Alaska Airlines Flights from Portland to Chicago
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1 Passenger
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Lowest fares from Portland to Chicago
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One-way low-fare flights Portland to Chicago.*
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From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: May 12, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Apr 25, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Mar 31, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Feb 18, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Mar 17, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: May 9, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Feb 3, 2026 | From $99 Seen: 13 hours ago | |
| Portland (PDX) | Chicago (ORD) | One-way | Saver | Depart: Apr 14, 2026 | From $99 Seen: 13 hours ago |
*Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.