PM**

Currently in Chicago for work—first time back since 2018—and wow, this might be the cleanest major city in America. Even the CTA trains feel well-kept.

The people are friendly, the vibe is unpretentious, and the downtown/architecture is epic (no news there). What strikes me about the buildings is how absolutely colossal in scale they are. I'm also happy to see the Loop busy post-pandemic...I'd heard a lot about how it had become a ghost down for a while, but from what I can see, the downtown feels very busy and vibrant again with plenty of office workers about.

I also love the endless lakefront parkland that goes up the coast. It's very well maintained and manicured.

I’ve been staying up in Lakeview and now Ravenswood—so many young people around. And the affordability here is wild. Yesterday I grabbed a sandwich for $12. In LA that same sandwich would be pushing $20.

I genuinely don’t get why this city isn’t more of an international destination or why more coastal folks aren’t moving here en masse. Real estate is shockingly affordable by comparison. Yes, the winters are harsh, but come on—bundle up and deal with it. I'm strongly considering buying a condo here (I've seen prices for condos $200k-$400k in really nice areas) and renting it out since I can't afford real estate in LA at the moment.

Chicagoans, you should be proud. This city is so underrated for the punch it packs. Hope to spend more time here in thanks to new clients that I have here.

Yuri · #2 Posted **Aug 1, 2025, 7:32 PM**

+1

I also got Chicago's fever last month. I completely fell in love with it.

And I agree with all the reasons you provided: people are amazing and indeed unpretentions, the city is well kept and so beautiful, even though it's not edgy it's very open minded and pleasant.

craigs · #3 Posted **Aug 1, 2025, 7:38 PM**

Chicago is a city worthy of obsession, especially for urbanists. It's got the total package.

LA21st · #4 Posted **Aug 1, 2025, 8:26 PM**

I lived there for 10 years, it's one of my favorites. Top 3 for sure. Or 2.
I worked in the middle of the loop and lived by the Hancock tower for 4. I go back to visit friends every year. Was just there. Its not a ghost town like 2021 ( I saw it firsthand) but its not the same Chicago pre covid. To be fair, no city is.
Im glad to see it improving. It will always be a home.

But the weather is no joke. It shouldnt be taken lightly and it does affect how you traverse the city in those months. Its not the same city during the late fall to like ...May. Either its still cool/windy and or less sun. The greyness does get to you. I dont even love the sun but there can be weeks where it never comes out. Some people love that. Many dont.
I visited in October a couple of years ago and was reminded its just a constant, chilling wind. Can you wear a jacket? Sure. But you're less likely to walk around more, enjoy the lakefront, etc etc. This isnt a Chicago thing, I go back east for Thanksgiving and its the same obstacle of bad weather making you want to stay inside.

People aren't moving from the coasts mostly because of this reason, plus lack of better terrain/scenery etc. Some friends have asked about Chicago and I say it has alot going for it, but Im not gonna lie and brush off the cold. Visit there and December and then post this question. You'd understand.

Crawford · #5 Posted **Aug 1, 2025, 8:45 PM**

It's a world-class city, an American gem and extremely well-rounded, doing quite well in almost everything.

It isn't remotely clean (never understood that one) and its comparatively low(er) RE prices are pretty self explanatory. Chicago has had terrible RE returns; easily the worst among the biggest U.S. cities.

James Bond Agent 007 · #6 Posted **Aug 1, 2025, 9:17 PM**

Quote:

Originally Posted by destroycreate

I genuinely don’t get why this city isn’t more of an international destination or why more coastal folks aren’t moving here en masse.

Cold and snowy.

Plus, the right-wingers will complain about the taxes.

mhays · #7 Posted **Aug 1, 2025, 9:49 PM**

I'd absolutely consider it if I was moving (not that I am). The mix of urban greatness, transit, lower cost, and fantastic air connections would go a long way. That said, the extreme heat and cold (vs. the mild PNW) would be a significant downside; for half of the year long walks would be unpleasant.

Steely Dan · #8 Posted **Aug 1, 2025, 9:59 PM**

Quote:

Originally Posted by destroycreate

I genuinely don’t get why this city isn’t more of an international destination or why more coastal folks aren’t moving here en masse.

1. Sexy people like sexy things. Chicago ain't sexy.

2. The winters are NO fucking joke (for pussies).

3. You gonna get shot!!!!!!!

LA21st · #9 Posted **Aug 1, 2025, 10:51 PM**

Quote:

Originally Posted by Steely Dan

1. Sexy people like sexy things. Chicago ain't sexy.

2. The winters are NO fucking joke (for pussies).

3. You gonna get shot!!!!!!!

Nah, there's plenty of tough guys in Chicago who can't stand that shit.
And judging by how many people are actualy outside in those bad temps, I guess most of Chicago are pussies then.

Dude I lived there for 10 years. Most people hate that shit. They wait until its over and enjoy the warmer weather. Thats why Chicago is so full of life in the summer, because theyre taking advantage.

If you like it, good for you. Some do.

