Hi all,
My wife is a US citizen and we will be moving out to the US next year from London. I currently work for a major brokerage (JLL/CBRE) in an IS/Capital Markets role in London but focused on opportunities across the continent, not just UK.
Appreciate NYC is the best and biggest city for RE careers, but for personal reasons the city isn’t for us. We’ve identified Chicago and San Francisco as two cities we’d love to live in. From a career perspective, which of these cities is stronger and offers a broader range of opportunities in the industry? I’m still relatively junior and unsure where I want to end up, but like many people in Brokerage I have the principal side in mind.
As I understand it Chicago has a more diversified economy than SF, but not sure it necessarily means it’s better from a RE career perspective. Appreciate it’s hard to say without specific career plans (working on these) but curious to hear people’s general thoughts on the differences and potential opportunities in these cities.
Thanks all in advance!
Chicago offers diverse opportunities due to its varied economy—industrial, office, multifamily, and development sectors are robust. It’s great for building a broad foundation in RE.
SF leans tech-heavy, with opportunities in office and multifamily catering to that sector. It’s competitive but offers strong growth for those interested in working with cutting-edge markets or tech-driven projects.
If you're leaning toward principal-side roles, Chicago's affordability and access to institutional networks might be advantageous. On the other hand, SF’s investor-driven environment could align well with capital markets aspirations.
Either way, your brokerage experience in London will stand out in both markets. It might also help to look into networking events or firms that span both cities. Best of luck!
Thanks mate, this is a really balanced and helpful response. Sounds like both cities can offer a lot, but Chicago wins on breadth and diversity here (and that definitely appeals to me given the job hunt will be a bit of an unknown coming from London)
I think Chicago has more CRE opportunities since it basically commands the entire north-midwest region, whereas SF splits CRE opportunities with LA / OC. That said, each have plenty and it might help to say what type of role and real estate you're interested in, and why these two cities are the ones that made your short list. These cities are very different in almost all forms - culture, climate, geography, economies, etc.
Appreciate this isn’t helpful but as for career path, I am pretty open. My current role is fairly logistics heavy but focuses on large portfolio/platform level transactions (mostly upwards of €100m). I haven’t been in the role for too long but wouldn’t be opposed to principal or brokerage side roles in equity or debt. Somewhere with strong deal flow is most important to me.
As for reasoning as why we’ve landed on SF/Chicago, roughly a case of NYC being similar to London (expensive, overcrowded) and LA being too hot and perhaps a bit pretentious (this is mostly anecdotal). Aware SF is also expensive as hell but I think the access to nature would make up for this.
DC and Boston are in the conversation but worry firms there would be too small/localised and would be a bit of step down from the large pan-European deals I’m working on now? Not sure if this is a valid concern though!
Those types of roles can be found in either market. I could be wrong, but aside from NYC I tend to think LA has the largest CRE in the country so you may want to reconsider it.
As to your choice of city, LA really isn't that hot, especially if you live on the west side (closer to the water, the cooler it gets. 90% of the year you don't even need air conditioning if you live in Santa Monica or similar spot). Pretentious vibe in LA is mostly Hollywood driven (not that it isn't found everywhere, but for example the real estate crowd in LA isn't any more pretentious than any other big city). I speak from experience as someone that grew up in Chicago and worked CRE in LA that I have met so many great people in CRE in LA that aren't pretentious whatsoever (to be honest now that I think about it, they're almost less pretentious than in Chicago for some odd reason. I think the type of people that are attracted to CRE and SoCal lifestyle just mostly tend to be down to earth people whereas the ones in Chicago tend to be more of the one's driven to that big city, finance-y vibe. But we're splitting hairs here. By no means am I labeling the Chicago crew as pretentious people.).
If you pick the large gateway markets (NYC, LA, SF, Chicago), I honestly think you picked the most opposites amongst the bunch. If you're coming from London, you'll be used to the grey Chicago winters, but you mentioned access to nature in SF as a big reason you like it which is why I bring up that Chicago is the opposite aside from a few months during summer when you can hit the lake or take a ride up to Wisconsin (which doesn't compare to California nature by any means).
Both are good enough from a real estate career standpoint, but as others have said, Chicago will have a much deeper / broader pool of options for you.
