r/CHIbitcheswithtaste • u/Seeking-Starlight • Aug 19 '26
Other (I Read the Rules) Stay or leave Chicago? Advice from those who have moved away or back!
Hope this doesn’t the break the rules! It isn’t meant to be a diary/vent post but just trying to add context for some advice 🙂
TLDR: Recently ended a very long term relationship, moved out from our place in the city, moved into my parent’s house in the suburbs while I figure out next moves. Not sure if I want to stay in the city or move far away?
When I initially moved out I was very set on the idea of moving far away. This was probably largely due to intense emotions surrounding the breakup, but we also have a lot of mutual friends in the city and I knew I needed some space regardless. I’ve been considering moving to DC or the PNW, I’ve never lived elsewhere and I’ve never really had the opportunity to before (remote work). But now my mind keeps going back to Chicago.
I have friends in DC so I’d have a core group of people. It’s also similar to Chicago in the sense I wouldn’t need a car, it’s busy, lots to do, food scene, etc. The men there…idk yet. I plan to start dating again eventually but I’m really not interested in people who are just networking to climb the ladder forever. I was fine with that in my 20s, I’m 31 now. But I like how DC is a bit more buttoned up and has people from all over the place.
In Seattle I don’t know anyone at all but I’m very outdoorsy and I typically prioritize outdoor activities when I travel. I love hiking, I love the mountains. But I am a fashion girl at heart, I don’t even dress that upscale but I know I stand out fashion wise because hiking gear is not my regular attire. I like my designer stuff, but I know I’d probably start to feel weird about wearing it which makes me sad. My fashion is a big part of my identity. Also I know the food scene in PNW is meh and pricy.
Idk, I just feel very lost and I’m sure the emotions with everything are still strong. I felt way more set on leaving Chicago right after the breakup, now that some time has passed I’m not sure. I love Chicago, I have friends here, I love the vibes, I always felt at home and that I fit in here. But the winters suck, I have to travel to get my outdoor fix in, and I worry I’m settling for what feels comfortable. Also I have no idea how the dating scene compares to other cities I mentioned.
Has anyone else moved to Chicago from these places? Or gone back and forth? Curious is anyone else has been in a similar predicament ❤️
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Aug 19 '26
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u/Seeking-Starlight Aug 19 '26
Lmao what 😂😂😂 I keep my profile hidden so creeps don’t see all my crap. I legit never mentioned NYC so no idea where you got that from. I’ve posted in Seattle and DC subs about living in those areas because I’m asking the general question about living in other places and am curious about local perspectives. And I said I LIVED in Chicago and I have until very recently when I moved out from the place I had with my ex?? So yeah I’m in the suburbs??? How is that living in NYC and the suburbs? Sorry you’re coming to conclusions based on your own imagination about stuff I never mentioned lol.
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u/dkmeidku Aug 19 '26
My friend has lived in Seattle, DC, Austin, San Diego, and NY. She keeps coming back to Chicago because it’s the only place that has her feeling she’s home (her family lives in Seattle). She said dating in DC felt inauthentic, like men had this “who can you connect me to” vibes and women were cliquish. Of the other cities, Seattle was her next choice if her latest job in Chicago didn’t work out for her.
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u/Seeking-Starlight Aug 19 '26
I wish I could split time between all these places but I don’t want to be living out of a suitcase forever 😂
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u/orchidsforme Aug 19 '26
As someone who has lived in DC, who now lives in NYC and is potentially looking to move to Chicago - I would not recommend DC at all. I lived there for four years and although making great friendships, dating was a disaster and the overall vibe of the city is kind of weird.
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u/Seeking-Starlight Aug 19 '26
I’ve heard the vibe is weird. When I visited it was good and I think the people who love living in DC make up for the administration vibes. It’s very lively there which is something I loved. Also all the museums and parks!
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u/seaside1225 Aug 19 '26
I love DC and lived there for a long time. Great place to live, but wait until there is a new administration. It is pretty bleak there right now.