Steely Dan · #10 Posted **Aug 1, 2025, 10:55 PM**

Quote:

Originally Posted by LA21st

Nah, there's plenty of tough guys in Chicago who can't stand that shit.

What do you mean by "nah"?

If you can't handle a Chicago winter, you ain't "tough". Full stop.

I never claimed Chicago wasn't chock full of pussies.

It most obviously is going by the way people here never stop bitching about cold weather in the winter.

The vast majority of people everywhere around our globe are pussies when it comes to cold weather.

SIGSEGV · #11 Posted **Aug 1, 2025, 11:07 PM**

Well, it's ESPECIALLY busy now downtown because of Lolla.

Steely Dan · #12 Posted **Aug 1, 2025, 11:10 PM**

Quote:

Originally Posted by SIGSEGV

Well, it's ESPECIALLY busy now downtown because of Lolla.

Yeah, no kidding. Walking west to OTC from my job in the central loop after work this afternoon, there were streams of Lolla kids going the opposite direction.

For once it looks like they might finally have nice weather thru the weekend.

SIGSEGV · #13 Posted **Aug 1, 2025, 11:12 PM**

Quote:

Originally Posted by LA21st

Nah, there's plenty of tough guys in Chicago who can't stand that shit.
And judging by how many people are actualy outside in those bad temps, I guess most of Chicago are pussies then.

Dude I lived there for 10 years. Most people hate that shit. They wait until its over and enjoy the warmer weather. Thats why Chicago is so full of life in the summer, because theyre taking advantage.

If you like it, good for you. Some do.

The worst weather in Chicago is during the summer, IMO. Like last week when it was like a million degrees outside followed by drenching rain.

Steely Dan · #14 Posted **Aug 1, 2025, 11:16 PM**

Quote:

Originally Posted by SIGSEGV

The worst weather in Chicago is during the summer, IMO. Like last week when it was like a million degrees outside followed by drenching rain.

Ditto.

I'd MUCH rather go for a walk in Chicago on a cold January day than one of those stupid-ass humidity festivals like we had last week.

I can dress for cold.

But a 78 degree dew point....... you done fucked!

LA21st · #15 Posted **Aug 1, 2025, 11:21 PM**

Quote:

Originally Posted by SIGSEGV

The worst weather in Chicago is during the summer, IMO. Like last week when it was like a million degrees outside followed by drenching rain.

There was bad day around July 10th this year that felt like Texas or something. Ill give you that. I didnt want to walk around much in that either.

But most of my trip was decent, not sufferable humid stuff. I wanted to see more thunderstorms actually.

destroycreate · #16 Posted **Aug 1, 2025, 11:25 PM**

Quote:

Originally Posted by jackb

NO WAY I just saw this post on reddit, like 2 mins before seeing this. Are you gueritoaarhus?

I love Reddit!

SIGSEGV · #17 Posted **Aug 1, 2025, 11:35 PM**

Quote:

Originally Posted by Crawford

It isn't remotely clean (never understood that one).

Have you been to LA lately?

LA21st · #18 Posted **Aug 2, 2025, 12:06 AM**

Quote:

Originally Posted by SIGSEGV

Have you been to LA lately?

Depends where? Most of LA doesnt look like downtown or hollywood, Westlake or what not.

I live in Studio City and this entire part of the valley is as clean or cleaner than chicago. I could rattle a TON of LA neighborhoods that arent problematic in that sense.
Hell even a good chunk of Hollywood is clean (outside of Sunset and Hollywood blvd).

In terms of core Chicago is cleaner. By city it might be cleaner. Chicago is cleaner than most, yes. But don't try all of LA is dirty. That's bs.
Even in some of the poor neighborhoods, many of those residential streets are well kept.

MonkeyRonin · #19 Posted **Aug 2, 2025, 12:15 AM**

Quote:

Originally Posted by Steely Dan

Ditto.

I'd MUCH rather go for a walk in Chicago on a cold January day than one of those stupid-ass humidity festivals like we had last week.

I can dress for cold.

But a 78 degree dew point....... you done fucked!

Being from Toronto (which is very similar to Chicago's climate), I don't find the winter weather bad at all. It's the length of the winters and overall sense of dreariness that sets in by late winter/early spring that get to me, on the other hand. December-February is fine, but when it starts dragging on into March or April it can get a little depressing.

SIGSEGV · #20 Posted **Aug 2, 2025, 2:18 AM**

Quote:

Originally Posted by LA21st

Depends where? Most of LA doesnt look like downtown or hollywood, Westlake or what not.

I live in Studio City and this entire part of the valley is as clean or cleaner than chicago. I could rattle a TON of LA neighborhoods that arent problematic in that sense.
Hell even a good chunk of Hollywood is clean (outside of Sunset and Hollywood blvd).

In terms of core Chicago is cleaner. By city it might be cleaner. Chicago is cleaner than most, yes. But don't try all of LA is dirty. That's bs.
Even in some of the poor neighborhoods, many of those residential streets are well kept.

Oh I totally agree, but OP is from LA (I think?) so that's probably why he thinks "clean" is warranted. Chicago is definitely no Stockholm or Copenhagen though...