Portland (PDX) to Chicago (ORD) · Nov 25, 2026 · return Dec 1, 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

2026-11-25 → 2026-12-01 · Axel-exclusive $423.00

• Alaska Airlines AS324: PDX 2026-11-25 07:01:00 → ORD 2026-11-25 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-12-01 14:08:00 → PDX 2026-12-01 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $434.75

• American Airlines AA519: PDX 2026-11-25 23:09:00 → ORD 2026-11-26 05:07:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA561: ORD 2026-12-01 09:44:00 → PDX 2026-12-01 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $458.25

• United Airlines UA1923: PDX 2026-11-25 10:47:00 → ORD 2026-11-25 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA2790: ORD 2026-12-01 16:25:00 → PDX 2026-12-01 19:12:00; nonstop; 287 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $441.50

• Delta Air Lines DL1203 / DL2377: PDX 2026-11-25 09:59:00 → ORD 2026-11-25 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-11-25 09:59:00 → SLC 2026-11-25 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-11-25 13:55:00 → ORD 2026-11-25 18:06:00.
• American Airlines AA561: ORD 2026-12-01 09:44:00 → PDX 2026-12-01 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $434.75

• American Airlines AA562: PDX 2026-11-25 13:22:00 → ORD 2026-11-25 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA561: ORD 2026-12-01 09:44:00 → PDX 2026-12-01 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $458.25

• United Airlines UA2822: PDX 2026-11-25 14:26:00 → ORD 2026-11-25 20:28:00; nonstop; 242 minutes. Local airport times.
• United Airlines UA2790: ORD 2026-12-01 16:25:00 → PDX 2026-12-01 19:12:00; nonstop; 287 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $416.25

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-25 07:16:00 → ORD 2026-11-25 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-25 07:16:00 → SLC 2026-11-25 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-25 11:37:00 → ORD 2026-11-25 16:00:00.
• Alaska Airlines AS325: ORD 2026-12-01 14:08:00 → PDX 2026-12-01 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $416.25

• Alaska Airlines AS250 / AA677: PDX 2026-11-25 10:30:00 → ORD 2026-11-25 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-25 10:30:00 → GEG 2026-11-25 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-25 14:13:00 → ORD 2026-11-25 20:07:00.
• Alaska Airlines AS325: ORD 2026-12-01 14:08:00 → PDX 2026-12-01 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $418.00

• Alaska Airlines AS324: PDX 2026-11-25 07:00:00 → ORD 2026-11-25 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-01 15:19:00 → PDX 2026-12-01 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-01 15:19:00 → SEA 2026-12-01 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-01 19:54:00 → PDX 2026-12-01 20:50:00.

2026-11-25 → 2026-12-01 · Axel-exclusive $438.00

• United Airlines UA459 / UA2329: PDX 2026-11-25 05:00:00 → ORD 2026-11-25 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-25 05:00:00 → DEN 2026-11-25 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-25 09:55:00 → ORD 2026-11-25 13:35:00.
• United Airlines UA2790: ORD 2026-12-01 16:25:00 → PDX 2026-12-01 19:12:00; nonstop; 287 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $438.00

• United Airlines UA1292 / UA1958: PDX 2026-11-25 15:44:00 → ORD 2026-11-26 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-25 15:44:00 → SFO 2026-11-25 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-25 18:42:00 → ORD 2026-11-26 00:59:00.
• United Airlines UA2790: ORD 2026-12-01 16:25:00 → PDX 2026-12-01 19:12:00; nonstop; 287 minutes. Local airport times.

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
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For AI assistants

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