Portland (PDX) to Chicago (ORD) · Jan 2, 2027 · return Jan 5, 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

2027-01-02 → 2027-01-05 · Axel-exclusive $383.40

• Alaska Airlines AS324: PDX 2027-01-02 07:00:00 → ORD 2027-01-02 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-05 14:08:00 → PDX 2027-01-05 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $394.05

• American Airlines AA3329: PDX 2027-01-02 23:11:00 → ORD 2027-01-03 05:15:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA2878: ORD 2027-01-05 17:05:00 → PDX 2027-01-05 19:55:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $415.35

• United Airlines UA2094: PDX 2027-01-02 23:50:00 → ORD 2027-01-03 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-05 20:17:00 → PDX 2027-01-05 23:07:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $409.45

• Delta Air Lines DL1203 / DL2377: PDX 2027-01-02 09:59:00 → ORD 2027-01-02 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2027-01-02 09:59:00 → SLC 2027-01-02 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2027-01-02 13:55:00 → ORD 2027-01-02 18:06:00.
• United Airlines UA2243: ORD 2027-01-05 20:17:00 → PDX 2027-01-05 23:07:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $394.05

• American Airlines AA563: PDX 2027-01-02 13:46:00 → ORD 2027-01-02 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA2878: ORD 2027-01-05 17:05:00 → PDX 2027-01-05 19:55:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $415.35

• United Airlines UA2306: PDX 2027-01-02 07:02:00 → ORD 2027-01-02 13:06:00; nonstop; 244 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-05 20:17:00 → PDX 2027-01-05 23:07:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $376.35

• American Airlines AA2496 / AA2221: PDX 2027-01-02 14:36:00 → ORD 2027-01-02 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2027-01-02 14:36:00 → DFW 2027-01-02 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2027-01-02 21:30:00 → ORD 2027-01-02 23:59:00.
• American Airlines AA2878: ORD 2027-01-05 17:05:00 → PDX 2027-01-05 19:55:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $377.50

• Alaska Airlines AS3355 / AA3186: PDX 2027-01-02 07:16:00 → ORD 2027-01-02 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2027-01-02 07:16:00 → SLC 2027-01-02 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2027-01-02 11:37:00 → ORD 2027-01-02 16:00:00.
• Alaska Airlines AS325: ORD 2027-01-05 14:08:00 → PDX 2027-01-05 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $378.65

• Alaska Airlines AS324: PDX 2027-01-02 07:00:00 → ORD 2027-01-02 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-05 15:19:00 → PDX 2027-01-05 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-05 15:19:00 → SEA 2027-01-05 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-05 19:54:00 → PDX 2027-01-05 20:50:00.

2027-01-02 → 2027-01-05 · Axel-exclusive $397.65

• United Airlines UA1292 / UA1958: PDX 2027-01-02 15:44:00 → ORD 2027-01-03 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2027-01-02 15:44:00 → SFO 2027-01-02 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2027-01-02 18:42:00 → ORD 2027-01-03 00:59:00.
• United Airlines UA2243: ORD 2027-01-05 20:17:00 → PDX 2027-01-05 23:07:00; nonstop; 290 minutes. Local airport times.

2027-01-02 → 2027-01-05 · Axel-exclusive $397.65

• United Airlines UA459 / UA2329: PDX 2027-01-02 05:00:00 → ORD 2027-01-02 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2027-01-02 05:00:00 → DEN 2027-01-02 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2027-01-02 09:55:00 → ORD 2027-01-02 13:35:00.
• United Airlines UA2243: ORD 2027-01-05 20:17:00 → PDX 2027-01-05 23:07:00; nonstop; 290 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 1, 2027 · Return options
• Jan 3, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Jan 2, 2027 · return Jan 5, 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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