I think it is risky, but you already know this or you wouldn't have asked the question. How big a risk it is depends on a couple of things that you didn't mention.
The most important issue in my mind is how long you've been dating the guy and how well you feel like you know him. If you two have been together a while--a year at the very least--then you probably have a pretty good idea of what he's about, and moving with him is a calculated risk. If you've only been with guy a few months or less, then I think you're taking a big chance to go to a new city with him. You just don't know the guy well enough, and the odds are greater that he might dump you out of the blue or do something to make you want to dump him. Then you're stuck in a strange city and you've just lost the one and only friend you had there: him. Oh, and the city is his turf, so you'll feel likely even more out of place after you break up.
That leads me to my next question: how independent are you? If you move for this guy and you two break up, will you be lost and lonely in a new place with no friends or family? Or will you welcome the challenge of making your own way in a new city, finding your niche, making new friends and taking Chicago by the balls?
No one wants to think about breaking up with their mate, but if you move for him, you have to consider the worst-case scenario, which is you alone in a big strange city. If you plan on living with him, then the scenario also includes you suddenly having to find new living arrangements, which will suck.
These are the questions I would be asking myself before moving to a new place with a partner. Some will say you should never move for a guy (or a girl), but I don't agree with that. Love requires taking risks and trying new things, and people follow girlfriends and boyfriends all the time. Sometimes it works out, sometimes it doesn't. The key is to be sure you know him--and yourself--well enough to make it an educated risk, not just a whim. Otherwise, I wouldn't do it.
Good luck. Thanks for the question.
Are you living together now? Do you think about marrying him one day? If it’s a serious relationship like you said, has HE talked about marriage? Living with a guy is not a stepping stone to marriage. It doesn’t hurry the process; it puts it on the back burner. Does distant make the heart grow fonder? Sometimes. Just some things you might want to consider as well.
I have moved to new cities a few times (and in different countries, actually haha) and independence can be a huge issue! In addition to the after-effects of a possible breakup, it's hard to move to a new place and make your own friends to begin with, but it can be a big strain on a relationship if you've only got each other for a while. I've known several couples who broke up for that very reason.
Something that worries me a bit personally, as I'm moving from Canada to the UK in the fall for my boyfriend, but we'll see how that goes, haha.
You also would always have the option of returning home if it didn't work out, wouldn't you? I once considered moving out of the continental US for a guy, and had a back up plan in case it didn't work out, for how I would get home again. I decided not to move (just visit often), but we are planning our wedding for next spring! =) Then I will be moving in with him. Long distance dating can work, if you're both dedicated to the relationship and willing to put in extra effort.
Let him move back and in 3 months if he still wants you to move then take the leap.
I was, quite literally, in your situation. I was with my boyfriend all throughout college. We graduated; he went home to Chicago and I did my master's program overseas. I moved to Chicago when I finished my program instead of going back home.
I'm still in Chicago, but we are not together. We broke up 3 months ago. The worst case scenario did happen for me. I had to find another place to live and be able to support myself. It's been a struggle, but so far, so good.
It's a risk moving for someone, but I've met so many wonderful people and had great experiences with and without my ex.
Chicago is a neat place. Move for the adventure and the possibility of something new, but understand that it may not work out exactly the way you expect.
I think Layla has good advice. See how separation goes--if with physical distance, either of you experiences a fading of enthusiasm for you moving with him, that's a huge red flag. That's not to say that you should approach the separation expecting to grow apart--not by any means! But tread carefully, check out Chicago for your contingency plans, and make sure you won't regret your choice.
Breaking up, even if you move, isn't going to crash your life, either. Chicago's an incredible place and there are plenty of opportunities for you to forge your own way. And there's nothing tying you there.
I hope it works out for the two of you!
I've been in a long distance relationship with my boyfriend for almost 3 years, and although we saw each other almost every weekend, he wanted me to move to his city (we are from the same hometown and he didn't want to move there because of his job, and I was able to make the transition easier). I always have said that I would never move anywhere for a guy, but I did just a few weeks ago. We aren't living together, but we live in the same apartment complex.
I must say it's a HUGE transition. I feel completely out of place. I don't have a lot of friends here, except his, and we are already treading on thin water because I'm accustomed to having my own sense of independence at times. I'm not used to him always being around. I know I should want that, but now that he is, I feel myself feeling smothered. I wish I had my own friends etc., to help me establish myself here too. Everyone needs a break sometimes. I don't think to be a happy couple, you have to have every meal together, and do EVERYTHING together. I didn't expect to feel this way. I hope things all work out. I guess it takes time getting used to everything. At least I'll figure out if we will be good together forever! My honest opinion though is that moving for another person (unless there is plans for marriage in place etc) is a horrible idea. Every situation is different, and all couples are different. I don't know if I'm in the minority or not when it comes to how I'm feeling right now.