Lifestyle-wise, they are drastically different and that should probably be what you make your decision on. Chicago is a city....very dense, tons of neighborhoods, diversity, a million restaurants, big nightlight scene, no shortage of theatres/museums/sports, etc. Summer and fall are amazing, winter you have to get through, spring sucks until you hit May. Comp is strong and cost of living is downright cheap compared to NYC/LA/SF. I have to imagine coming from London you are going to be floored with what you get for the money.
SF...you can surf and go skiing in the same day. It's a stunning landscape. Hiking everywhere. Napa/Sonoma is a short drive away. Chicago can't come close to the natural attractions you get in SF. Weather is pretty consistent - I love SF's weather. The tech industry has driven a culture there where it's hard not to be ambitious. Seems like everyone is trying to create something. That can be a really intoxicating environment for the right person. The city itself is smaller. Will feel miles apart from what you get in London/Chicago/NYC in terms of size. Good restaurant scene...nightlife is pretty terrible. The city is dirtier than Chicago and can be a bit exhausting - homelessness/petty crime is something you have to deal with on a daily basis. It's expensive. You and your wife have to be making $300K/yr to feel like you are doing okay - and okay doesn't mean owning a home, it means renting a niceish apartment.
What your wife does for a living will also impact this, obviously.
Thanks mate, this is a super helpful overview of these cities! Chicago sounds more up my street from what you’re described here - and cost is huge factor (especially coming from London, the idea of having my money go further in Chicago is very appealing).
Curious what you make of DC or Boston compared to these cities? Perhaps a step down career wise but might offer other lifestyle benefits?
My gut is that Boston and DC are probably similar to, if not a step above, SF for real estate options. Boston you'll get a little more life science, DC is obviously government. I love both cities but have never lived in either. Both are higher COL areas. I don't know if you are looking to go to Europe on a regular basis but Boston would be great for that.
Can't go wrong with any of the four cities you are looking at. Do any of the four work better for your wife?
Agree, except that SF almost certainly has better food than chicago. Probably the best food city in the US per capita, only NYC is better in terms of restaurant diversity and absolute options because of population size. And in terms of 3 and 2 star michelin, SF wins hands down.
They are different. Chicago just has more of everything. SF is better at the top, but I really miss the sheer quantity of great spots in Chicago.
Same here, was very worried to work in SF till I actually visited. The homeless situation is definitely far worse in LA (don’t know about Chicago), in SF it’s really just restricted to the tenderloin for the most part with tiny pockets scattered throughout the city. Weather’s much nicer than Chicago and also really like the fact that SF is so close to the ocean.
My understanding from people I know who have lived in both is that SF has a much much worse homelessness and petty crime problem than Chicago, and SF is far more expensive. That said, if OP likes summer more than winter, or beaches (although Chicago does have beaches but not in the same way), or works in tech, then SF is better.
Would you say the higher pay in SF has actually equated to a higher QOL given the higher living cost, or whether it’s absorbed by higher rent? Not the first time I’ve heard Chicago comp is lower but not sure if the higher number of opportunities and lower COL make it a better option?
Have no dog in this fight but also considering personal lifestyle there is something to be said for the living costs in Chicago being substantially cheaper than NYC/SF/LDN/etc and the enhanced lifestyle that brings (if you can deal with the winters)
Can 100% deal with the winters. Having experienced both (albeit the Northern US winter for a much shorter period of time), there is nothing more oppressive than the London gloom (we get approx. 35 clear days a year, I wish I was joking…)
Chicago COL and higher purchasing power relative to cities like London SF/London is a real pull.
Curious if anyone has any thoughts on Boston or DC in terms of solid firms and opportunities to work on deals nationally? Again conscious that most of these will be in NYC but trying to gauge where else offers these sorts of opportunities
In my experience, NYC and LA are the markets doing a lot nationally (or even internationally). SF and Chicago too but I think you'll find more in SF / Chicago focused on the region they're in (SF = west coast, pacific NW, Chicago = midwest). Boston, DC, Dallas, Houston will be a lot heavier on just regional and not nationally. Exceptions everywhere. There are firms in random cities like Minneapolis doing deals nationally.
Yeah this. Every major city will have firms doing deals nationally. Some cities will have five and some cities will have 500, but every market has a few.
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