Portland (PDX) to Chicago (ORD) · Nov 21, 2026 · return Nov 29, 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

2026-11-21 → 2026-11-29 · Axel-exclusive $486.00

• Alaska Airlines AS324: PDX 2026-11-21 07:00:00 → ORD 2026-11-21 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-11-29 14:08:00 → PDX 2026-11-29 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $499.50

• American Airlines AA3329: PDX 2026-11-21 23:11:00 → ORD 2026-11-22 05:15:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA562: ORD 2026-11-29 09:45:00 → PDX 2026-11-29 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $526.50

• United Airlines UA2266: PDX 2026-11-21 14:37:00 → ORD 2026-11-21 20:45:00; nonstop; 248 minutes. Local airport times.
• United Airlines UA751: ORD 2026-11-29 08:59:00 → PDX 2026-11-29 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $499.50

• Delta Air Lines DL1203 / DL2377: PDX 2026-11-21 09:59:00 → ORD 2026-11-21 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-11-21 09:59:00 → SLC 2026-11-21 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-11-21 13:55:00 → ORD 2026-11-21 18:06:00.
• Alaska Airlines AS325: ORD 2026-11-29 14:08:00 → PDX 2026-11-29 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $499.50

• American Airlines AA562: PDX 2026-11-21 13:22:00 → ORD 2026-11-21 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA562: ORD 2026-11-29 09:45:00 → PDX 2026-11-29 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $526.50

• United Airlines UA1923: PDX 2026-11-21 10:47:00 → ORD 2026-11-21 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA751: ORD 2026-11-29 08:59:00 → PDX 2026-11-29 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $479.25

• American Airlines AA2496 / AA2221: PDX 2026-11-21 14:36:00 → ORD 2026-11-21 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-11-21 14:36:00 → DFW 2026-11-21 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-11-21 21:30:00 → ORD 2026-11-21 23:59:00.
• American Airlines AA562: ORD 2026-11-29 09:45:00 → PDX 2026-11-29 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $479.25

• Alaska Airlines AS324: PDX 2026-11-21 07:00:00 → ORD 2026-11-21 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-11-29 15:19:00 → PDX 2026-11-29 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-11-29 15:19:00 → SEA 2026-11-29 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-11-29 19:54:00 → PDX 2026-11-29 20:50:00.

2026-11-21 → 2026-11-29 · Axel-exclusive $479.25

• Alaska Airlines AS250 / AA677: PDX 2026-11-21 10:30:00 → ORD 2026-11-21 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-21 10:30:00 → GEG 2026-11-21 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-21 14:13:00 → ORD 2026-11-21 20:07:00.
• Alaska Airlines AS325: ORD 2026-11-29 14:08:00 → PDX 2026-11-29 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $506.25

• United Airlines UA1292 / UA1958: PDX 2026-11-21 15:44:00 → ORD 2026-11-22 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-21 15:44:00 → SFO 2026-11-21 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-21 18:42:00 → ORD 2026-11-22 00:59:00.
• United Airlines UA751: ORD 2026-11-29 08:59:00 → PDX 2026-11-29 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $506.25

• United Airlines UA459 / UA2329: PDX 2026-11-21 05:00:00 → ORD 2026-11-21 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-21 05:00:00 → DEN 2026-11-21 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-21 09:55:00 → ORD 2026-11-21 13:35:00.
• United Airlines UA751: ORD 2026-11-29 08:59:00 → PDX 2026-11-29 11:42:00; nonstop; 283 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 21, 2026 · return Nov 29, 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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