Best & latest deal
$197 RT
Gone
Portland to Chicago, without the $315+ fare.
This route normally runs $315+ round trip. PDXplore subscribers have flown it for $197. Here's the route, the receipts, and how to catch the next one.
$315+
typical round trip
$197
our best fare ever
2
deals sent since Nov 2025
The fares that matter
Two sends to Chicago since Nov 2025. The next one lands with subscribers first.
Route sheet
- Route
- PDX → Chicago (ORD / MDW)
- Airlines we've sent
- Southwest Airlines
- When fares dip
- Jan to May departures
- Deal alert speed
- Mistake fares: instant · Everything else: Thursday (Premium), Friday (free)
We have sent two Chicago deals since Nov 2025. Economy has reached $197 against a normal $315+, with departures across Jan to May. We keep the route on our board for the next one.
Premium members get Chicago mistake-fare alerts the minute we catch them. The free list hears Friday.
See PremiumThe next Chicago deal is already boarding.
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