Portland (PDX) to Chicago (ORD) · Nov 20, 2026 · return Dec 4, 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

2026-11-20 → 2026-12-04 · Axel-exclusive $360.00

• Alaska Airlines AS324: PDX 2026-11-20 07:01:00 → ORD 2026-11-20 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-12-04 14:08:00 → PDX 2026-12-04 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $370.00

• American Airlines AA563: PDX 2026-11-20 13:46:00 → ORD 2026-11-20 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $390.00

• United Airlines UA2266: PDX 2026-11-20 14:34:00 → ORD 2026-11-20 20:40:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $370.00

• American Airlines AA3329: PDX 2026-11-20 23:13:00 → ORD 2026-11-21 05:07:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $390.00

• United Airlines UA1923: PDX 2026-11-20 10:43:00 → ORD 2026-11-20 16:49:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $350.00

• Alaska Airlines AS250 / AA677: PDX 2026-11-20 10:30:00 → ORD 2026-11-20 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-20 10:30:00 → GEG 2026-11-20 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-20 14:13:00 → ORD 2026-11-20 20:07:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-20 → 2026-12-04 · Axel-exclusive $350.00

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-20 07:16:00 → ORD 2026-11-20 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-20 07:16:00 → SLC 2026-11-20 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-20 11:37:00 → ORD 2026-11-20 16:00:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-20 → 2026-12-04 · Axel-exclusive $355.00

• Alaska Airlines AS324: PDX 2026-11-20 07:00:00 → ORD 2026-11-20 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-20 → 2026-12-04 · Axel-exclusive $355.00

• American Airlines AA2496 / AA2221: PDX 2026-11-20 14:36:00 → ORD 2026-11-20 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-11-20 14:36:00 → DFW 2026-11-20 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-11-20 21:30:00 → ORD 2026-11-20 23:59:00.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $375.00

• United Airlines UA1292 / UA1958: PDX 2026-11-20 15:44:00 → ORD 2026-11-21 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-20 15:44:00 → SFO 2026-11-20 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-20 18:42:00 → ORD 2026-11-21 00:59:00.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-12-04 · Axel-exclusive $375.00

• United Airlines UA1923: PDX 2026-11-20 10:47:00 → ORD 2026-11-20 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2026-12-04 08:58:00 → PDX 2026-12-04 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2026-12-04 08:58:00 → YVR 2026-12-04 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2026-12-04 14:25:00 → PDX 2026-12-04 14:41:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Nov 19, 2026 · Return options
• Nov 21, 2026 · Return options
• Hotels in Chicago with Axel

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