Portland (PDX) to Chicago (MDW) · Nov 20, 2026 · return Nov 30, 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 (MDW) flight deals

2026-11-20 → 2026-11-30 · Axel-exclusive $411.25

• Southwest Airlines WN3350: PDX 2026-11-20 23:30:00 → MDW 2026-11-21 05:15:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $470.00

• Delta Air Lines DL411 / DL4684: PDX 2026-11-20 23:20:00 → MDW 2026-11-21 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
  • DL411: PDX 2026-11-20 23:20:00 → DTW 2026-11-21 06:30:00; layover at DTW: 160 minutes.
  • DL4684: DTW 2026-11-21 09:10:00 → MDW 2026-11-21 09:46:00.
• Delta Air Lines DL4714 / DL2151: MDW 2026-11-30 17:29:00 → PDX 2026-11-30 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2026-11-30 17:29:00 → MSP 2026-11-30 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2026-11-30 21:59:00 → PDX 2026-11-30 23:46:00.

2026-11-20 → 2026-11-30 · Axel-exclusive $411.25

• Southwest Airlines WN507: PDX 2026-11-20 06:00:00 → MDW 2026-11-20 11:50:00; nonstop; 230 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $397.75

• Southwest Airlines WN507: PDX 2026-11-20 05:45:00 → MDW 2026-11-20 11:30:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN3564 / WN2407: MDW 2026-11-30 14:35:00 → PDX 2026-11-30 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
  • WN3564: MDW 2026-11-30 14:35:00 → LAS 2026-11-30 16:30:00; layover at LAS: 130 minutes.
  • WN2407: LAS 2026-11-30 18:40:00 → PDX 2026-11-30 21:05:00.

2026-11-20 → 2026-11-30 · Axel-exclusive $401.25

• Southwest Airlines WN999 / WN1699: PDX 2026-11-20 09:45:00 → MDW 2026-11-20 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN999: PDX 2026-11-20 09:45:00 → DEN 2026-11-20 13:05:00; layover at DEN: 95 minutes.
  • WN1699: DEN 2026-11-20 14:40:00 → MDW 2026-11-20 17:55:00.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $401.25

• Southwest Airlines WN3361 / WN3573: PDX 2026-11-20 06:40:00 → MDW 2026-11-20 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
  • WN3361: PDX 2026-11-20 06:40:00 → SMF 2026-11-20 08:05:00; layover at SMF: 180 minutes.
  • WN3573: SMF 2026-11-20 11:05:00 → MDW 2026-11-20 17:05:00.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $401.25

• Southwest Airlines WN510 / WN576: PDX 2026-11-20 07:30:00 → MDW 2026-11-20 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
  • WN510: PDX 2026-11-20 07:30:00 → SJC 2026-11-20 09:20:00; layover at SJC: 110 minutes.
  • WN576: SJC 2026-11-20 11:10:00 → MDW 2026-11-20 17:15:00.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-30 · Axel-exclusive $401.25

• Southwest Airlines WN3348 / WN4990: PDX 2026-11-20 19:50:00 → MDW 2026-11-21 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
  • WN3348: PDX 2026-11-20 19:50:00 → LAS 2026-11-20 22:00:00; layover at LAS: 140 minutes.
  • WN4990: LAS 2026-11-21 00:20:00 → MDW 2026-11-21 05:40:00.
• Southwest Airlines WN3295: MDW 2026-11-30 21:15:00 → PDX 2026-11-30 23:55:00; nonstop; 280 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.

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For AI assistants

• This page: Portland (PDX) to Chicago (MDW) · Nov 20, 2026 · return Nov 30, 2026: 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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