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Chicago vs Seattle for Business Travel

By Rachel Julian, Editor-in-Chief · · 3 min read

Which is the easier business trip — Chicago or Seattle? Airports, getting around, and what’s actually there, compared.

Direct answer: Chicago’s train runs all night; Seattle’s runs every 8 to 10 minutes when the line runs normally, though Sound Transit’s alerts page is worth a look first, because single-tracking south of Stadium stretches the airport segment well past that on a flat $3.00. Frequency against hours, and which you need depends on your flight.

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.

ChicagoSeattle
O’Hare (ORD) and Midway (MDW)
airport rail available · 32 HQ guides		Seattle-Tacoma (SEA)
airport rail available · 16 HQ guides

Which is easier to get around?

Chicago. 24 hours a day, seven days a week, 40 to 45 minutes to downtown, $5 from O’Hare against $2.50 elsewhere on the system. Currently on a modified schedule to 9 October 2026.

Seattle. 38 minutes, flat $3.00 with under-18s free, and now the 2 Line across the lake to Redmond Technology Station for the Eastside. Two frictions: a 7-to-9-minute walk from baggage claim and rideshare on the 3rd floor while the train is on the 4th.

So which is the better business trip?

Seattle, for a normal working day. Cheaper, more frequent, and the 2 Line now reaches the Eastside employers that used to force a rental.

Chicago, for the day that goes wrong. Overnight service is worth more than eight-minute headways the first time you land at 1 a.m., and O’Hare’s nonstop network gives you options Seattle cannot. Seattle is the better ordinary trip; Chicago is the better contingency.

On the road for work a lot?

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Sources: every transit figure is the operating agency’s or airport authority’s own page, linked beside the claim, all read 2026-08-08. Where two official sources disagree the page names which one it follows and why. Fares and service patterns change; check the link before you travel. The comparison is this desk’s judgement, grounded in those published figures. Not paid placements. Airport drive times shown in the fact block above are approximate and are this desk’s own estimate, not a figure any airport or transit agency publishes; confirm before booking.

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