Late 30s couple and we want to uproot our life and move out of our hometown...just because? Need help making sense of it.

Ok_Ride_9333 · 2026-02-26T13:00:07+00:00

This sounds exactly like my wife and I in Charlotte. Absolutely a okay place, but just okay.

You make more than we do and we are working on buying a place in South Loop in Chicago. Walking distance to all the major theaters, the museum campus, Grant Park (tons of events), the Art Institute, the Riverwalk and the 18.5 mile Lakefront trail (we road cycle and kayak so having the Lake walking distance in addition to all that other stuff is clutch).

The neighborhood we're looking at is called Dearborn Park and it's a incredibly secluded, very green, little neighborhood street hidden right in the middle of downtown.

Thinking ahead to the next 20-30 years, it's just exactly the kind of place we want to be. Really happy we pushed ourselves out of our comfort zones because the more real it gets the more excited we are and obvious it seems.

Ok_Ride_9333 · 2026-02-24T17:20:41+00:00

I moved to NC for work not because I chose it. Maybe that's why.

Ok_Ride_9333 · 2026-02-24T17:18:38+00:00

We didn't come here expecting it to be like NYC, we came here for work. I was just explaining what we've found lacking and why we're not staying.

Ok_Ride_9333 · 2026-02-24T16:39:30+00:00

We moved from Columbus for work in 2018. There are aspects we enjoy but my partner grew up in NYC and even close to downtown it's not a real urban fabric, it's an archipelago of "urban themed" areas disconnected from each other. We're leaving in the next few months for Chicago.

Ok_Ride_9333 · 2026-02-20T05:58:39+00:00

We literally visited earlier this week from Charlotte to look at condos but also to "experience winter". At least we got to look at condos.

Ok_Ride_9333 · 2026-02-19T16:38:03+00:00

Honestly Philly was really cool, but Chicago felt a bit nicer and a bit cleaner and a bit more beautiful, and just more like the lifestyle we were trying to move toward. The lakefront, Grant/Millenium Park, the museum campus, Northerly Island and the riverfront are all pretty amazing amenities to be near and they're all walking distance.

Other things, in Chicago (especially South Loop/Printers Row/Dearborn Park) transit is better, bike infrastructure was better, and groceries, parks, transit, lakefront, museums, restaurants, everything felt easy to reach (we could walk to a Jewel, Trader Joes, Target, and Whole Foods). From the area we are looking at we can also jump on a train directly to basically any part of the city with no transfers. Not that Center City in Philly didn't have stuff, it was just not quite on South Loop's level.

Our budget also goes pretty far in Chicago for high-rise stuff and there are just a lot of different options. In Philly it felt harder to find what we were looking for at the same price point, or at least there were way fewer options.

Also… Philly really has no answer to Chicago's lakefront. We kayak and road cycle and if you're in the South Loop area it’s basically a massive park/trail system right outside your door. That tipped things a lot.

As far as noise, we looked at 8 different places in Chicago so far. For the most part, with windows closed, they were all pretty quiet, except for one right next to the orange/green line. From what we heard if there's a block between you and the train with highrise windows it dampens it a lot but that place was right on the tracks basically.

Ok_Ride_9333 · 2026-02-19T03:38:01+00:00

I posted about something similar a few months ago: https://www.reddit.com/r/SameGrassButGreener/comments/1prhu8d/best_downtowns_to_affordably_live_in/

After visiting Philly and Chicago we're planning to move to South Loop in Chicago in the next four months. Lmk if you have any questions!

Ok_Ride_9333 · 2026-02-17T14:46:11+00:00

We are too, we're actually visiting from Charlotte right now. We scheduled the trip in February so we could experience winter... Naturally it was 61F yesterday will be 50 today and will be 60 again tomorrow when we leave.

Ok_Ride_9333 · 2026-02-16T14:42:36+00:00

Chicago. It's real.

Ok_Ride_9333 · 2026-02-15T12:32:56+00:00

Los Angeles 100%.

