Chicago vs New York for Business Travel
Which is the easier business trip — Chicago or New York? 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 | New York |
|---|---|
| O’Hare (ORD) and Midway (MDW) airport rail available · 32 HQ guides | JFK, LaGuardia (LGA), and Newark (EWR) airport rail available · 51 HQ guides · NRF |
Which is easier to get around?
Chicago. One ride, one fare, no transfer. The O’Hare fare is $5, deducted on entry at O’Hare only against $2.50 everywhere else on the system, which is the city quietly charging an airport premium and still undercutting everyone. One caution for right now: the Blue Line O’Hare branch is on a modified construction schedule from 10 August to 9 October 2026. And rideshare moved upstairs: pickup is on the upper level at Terminals 2 and 3.
New York. Two steps, always. JFK is the $8.75 AirTrain plus a train: LIRR at about 30 minutes for $14.00 to $16.00, or the subway at roughly 50 minutes for $11.75 all-in. A cab is a $70 flat fare to Manhattan before surcharges.
So which is the better business trip?
Chicago, decisively, for the airport run. A 24-hour train from inside the terminal on one fare is the best airport access in the country, and the fact that it costs five dollars rather than nineteen is the whole argument.
New York wins everything after you arrive. Once you are in Manhattan you will not touch a car again, and no amount of Blue Line convenience compensates for Chicago meetings scattered up the North Shore. Judge the trip by where the meeting is, not by the airport: Chicago gets you downtown better, New York keeps you moving better once you are there.
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