Chicago vs the Bay Area for Business Travel
Which is the easier business trip — Chicago or the Bay Area? Airports, getting around, and what’s actually there, compared.
Two very different business-travel cities. Here is the honest side-by-side — the airports, whether you can skip the rental, and how much is actually headquartered there.
| Chicago | the Bay Area |
|---|---|
| O’Hare (ORD) and Midway (MDW) airport rail available · 21 HQ guides | SFO, Oakland (OAK), and San Jose (SJC) airport rail available · 36 HQ guides · Dreamforce, SaaStr, RSA |
Which is easier to get around?
Chicago: Both Chicago airports are on the L (Blue from O’Hare, Orange from Midway) — train for downtown, Metra or car for the suburbs. the Bay Area: The Bay Area is two trips: BART from SFO/Oakland for the city, but Silicon Valley is a rental-car region off the rail lines.
So which is the better business trip?
Neither is dramatically easier to move around — both have airport rail into the core. The real difference is where your client sits and how spread out the metro is; check the company’s guide.
For the specifics, see business travel to Chicago and business travel to the Bay Area.
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