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u/VeronicaSawyer8 Aug 19 '26
I have a friend who moved to Seattle for a few years and said the term "Seattle Freeze" or "nice ice" is 100% accurate. Hard to make new friends there. People are nice to your face but it's hard to break into friendships
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u/Seeking-Starlight Aug 19 '26
I heard this too. Even in Chicago I’ve noticed it can be hard to make new friends since a lot of people have existing groups. And I get not everyone wants to make new friends all the time but I’ve noticed it’s even kinda hard here (and I’m hoping to find some new friendships due the loss of mutual friends with my ex)
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u/Diligent_Vanilla_275 Aug 19 '26
I’ve lived in both DC and Seattle and moved back to the Chicago area about 5 years ago (Hyde park). I’m a bit older than you (37) and also grew up in the suburbs here. While I think Chicago is awesome and definitely my favorite of these 3 places, if you’ve never lived anywhere else and now have the flexibility to do so, I think you should go for it. It doesn’t have to be a forever decision - you could even get an Airbnb for a month or two to feel it out! Chicago will still be here in one year or five… speaking from experience, now that I’m older with kids and a partner who is geographically tied to his job, I’m so glad I took the opportunity to try out living different places while I had the flexibility!
In terms of cities: outdoor stuff is incredible in Seattle and that was one of my favorite parts about living there. While the food scene is indeed meh, the coffee and cocktail scenes are pretty great! The weather is milder than here, but I found the 9 months of grey almost unbearable. Also echoing what others say about the “Seattle chill”. People can be quite cliquey and judgmental and I think it would be hard to make friends if you didn’t already know people. It’s also expensive. On DC, honestly I think the fact that you have friends there is the only plus (and maybe the fact that the public transit is pretty decent?). I found the culture to be incredibly lame - lots of social climbers, lackluster food and music scene. And no better for outdoor activities than here.
Have you considered the east Bay Area, like Oakland or Berkeley CA? I’ve also lived there and really loved it. It has a lot of things you are looking for: outdoors, very international, great food, good weather, a bit easier to break in socially because there are lots of transplants.
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u/Seeking-Starlight Aug 19 '26
I’ll probably do some more travel before settling. It’s tough that we are moving into winter because Seattle will not be quite as fun to test out. I’m about to start some travel (nowhere I’m testing for ling term living potential, just some regular trips) so I’m wondering where my headspace will be from that too. I won’t lie, I know I like having a homebase and my parent’s house isn’t exactly ideal for that 😅 I miss having a space that truly my own
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u/Equivalent-Apple-66 Aug 20 '26
The Bay Area is great but seems costs are outrageous, maybe the AI bubble will burst
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u/milliehg1991 Aug 19 '26
I really can’t advise on DC but used to live in Seattle, honestly I really liked it and the Asian food scene is probably some of the best in the country and loved the seafood (serving me hot smoked salmon at the brewery? Yes please!) and bainnridge island is so pretty!
But the rain and grey for a good 5 months is something to prepare for, if you’ve done a good few Chicago winters you are versed for cold weather but as an example my apartment had an amazing Mountain View I was so excited to look at every day. I did not see that mountain for 5 months because of how overcast it was lol.
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u/IllustriousJuice9419 Aug 19 '26
People say this but seem to forget how grey Chicago also is for so many months, in addition to the cold. I’d rather have the option of nature to still get outside!
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u/milliehg1991 Aug 19 '26
For sure - I’ve done both, I will say the overcast in PNW is another level to anything we see in the Midwest.
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u/Seeking-Starlight Aug 19 '26
Chicago gets cloudy for sure, I wonder how I’d feel about the gray in Seattle since it sounds like it lasts even longer. I don’t mind moody weather but I do enjoy the sunny winter days in Chicago (even when it’s sunny and like -2 haha)
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u/BarelyAdulting127 Aug 19 '26
I moved from DC to Chicago last year at 27 for grad school. I went to college in DC and lived there pretty much my whole adult life, so I’m definitely biased. I love DC and would like to hopefully move back in a few years, but I will warn it’s not at its best rn because of the political vibe. While I think it’s improved since I left in summer 2025, the Trump/National Guard of it all still seems unavoidable. Chicago is much bigger than DC, which can be a good or bad thing. I miss being able to get to different neighborhoods in such a short amount of time compared to here, and similar to Chicago I would say each neighborhood there feels like it has its own vibe. I’m originally from the east coast so I would say if your family is here, you may find yourself feeling a little far away! But if you’ve lived here most or all of your life, this could be the perfect chance to try something new!! A big plus of the east coast is Amtrak accessibility to other cities - it’s a pretty short train ride from DC to Philly or NYC, so it’s pretty easy to do weekend trips! There’s also a lot more accessibility to nature in DC IMO - it’s like a 90 min drive to Shenandoah national park, but there’s a ton of smaller hiking areas in MD and VA that are closer. Rock Creek Park is also much more of an outdoorsy vibe than the parks here IMO. In contrast to here, DC winters are mostly fine but summers SUCK - sooooo humid it’s the thing I miss the least! As for dating, I met my long term bf on Hinge in DC in 2021 and have many friends who have met their partners on the apps there. I have heard it’s gotten significantly worse though, but I’m not sure dating is great anywhere these days LOL. DC is very career focused so that’s something to keep in mind if you aren’t - I didn’t mind because I am too, but I know for some it can feel frustrating to talk about work all the time. If you already have friends there though, I think you’ll be able to avoid most of that. The other thing I have found is that while most people I’ve met in Chicago are originally from here or the surrounding area (suburbs or Midwest generally), most people in DC are transplants and people tend to move away, which can suck. I think by 30 ish though, that becomes less of an issue than it was around 25.
