Portland (PDX) to Chicago (ORD) · Dec 29, 2026 · return Jan 12, 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

2026-12-29 → 2027-01-12 · Axel-exclusive $396.00

• Alaska Airlines AS324: PDX 2026-12-29 07:00:00 → ORD 2026-12-29 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-12 14:08:00 → PDX 2027-01-12 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $407.00

• American Airlines AA3329: PDX 2026-12-29 23:31:00 → ORD 2026-12-30 05:25:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA2878: ORD 2027-01-12 17:05:00 → PDX 2027-01-12 19:55:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $429.00

• United Airlines UA2094: PDX 2026-12-29 23:50:00 → ORD 2026-12-30 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-12 20:17:00 → PDX 2027-01-12 23:07:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $407.00

• American Airlines AA562: PDX 2026-12-29 13:30:00 → ORD 2026-12-29 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA2878: ORD 2027-01-12 17:05:00 → PDX 2027-01-12 19:55:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $429.00

• United Airlines UA2306: PDX 2026-12-29 07:00:00 → ORD 2026-12-29 13:07:00; nonstop; 247 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-12 20:17:00 → PDX 2027-01-12 23:07:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $388.25

• American Airlines AA2496 / AA2221: PDX 2026-12-29 14:36:00 → ORD 2026-12-29 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-12-29 14:36:00 → DFW 2026-12-29 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-12-29 21:30:00 → ORD 2026-12-29 23:59:00.
• American Airlines AA2878: ORD 2027-01-12 17:05:00 → PDX 2027-01-12 19:55:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $389.75

• Alaska Airlines AS3355 / AA3186: PDX 2026-12-29 07:16:00 → ORD 2026-12-29 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-12-29 07:16:00 → SLC 2026-12-29 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-12-29 11:37:00 → ORD 2026-12-29 16:00:00.
• Alaska Airlines AS325: ORD 2027-01-12 14:08:00 → PDX 2027-01-12 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $389.75

• Alaska Airlines AS250 / AA677: PDX 2026-12-29 10:30:00 → ORD 2026-12-29 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-12-29 10:30:00 → GEG 2026-12-29 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-12-29 14:13:00 → ORD 2026-12-29 20:07:00.
• Alaska Airlines AS325: ORD 2027-01-12 14:08:00 → PDX 2027-01-12 17:05:00; nonstop; 297 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $391.25

• Alaska Airlines AS324: PDX 2026-12-29 07:01:00 → ORD 2026-12-29 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-12 15:19:00 → PDX 2027-01-12 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-12 15:19:00 → SEA 2027-01-12 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-12 19:54:00 → PDX 2027-01-12 20:50:00.

2026-12-29 → 2027-01-12 · Axel-exclusive $410.25

• United Airlines UA1292 / UA1958: PDX 2026-12-29 15:44:00 → ORD 2026-12-30 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-12-29 15:44:00 → SFO 2026-12-29 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-12-29 18:42:00 → ORD 2026-12-30 00:59:00.
• United Airlines UA2243: ORD 2027-01-12 20:17:00 → PDX 2027-01-12 23:07:00; nonstop; 290 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $410.25

• United Airlines UA459 / UA2329: PDX 2026-12-29 05:00:00 → ORD 2026-12-29 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-12-29 05:00:00 → DEN 2026-12-29 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-12-29 09:55:00 → ORD 2026-12-29 13:35:00.
• United Airlines UA2243: ORD 2027-01-12 20:17:00 → PDX 2027-01-12 23:07:00; nonstop; 290 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Dec 29, 2026 · return Jan 12, 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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