Know of 2 or 3 now-34yo guys (Wharton undergrads) who chose to go to Chicago as first-yr IB M&A analysts back in '95, rather than Manhattan, precisely because of Chic's cheap costs/taxes, new apt towers and undgd garages at home/office and valet pkg at restaurants, allowing even a mere IB analyst to drive around town everywhere in some new, leased C300, impervious to Chic's ugly weather (no worse than NYC if in a climate-controlled Mercedes commuting from garage to garage)....this walking, mass transit, cab nonsense is best left to ThirdWorld towns like Manhattan or London where allegedly high-income folks live in a primitive cesspool w/o cars, garages or modern HVAC
Ironically, all of those young IBers from mid-'90s fled Chic after a year to do tech M&A...and then tech hedge funds...in MenloPk and SF, where performance car culture and nr-ideal weather/topography prevail...thankfully, in more recent yrs, kids don't need to "serve" for a few yrs in cold/slushy and/or hot/humid places like NYC or Chic and can move to CA M&A, HF or PE straight from college
BTW, would prioritize garages at home/office over any "views" at home; any office has great views of Lake/skyline; just sleep at home anyway....views get old after first few days...and will spend most of one's time staring at various computer screens to figure out how to make enough money to flee to more hedonic places in next yr or so...