I also think most of the architecture on the north side is really charming --- every block is a shaded corridor of dense tree cover with a mix of old and new 2-3 storey walk-up buildings and mixed-use on the corners. The north/northeast side is my happy place, and a starter home in Jeff Park or Portage Park will set you back ~275-300k, for neighborhoods where all the lots have back yards and everything's walking distance from the Blue Line.
But it's true, that's as compared to New York or San Francisco. There are certainly better deals elsewhere in the country!
This is often brought up, often by very vocal people on r/chicago, but I've lived in Chicago for years and have never missed nature. The lake is good enough for me. I suspect there are a ton of people like me. I grew up in a big city and I'm energized by the energy of big cities. I like green spaces, but I don't actually feel a compelling need to be in wilderness.
Indiana Dunes National Park is less than an hour away! Don't get me wrong, I wish the region had mountains, but Indiana Dunes has both great forest trails and giant sand dunes you can climb to get a great view of Lake Michigan.
You can do a similar trip to Zion up north which is even easier from the Northside. You can be sleeping in a hammock walking distance to the water in either direction pretty trivially.
I’m less familiar with the western suburbs version but have friends that do starved rock this way.
I don’t think it invalidates your point and the time it takes to get to somewhere “outdoors” is actually my biggest complaint about the area but both of those parks are definitely doable after work… so long as you stay the night.
Here is a link to a group that does those trips as tours and does advocacy: https://www.oofd.org/
I'm a Chicagoan who works for a successful Chicago startup, and I'm planning to leave this year precisely because I strongly disagree with "Chicago is the best city" (at any time of year). There are things that I appreciate about the city (which can be gained from occasional visits rather than residence), but here are some of the things that are driving me out (I'm not sure the extent to which these things have a bearing on its success as a tech hub):
1. There's virtually no nature within a 2 hour drive (you can hardly get past the suburbs in 2 hours after work). There are a few decent state parks (e.g., Starved Rock) that one could do in a day or two, but it's not like Seattle, Denver, or Phoenix where you can be in the mountains in ~40 minutes during rush hour. It seems like Chicago is a great city if you're big into sportsball and clubbing, but for those who want more from life, it leaves a lot to be desired.
2. Chicago has a few charming neighborhoods and the architecture downtown is beautiful, but in general most of the city is kind of ugly (lots of trash blowing around the streets). I particularly hate all of the vomit-yellow brick buildings that plague the north/north-west sides of the city. The more charming neighborhoods are also pretty unaffordable for most Chicagoans.
3. Even with respect to the weather, Chicago is hot and humid from June through August, which makes it pretty unpleasant to be outdoors for most of the day unless you're on the lake (which is invariably crowded). And of course from January through May, Chicago is either cold and bleak or muddy and bleak. If Chicago has a peak time, I would argue that it's September through December.
4. Chicago is deeply politically dysfunctional with respect to fiscal policy, policing, prosecution, etc (and things at the state level aren't much better). I'm happy to pay more in tax to a government that uses that money effectively, but Chicago's taxes are steep and it doesn't seem like that revenue is efficiently used. It's also extremely segregated--when people talk about "Chicago", they're almost always talking about the north side specifically. South and west sides may as well be in different states (if not countries) to most of us north-siders except for the overflow of crime (which admittedly isn't as bad as the news makes it out to be--we're not the worst city in the US for violent crime, we're "merely" the tenth worst of the largest 100 cities).
6. The city lacks any prominent sense of community. Most people don't know their neighbors (although I'm sure there's the odd building or block for which this isn't true). It seems like the overwhelming majority of people are transient and isolated ("alone in a crowded city"). A lot of people seem depressed as a result.
7. Chicago's COL is only low by coastal standards. It's still quite high compared with most of the country. Of course, the present inflation crisis and likely recession are probably going to make these comparisons a bit messier until things reach a steady state.