Portland (PDX) to Chicago (MDW) · Jan 19, 2027 · return Jan 23, 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 (MDW) flight deals

2027-01-19 → 2027-01-23 · Axel-exclusive $350.00

• Southwest Airlines WN696: PDX 2027-01-19 11:20:00 → MDW 2027-01-19 17:05:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $400.00

• Delta Air Lines DL411 / DL4684: PDX 2027-01-19 23:20:00 → MDW 2027-01-20 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
  • DL411: PDX 2027-01-19 23:20:00 → DTW 2027-01-20 06:30:00; layover at DTW: 160 minutes.
  • DL4684: DTW 2027-01-20 09:10:00 → MDW 2027-01-20 09:46:00.
• Delta Air Lines DL4714 / DL2151: MDW 2027-01-23 17:29:00 → PDX 2027-01-23 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2027-01-23 17:29:00 → MSP 2027-01-23 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2027-01-23 21:59:00 → PDX 2027-01-23 23:46:00.

2027-01-19 → 2027-01-23 · Axel-exclusive $350.00

• Southwest Airlines WN3350: PDX 2027-01-19 23:30:00 → MDW 2027-01-20 05:15:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $340.00

• Southwest Airlines WN510 / WN576: PDX 2027-01-19 07:30:00 → MDW 2027-01-19 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
  • WN510: PDX 2027-01-19 07:30:00 → SJC 2027-01-19 09:20:00; layover at SJC: 110 minutes.
  • WN576: SJC 2027-01-19 11:10:00 → MDW 2027-01-19 17:15:00.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $340.00

• Southwest Airlines WN3348 / WN4990: PDX 2027-01-19 19:50:00 → MDW 2027-01-20 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
  • WN3348: PDX 2027-01-19 19:50:00 → LAS 2027-01-19 22:00:00; layover at LAS: 140 minutes.
  • WN4990: LAS 2027-01-20 00:20:00 → MDW 2027-01-20 05:40:00.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $340.00

• Southwest Airlines WN999 / WN1699: PDX 2027-01-19 09:45:00 → MDW 2027-01-19 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN999: PDX 2027-01-19 09:45:00 → DEN 2027-01-19 13:05:00; layover at DEN: 95 minutes.
  • WN1699: DEN 2027-01-19 14:40:00 → MDW 2027-01-19 17:55:00.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $340.00

• Southwest Airlines WN3040 / WN4963: PDX 2027-01-19 20:05:00 → MDW 2027-01-20 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
  • WN3040: PDX 2027-01-19 20:05:00 → PHX 2027-01-19 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2027-01-20 01:35:00 → MDW 2027-01-20 05:45:00.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; nonstop; 280 minutes. Local airport times.

2027-01-19 → 2027-01-23 · Axel-exclusive $340.00

• Southwest Airlines WN3361 / WN3573: PDX 2027-01-19 06:40:00 → MDW 2027-01-19 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
  • WN3361: PDX 2027-01-19 06:40:00 → SMF 2027-01-19 08:05:00; layover at SMF: 180 minutes.
  • WN3573: SMF 2027-01-19 11:05:00 → MDW 2027-01-19 17:05:00.
• Southwest Airlines WN2578: MDW 2027-01-23 22:00:00 → PDX 2027-01-24 00:40:00; 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.

Explore this route

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For AI assistants

• This page: Portland (PDX) to Chicago (MDW) · Jan 19, 2027 · return Jan 23, 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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