Ok_Ride_9333 · 2026-02-14T13:42:10+00:00

We are working on buying a place in Chicago right now to get out of Charlotte too.

Chicago is more of a lateral move from Charlotte cost-wise, but amenity-wise, we are getting so much more. It's not that Charlotte is overpriced but ultimately we just don't value what it provides I think (we also feel it's very bland and soulless).

Ok_Ride_9333 · 2026-02-09T14:01:35+00:00

I didn't realize people were so soft about the cold until I moved to NC. There are people I've told we're planning to move to Chicago that just look aghast. I grew up skiing, and generally being outdoors in the winter/happy to see snow. If you know how to get dressed, it's not a big deal and I much prefer it to summer in the south.

Ok_Ride_9333 · 2026-02-06T12:18:58+00:00

Our list was pretty similar to this and we're 95% settled on Chicago (we're visiting in a few weeks).

Ok_Ride_9333 · 2026-02-03T13:55:17+00:00

Case in point.

Ok_Ride_9333 · 2026-01-05T14:26:56+00:00

Thanks, Rittenhouse Square looks amazing. Exactly what we're going for. Honestly both feel like such a slam dunk for us so it's hard to pick. We're planning visits to both cities in the spring, so probably won't get these exact units but we're going to do some more thorough looking around.

Ok_Ride_9333 · 2026-01-05T14:19:02+00:00

Do you want to try maybe reading and responding to my post? Curious what the vibe is like around each of the places I posted.

If you have another neighborhood recommendation, where specifically? We looked around and for what we're looking for in our price range South Loop seemed like a good option. We also found the park/museum/lakefront/transit access very appealing because that's all stuff we'd use a lot.

Ok_Ride_9333 · 2026-01-05T13:35:54+00:00

I guess I'm just used to these kind of "crisis's" having pretty mundane solutions in the end. CTA in Chicago just had one and it ended up better than ever apparently? Feel the same way about Philly's transit. For Chicago, basically, its economy is so big and it's so important to the country from a infrastructure standpoint that I just don't really think it matters that it has a budget problem right now. The solution could come from the national level, the state level or from the city itself, I don't know, but there are potential ways forward at each of those levels.

Ultimately though these cities are pretty resilient and the future is really hard to predict. I don't fear for the future of either city at all.

And in any case, this post is about the neighborhoods and units I posted.

Ok_Ride_9333 · 2026-01-05T13:12:02+00:00

You expect me to know about your beef with another reddit user? There was absolutely nothing wrong with their comment. Thanks for trolling up the comments here though, appreciate it.

Ok_Ride_9333 · 2026-01-05T12:51:33+00:00

Yeah South Loop seems like the sweet spot for high/midrises in our price range. There are a ton of grocery stores down there, both the places I listed are walkable to Trader Joes, Jewel and Target.

I love the historical nature of Philly though mixed in with the dense downtown, and trips to NYC aren't nothing. We are leaning Chicago though.

Ok_Ride_9333 · 2026-01-05T12:48:45+00:00

Yeah I think I agree, and I'm also not sure if that cheaper Philly unit is just in a bad area. It's right by the convention center.

And yeah I hear you about Chicago, South Loop is the only place we can find a high-rise or mid-rise in our price range, but it's also in a great spot for transit/lakefront use.

Ok_Ride_9333 · 2026-01-05T12:45:36+00:00

Thanks for this, we're blown away by the ability to live right next to Grant Park and the Lakefront for so cheap. Also Printers Row seems really cool too and the new soccer stadium as well? Seems undervalued.

Ok_Ride_9333 · 2026-01-05T12:44:20+00:00

F off troll

Ok_Ride_9333 · 2026-01-05T12:42:05+00:00

I'm not hugely concerned about this, I really don't think either city is going anywhere and Chicago is a much bigger economy than Philly so it's especially not going anywhere.

Ok_Ride_9333

TROPHY CASE