Portland (PDX) to Chicago (ORD) · Jan 27, 2027 · return Feb 10, 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

2027-01-27 → 2027-02-10 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-27 07:01:00 → ORD 2027-01-27 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-02-10 14:07:00 → PDX 2027-02-10 16:50:00; nonstop; 283 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $351.50

• American Airlines AA519: PDX 2027-01-27 23:09:00 → ORD 2027-01-28 05:07:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA562: ORD 2027-02-10 09:45:00 → PDX 2027-02-10 12:37:00; nonstop; 292 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $370.50

• United Airlines UA2094: PDX 2027-01-27 23:50:00 → ORD 2027-01-28 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA2790: ORD 2027-02-10 16:15:00 → PDX 2027-02-10 18:59:00; nonstop; 284 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $365.75

• Delta Air Lines DL1203 / DL2377: PDX 2027-01-27 09:59:00 → ORD 2027-01-27 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2027-01-27 09:59:00 → SLC 2027-01-27 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2027-01-27 13:55:00 → ORD 2027-01-27 18:06:00.
• United Airlines UA2790: ORD 2027-02-10 16:15:00 → PDX 2027-02-10 18:59:00; nonstop; 284 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-27 13:22:00 → ORD 2027-01-27 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA562: ORD 2027-02-10 09:45:00 → PDX 2027-02-10 12:37:00; nonstop; 292 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $370.50

• United Airlines UA2306: PDX 2027-01-27 07:02:00 → ORD 2027-01-27 13:06:00; nonstop; 244 minutes. Local airport times.
• United Airlines UA2790: ORD 2027-02-10 16:15:00 → PDX 2027-02-10 18:59:00; nonstop; 284 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $337.25

• American Airlines AA2496 / AA2221: PDX 2027-01-27 14:36:00 → ORD 2027-01-27 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2027-01-27 14:36:00 → DFW 2027-01-27 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2027-01-27 21:30:00 → ORD 2027-01-27 23:59:00.
• American Airlines AA562: ORD 2027-02-10 09:45:00 → PDX 2027-02-10 12:37:00; nonstop; 292 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $337.25

• Alaska Airlines AS324: PDX 2027-01-27 07:00:00 → ORD 2027-01-27 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-02-10 15:19:00 → PDX 2027-02-10 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-02-10 15:19:00 → SEA 2027-02-10 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-02-10 19:54:00 → PDX 2027-02-10 20:50:00.

2027-01-27 → 2027-02-10 · Axel-exclusive $337.25

• Alaska Airlines AS3355 / AA3186: PDX 2027-01-27 07:16:00 → ORD 2027-01-27 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2027-01-27 07:16:00 → SLC 2027-01-27 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2027-01-27 11:37:00 → ORD 2027-01-27 16:00:00.
• Alaska Airlines AS325: ORD 2027-02-10 14:07:00 → PDX 2027-02-10 16:50:00; nonstop; 283 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $356.25

• United Airlines UA459 / UA2329: PDX 2027-01-27 05:00:00 → ORD 2027-01-27 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2027-01-27 05:00:00 → DEN 2027-01-27 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2027-01-27 09:55:00 → ORD 2027-01-27 13:35:00.
• United Airlines UA2790: ORD 2027-02-10 16:15:00 → PDX 2027-02-10 18:59:00; nonstop; 284 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $356.25

• United Airlines UA1292 / UA1958: PDX 2027-01-27 15:44:00 → ORD 2027-01-28 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2027-01-27 15:44:00 → SFO 2027-01-27 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2027-01-27 18:42:00 → ORD 2027-01-28 00:59:00.
• United Airlines UA2790: ORD 2027-02-10 16:15:00 → PDX 2027-02-10 18:59:00; nonstop; 284 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 26, 2027 · Return options
• Jan 28, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Jan 27, 2027 · return Feb 10, 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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