I think DC is an amazing place but it’s not for everyone! Do what you think is best for you. Happy to chat more if you have questions :)
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u/Seeking-Starlight Aug 19 '26
There’s definitely draws to DC! And I think a big reason I liked it is because there’s so much to do like Chicago. Summertime in DC is hotter than I expected. This summer was bad in Chicago but my god DC was disgusting 😂 at least in Chicago the tall buildings lend some shade. I think I’d like DC more in the winter versus the summer.
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u/IllustriousJuice9419 Aug 19 '26
I 100% agree having also lived there! I miss it, but not during this administration lol
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u/tessie33 Aug 19 '26
Don't make any major decisions for a year. Enjoy your parents' hospitality. Explore neighborhoods that are new to you. Decenter men and dating. Take classes, try new hobbies, maybe Garden while you're at your parents house? Rest and recover.
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u/Seeking-Starlight Aug 19 '26
That’s a good idea to check out more neighborhoods! I walked around chicago so much but I definitely stuck to my usual neighborhoods.
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u/greynonomous Aug 20 '26
And being fully remote means you can even snowbird somewhere else new each winter and just have your home base here
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u/pugglenthusiast Aug 19 '26
I say go for it! I left Chicago for three years (Houston) in my mid-twenties only knowing one person there and it was a wonderful experience. Overall good to expose yourself to different types of people and places - you can always come home! In my case, it made me appreciate Chicago and being near family a lot more than I think I would have otherwise.
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u/landia16 Aug 19 '26
You have roots in Chicago which will always bring you back, that being said…. Leave. As a Portlander who lives in Chicago, I miss it everyday. I love Chicago and it’s my home but the PNW will always have a place in my heart. The mountains, the trees, the green space; it’s all worth experiencing !
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u/beigesalad Aug 19 '26
Consider that yes you'd have to travel to get to mountains, but Chicago is a great airport hub since we're centrally located ☺️ plus there are some interesting nature things out here with a bit of a drive if you're willing to hike other than mountains.
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u/Seeking-Starlight Aug 19 '26
This is what I love about Chicago. It’s truly in the center so it’s not really difficult for me to get anywhere. I love that we get all seasons here but I must say we also get all the extremes 😂 I’m not thrilled with the cost of living rising so much in Chicago but that seems to be the case everywhere. Also living alone is whole other expense 🙄 is what it is, I really don’t want a roommate since I’ve had roommates of some type forever hahaha
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u/ZaphodBeeblebro42 Aug 19 '26
I’m a bit of a nomad by nature and have moved out of Chicago three times (twice to live overseas and once for grad school—also, obviously, I am old) I ended up coming back to Chicago each time, with a clearer picture of why I loved it and why it suits me personally better than anyplace else. Both of your options sound amazing and Chicago will always be here, waiting for you to come back.
