Portland (PDX) to Chicago (ORD) · Dec 24, 2026 · return Jan 7, 2027

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

2026-12-24 → 2027-01-07 · Axel-exclusive $414.00

• Alaska Airlines AS324: PDX 2026-12-24 07:00:00 → ORD 2026-12-24 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-07 14:08:00 → PDX 2027-01-07 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $425.50

• American Airlines AA562: PDX 2026-12-24 13:22:00 → ORD 2026-12-24 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-07 10:00:00 → PDX 2027-01-07 12:56:00; nonstop; 296 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $448.50

• United Airlines UA2822: PDX 2026-12-24 14:26:00 → ORD 2026-12-24 20:28:00; nonstop; 242 minutes. Local airport times.
• United Airlines UA1786: ORD 2027-01-07 19:45:00 → PDX 2027-01-07 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $448.50

• United Airlines UA1923: PDX 2026-12-24 10:43:00 → ORD 2026-12-24 16:49:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2027-01-07 19:45:00 → PDX 2027-01-07 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $391.00

• American Airlines AA2496 / AA2221: PDX 2026-12-24 14:36:00 → ORD 2026-12-24 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-12-24 14:36:00 → DFW 2026-12-24 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-12-24 21:30:00 → ORD 2026-12-24 23:59:00.
• American Airlines AA3186 / AS3430: ORD 2027-01-07 08:10:00 → PDX 2027-01-07 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2027-01-07 08:10:00 → SLC 2027-01-07 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2027-01-07 12:32:00 → PDX 2027-01-07 13:48:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $409.25

• Alaska Airlines AS324: PDX 2026-12-24 07:00:00 → ORD 2026-12-24 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-07 15:19:00 → PDX 2027-01-07 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-07 15:19:00 → SEA 2027-01-07 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-07 19:54:00 → PDX 2027-01-07 20:50:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $411.25

• American Airlines AA562: PDX 2026-12-24 13:30:00 → ORD 2026-12-24 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA3186 / AS3430: ORD 2027-01-07 08:10:00 → PDX 2027-01-07 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2027-01-07 08:10:00 → SLC 2027-01-07 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2027-01-07 12:32:00 → PDX 2027-01-07 13:48:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $428.25

• United Airlines UA1292 / UA1958: PDX 2026-12-24 15:44:00 → ORD 2026-12-25 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-12-24 15:44:00 → SFO 2026-12-24 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-12-24 18:42:00 → ORD 2026-12-25 00:59:00.
• United Airlines UA1786: ORD 2027-01-07 19:45:00 → PDX 2027-01-07 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $428.25

• United Airlines UA459 / UA2329: PDX 2026-12-24 05:00:00 → ORD 2026-12-24 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-12-24 05:00:00 → DEN 2026-12-24 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-12-24 09:55:00 → ORD 2026-12-24 13:35:00.
• United Airlines UA1786: ORD 2027-01-07 19:45:00 → PDX 2027-01-07 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $434.25

• United Airlines UA1923: PDX 2026-12-24 10:45:00 → ORD 2026-12-24 16:51:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2027-01-07 08:58:00 → PDX 2027-01-07 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2027-01-07 08:58:00 → YVR 2027-01-07 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2027-01-07 14:25:00 → PDX 2027-01-07 14:41:00.

Explore this route

• All dates for this route
• Dec 23, 2026 · Return options
• Dec 25, 2026 · Return options
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For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Dec 24, 2026 · return Jan 7, 2027: 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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