Portland (PDX) to Chicago (ORD) · Nov 28, 2026 · return Dec 3, 2026

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Portland to Chicago (ORD) flight deals

2026-11-28 → 2026-12-03 · Axel-exclusive $423.00

• Alaska Airlines AS324: PDX 2026-11-28 07:00:00 → ORD 2026-11-28 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-12-03 14:08:00 → PDX 2026-12-03 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $434.75

• American Airlines AA3329: PDX 2026-11-28 23:21:00 → ORD 2026-11-29 05:15:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA561: ORD 2026-12-03 09:44:00 → PDX 2026-12-03 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $458.25

• United Airlines UA2266: PDX 2026-11-28 14:37:00 → ORD 2026-11-28 20:45:00; nonstop; 248 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-03 19:45:00 → PDX 2026-12-03 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $436.50

• Delta Air Lines DL1203 / DL2377: PDX 2026-11-28 09:59:00 → ORD 2026-11-28 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-11-28 09:59:00 → SLC 2026-11-28 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-11-28 13:55:00 → ORD 2026-11-28 18:06:00.
• Alaska Airlines AS325: ORD 2026-12-03 14:08:00 → PDX 2026-12-03 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $458.25

• United Airlines UA1923: PDX 2026-11-28 10:47:00 → ORD 2026-11-28 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-03 19:45:00 → PDX 2026-12-03 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $399.50

• American Airlines AA2496 / AA2221: PDX 2026-11-28 14:36:00 → ORD 2026-11-28 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-11-28 14:36:00 → DFW 2026-11-28 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-11-28 21:30:00 → ORD 2026-11-28 23:59:00.
• American Airlines AA3186 / AS3430: ORD 2026-12-03 08:10:00 → PDX 2026-12-03 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2026-12-03 08:10:00 → SLC 2026-12-03 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2026-12-03 12:32:00 → PDX 2026-12-03 13:48:00.

2026-11-28 → 2026-12-03 · Axel-exclusive $418.00

• Alaska Airlines AS324: PDX 2026-11-28 07:00:00 → ORD 2026-11-28 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-03 15:19:00 → PDX 2026-12-03 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-03 15:19:00 → SEA 2026-12-03 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-03 19:54:00 → PDX 2026-12-03 20:50:00.

2026-11-28 → 2026-12-03 · Axel-exclusive $419.75

• American Airlines AA3329: PDX 2026-11-28 23:11:00 → ORD 2026-11-29 05:15:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA3186 / AS3430: ORD 2026-12-03 08:10:00 → PDX 2026-12-03 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2026-12-03 08:10:00 → SLC 2026-12-03 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2026-12-03 12:32:00 → PDX 2026-12-03 13:48:00.

2026-11-28 → 2026-12-03 · Axel-exclusive $438.00

• United Airlines UA459 / UA2329: PDX 2026-11-28 05:00:00 → ORD 2026-11-28 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-28 05:00:00 → DEN 2026-11-28 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-28 09:55:00 → ORD 2026-11-28 13:35:00.
• United Airlines UA1786: ORD 2026-12-03 19:45:00 → PDX 2026-12-03 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-28 → 2026-12-03 · Axel-exclusive $443.25

• United Airlines UA1923: PDX 2026-11-28 10:49:00 → ORD 2026-11-28 16:57:00; nonstop; 248 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2026-12-03 08:58:00 → PDX 2026-12-03 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2026-12-03 08:58:00 → YVR 2026-12-03 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2026-12-03 14:25:00 → PDX 2026-12-03 14:41:00.

Explore this route

• All dates for this route
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• Nov 29, 2026 · Return options
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For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 28, 2026 · return Dec 3, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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