Toronto vs Chicago
They are both situated on the Great Lakes. Is the investment banking scene comparable? since they are both behind nyc in terms of deal flow.
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A bump
Bump
Probably Chicago > cause you get paid in USD and relative COL is probably lower
Chicago has a much bigger buyside scene while Toronto probably has better / more consequential banking offices (for BBs at least. I think Chicago is better if you want MM).
Isn’t onex a big buy side shop in Toronto?
yes but also basically the only mf shop in toronto
and the entirety of Canada even
Buyside in toronto is small af you got onex and brookfield with the rest not comparable to chicago
Chicago
Chicago for PE, Toronto for not making a wrong turn into the wrong neighborhood and getting shot.
The 2 cities do share some similarities (on the great lakes, very spread out), but Toronto is Canada's finance capital while Chicago is a regional hub. From a banking point of view, Toronto sees a lot more dealflow since it's where 80%+ of Canadian bankers are. Living is night and days, Toronto's comp is lower to significantly lower, taxes are higher and cost of living is through the roof, Toronto is one of the most overpriced cities in the world. Chicago is an absolute bargain compared.
I grew up in Toronto and have spent some time in Chicago for work and they are indeed similar in some ways. I love Chicago, and have seriously considered moving there full time in the past
Similar population size, topography/green spaces mixed with urban, weather, both have notable Mies van der Rohe building complexes (although Toronto's architecture is terrible compared to Chicago). Both have awesome neighbourhoods that are more affordable to live than New York (Lakeview, Old town, Gold Coast in CHI, Annex, King West, Yorkville, High Park etc in Toronto) . Both cities generally have a more chill/laid-back vibe than NY, which can be both a pro and a con. Toronto has more ethnic diversity and draws professionals from all over Canada (and somewhat globally). I found that the people who end up in Chicago generally have some sort of family/personal ties to the midwest. Toronto also has a wider range of dining options, but Chicago has a much better high-end/fine dining situation (not just Alinea/Next)
From a professional standpoint, I echo what the other posters above said. Toronto is Canada's financial hub and a global hub for select industries like mining You encounter a wider and more diverse range of sectors (natural resources, FIG, C&R, TMT, real estate, industrials etc) in Toronto. Chicago is somewhat of a key "regional" hub for the Midwest and is predominately industrials focused, with some C&R, food, packaging, RX, ed tech etc.
The banking scene is larger in Toronto (the big-6 canadian banks are HQed there and all of the BBs and EBs have offices, but are smaller than Chicago on average). The MM banks of Chicago (Blair, Baird etc) are probably sized similarly to some of the smaller Canadian banks like Canaccord Genuity or GMP. A lot of bankers can bank Chicago/the Midwest from NY/SF, but Canadian companies generally prefer a local face (suitcase banking from NY has a mixed track record in Canada)
Buyside is better and deeper in Chicago. There are more PE firms , including a bunch of very credible UMM firms like MDP and GTCR. The HF/AM world is also way better with big players like citadel and a bunch of quant funds (e.g. DRW). In Toronto, only Onex can compare in PE (although Altas Partners is on the upswing) and most buyside positions are with the pension funds which unfortunately do not pay well and some have questionable middle/senior management. HF world is much less developed with only a few credible funds
Thanks for this, very helpful post. Agree on Chicago's strong buyside (also believe Thoma Bravo is based in Chicago). Re Toronto, i assume Brookfield is a big presence since they're headquartered there? How do big Canadian pensions (like CPPIB, OTPP, and HOOPP) compare to big US pensions (like Calpers, TRS and OPERS)? Are the Canadian pensions comparable with the US counterparts in terms of sophistication, access to top managers, etc.? (Curious about this given your point on questionable middle/senior management.)
Stopping by to affirm the greatness which is Chicago. Extremely happy with my decision to move to the city.
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