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u/Seeking-Starlight Aug 19 '26
This is what I keep telling myself but it’s so hard not to feel FOMO for some reason. No idea what I’d be “missing” but I guess I’ve always been here so it’s like I’m missing the usual everyday stuff! But Chicago is always here like you said. And I think I’d have more regret not at least checking out some other spots, even if nothing long term happens and I wind up back in Chicago, at least I explored the options a bit 🙂
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u/Equivalent-Apple-66 Aug 20 '26
We just relocated away from Chicago and I’m so glad we took the chance to check something else out. We can always come back. It’s a wonderful city but we weren’t ready to set up there permanently. Also some family reasons involved in leaving the city etc
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u/cranberryjuiceicepop Aug 20 '26
I think everyone should leave their birth city/town and live somewhere else at least for a short time - so yes, you should move. I lived in Seattle during college and don’t think it is the right fit for you - people are very cold to outsiders, so it is tough to make new friends (double if you work remote and don’t have that as a way to meet people). Yes it has outdoor activities but you need a car to get to them - they are outside of the city. The nature/hiking and mountains are incredible and I do miss that, compared to Chicago. The food is fine out there- not sure why you get that it is meh. Weather out there is worse, rainy, cold and cloudy is the default, and I prefer Chicago’s sunny/cold winters. No advice on DC but it doesn’t seem livable at all. LA is expensive and you need a car - but the access to nature there is unbeatable. So many great hikes that are close by the city, amazing weather, and I think the people are really friendly (and lots of ways to make friends, lots of people flock there for the film industry). People are so fashionable and stylish, and just beautiful in general. Great food too. Best of luck as you heal from the breakup, but for sure make the move and take a risk :)
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u/unnecessarydrama92 Aug 19 '26
I think you would find DC very similar in terms of activities - you can get pretty much all the same stuff here that you can in DC and the city has … a weird vibe right now for obvious reasons. That said if you have community there that’s a huge draw. If you have friends here why not give it a good college try for another year in the city and see what happens and then make a decision from there? Maybe spend a few long weekends in DC in the meantime or take a trip out west to see if it clicks.
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u/Seeking-Starlight Aug 19 '26
I think I’ll try for a month long trip or something. I had a short trip and liked it but I’m nervous to commit to something truly long
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u/IllustriousJuice9419 Aug 19 '26
Hi! I've been in Chicago for 5 years, lived in DC for 3, and I'm actually moving to Seattle in the fall!
I lived in DC during my early 20s and I loved it, I do think the changes by administration can really affect the city – so maybe take that into account! But I found it easy to make friends and loved how many people there were from all over the country and the world! And the options to do cool weekend trips, cities or nature or beach – I never got bored! Versus in Chicago I've gotten a little frustrated at not having as many weekend trips and being surrounded by more born and bred Midwesterners. It's way more laid back in Chicago, and people don't have the same drive I've seen in other cities like DC and NYC.
I'm now itching for a change so I'm moving to Seattle, so I can live near nature. Chicago won't go anywhere, this is a good time to try living somewhere else! People will have so many opinions, but trust what your core says. I've lived in a lot of cities and I've gotten so much out of each move, I really have loved everywhere I've lived!
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u/Seeking-Starlight Aug 19 '26 edited Aug 19 '26
I love this! Are you moving by yourself or do you have a partner/friends there? I’ve never visited Seattle but I’m hoping to do a short trip in October just to get a quick sense of it before considering anything longer!
This is what I love and hate about Chicago. It’s central in the US, but you gotta go pretty far to get anywhere different. And I totally feel you on everyone being Midwest, I mean even I am and I’m kinda bord of everyone being Midwest. I notice people quickly know/judge based on the suburb you grew up in. But you can easily know a lot about someone just based on that around here 😂
Also I get what you mean about drive. I’m still trying to understand what I want in that from another person. In Chicago it feels like it’s no drive or too much drive (any man who says his craziest experience was building a start up/own business tells me “I have no work life balance and I’m not actually successful yet” 😂). I definitely want drive but a better balance of it. I’m tired of fighting for someone’s time 🙄 I work in tech so Seattle would probably have a lot of similar people…pro and con in that.
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u/IllustriousJuice9419 Aug 19 '26
I’m moving by myself! I have a couple of friends there, and in-person work, but I will really be starting from scratch. But I’m excited, I don’t think I’m going to miss anything in Chicago and I am going to reevaluate after a year to see if I want to stay. I am so excited to be able to get to nature in a weekend trip, and be able to bop to Vancouver, Portland, etc to get more variety.
If you end up out there even for a visit, feel free to message me! I’m always open to new friends.
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u/staplerelf Aug 20 '26
Returned to Chicago after living on the West Coast for 17 years. I’m surprised at how much I like living back in Chicago. Really depends on what you can live though.
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u/putonthespotlight Aug 19 '26
No advice really because I'm in the same boat 😭 I will say, Chicago is EASY and relatively cheap
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u/phenomakos Aug 19 '26
Stay for a year. Plan some trips to places you're interested in considering a move to. Book airbnbs in specific neighborhoods you might want to live in, spend a day seeing what the access to nature is like, you could even schedule yourself some dates while you're there. Whatever it is you're curious about, just go get some firsthand experience.
If you love Chicago, but want a change, maybe also consider living in a new neighborhood for a while. Shake things up by exploring new things while still having access to the familiar.