Portland (PDX) to Chicago (ORD) · Dec 26, 2026 · return Jan 1, 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

2026-12-26 → 2027-01-01 · Axel-exclusive $455.40

• Alaska Airlines AS324: PDX 2026-12-26 07:00:00 → ORD 2026-12-26 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-01 14:08:00 → PDX 2027-01-01 16:58:00; nonstop; 290 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $468.05

• American Airlines AA563: PDX 2026-12-26 13:46:00 → ORD 2026-12-26 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-01 10:05:00 → PDX 2027-01-01 13:01:00; nonstop; 296 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $493.35

• United Airlines UA2094: PDX 2026-12-26 23:50:00 → ORD 2026-12-27 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA1786: ORD 2027-01-01 19:45:00 → PDX 2027-01-01 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $486.60

• Delta Air Lines DL1203 / DL2377: PDX 2026-12-26 09:59:00 → ORD 2026-12-26 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-12-26 09:59:00 → SLC 2026-12-26 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-12-26 13:55:00 → ORD 2026-12-26 18:06:00.
• United Airlines UA1786: ORD 2027-01-01 19:45:00 → PDX 2027-01-01 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $468.05

• American Airlines AA3329: PDX 2026-12-26 23:11:00 → ORD 2026-12-27 05:15:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-01 10:05:00 → PDX 2027-01-01 13:01:00; nonstop; 296 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $493.35

• United Airlines UA2306: PDX 2026-12-26 07:02:00 → ORD 2026-12-26 13:06:00; nonstop; 244 minutes. Local airport times.
• United Airlines UA1786: ORD 2027-01-01 19:45:00 → PDX 2027-01-01 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $442.75

• Alaska Airlines AS3355 / AA3186: PDX 2026-12-26 07:16:00 → ORD 2026-12-26 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-12-26 07:16:00 → SLC 2026-12-26 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-12-26 11:37:00 → ORD 2026-12-26 16:00:00.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-01 15:19:00 → PDX 2027-01-01 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-01 15:19:00 → SEA 2027-01-01 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-01 19:54:00 → PDX 2027-01-01 20:50:00.

2026-12-26 → 2027-01-01 · Axel-exclusive $447.80

• American Airlines AA2496 / AA2221: PDX 2026-12-26 14:36:00 → ORD 2026-12-26 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-12-26 14:36:00 → DFW 2026-12-26 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-12-26 21:30:00 → ORD 2026-12-26 23:59:00.
• American Airlines AA563: ORD 2027-01-01 10:05:00 → PDX 2027-01-01 13:01:00; nonstop; 296 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $449.50

• Alaska Airlines AS324: PDX 2026-12-26 07:00:00 → ORD 2026-12-26 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-01 15:19:00 → PDX 2027-01-01 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-01 15:19:00 → SEA 2027-01-01 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-01 19:54:00 → PDX 2027-01-01 20:50:00.

2026-12-26 → 2027-01-01 · Axel-exclusive $473.10

• United Airlines UA459 / UA2329: PDX 2026-12-26 05:00:00 → ORD 2026-12-26 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-12-26 05:00:00 → DEN 2026-12-26 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-12-26 09:55:00 → ORD 2026-12-26 13:35:00.
• United Airlines UA1786: ORD 2027-01-01 19:45:00 → PDX 2027-01-01 22:27:00; nonstop; 282 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $475.65

• United Airlines UA2306: PDX 2026-12-26 07:00:00 → ORD 2026-12-26 13:07:00; nonstop; 247 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2027-01-01 08:58:00 → PDX 2027-01-01 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2027-01-01 08:58:00 → YVR 2027-01-01 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2027-01-01 14:25:00 → PDX 2027-01-01 14:41:00.

Explore this route

• All dates for this route
• Dec 25, 2026 · Return options
• Dec 27, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Dec 26, 2026 · return Jan 1, 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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