Chicago (MDW) to Portland (PDX) · Jan 17, 2027 · return Jan 21, 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: Chicago to Portland (PDX) flight deals

2027-01-17 → 2027-01-21 · Axel-exclusive $342.00

• Southwest Airlines WN3295: MDW 2027-01-17 21:30:00 → PDX 2027-01-18 00:15:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $370.50

• Delta Air Lines DL4714 / DL2151: MDW 2027-01-17 17:29:00 → PDX 2027-01-17 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2027-01-17 17:29:00 → MSP 2027-01-17 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2027-01-17 21:59:00 → PDX 2027-01-17 23:46:00.
• Delta Air Lines DL411 / DL4684: PDX 2027-01-21 23:20:00 → MDW 2027-01-22 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
  • DL411: PDX 2027-01-21 23:20:00 → DTW 2027-01-22 06:30:00; layover at DTW: 160 minutes.
  • DL4684: DTW 2027-01-22 09:10:00 → MDW 2027-01-22 09:46:00.

2027-01-17 → 2027-01-21 · Axel-exclusive $342.00

• Southwest Airlines WN2087: MDW 2027-01-17 10:10:00 → PDX 2027-01-17 12:45:00; nonstop; 275 minutes. Local airport times.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $327.75

• Southwest Airlines WN3035 / WN314: MDW 2027-01-17 10:15:00 → PDX 2027-01-17 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
  • WN3035: MDW 2027-01-17 10:15:00 → SJC 2027-01-17 13:00:00; layover at SJC: 60 minutes.
  • WN314: SJC 2027-01-17 14:00:00 → PDX 2027-01-17 15:50:00.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $327.75

• Southwest Airlines WN2995 / WN969: MDW 2027-01-17 05:05:00 → PDX 2027-01-17 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2027-01-17 05:05:00 → PHX 2027-01-17 07:55:00; layover at PHX: 65 minutes.
  • WN969: PHX 2027-01-17 09:00:00 → PDX 2027-01-17 10:50:00.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $327.75

• Southwest Airlines WN3564 / WN2407: MDW 2027-01-17 14:35:00 → PDX 2027-01-17 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
  • WN3564: MDW 2027-01-17 14:35:00 → LAS 2027-01-17 16:30:00; layover at LAS: 130 minutes.
  • WN2407: LAS 2027-01-17 18:40:00 → PDX 2027-01-17 21:05:00.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $327.75

• Southwest Airlines WN4606 / WN1196: MDW 2027-01-17 14:35:00 → PDX 2027-01-17 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
  • WN4606: MDW 2027-01-17 14:35:00 → DEN 2027-01-17 16:15:00; layover at DEN: 130 minutes.
  • WN1196: DEN 2027-01-17 18:25:00 → PDX 2027-01-17 20:15:00.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-17 → 2027-01-21 · Axel-exclusive $327.75

• Southwest Airlines WN3174 / WN2916: MDW 2027-01-17 10:00:00 → PDX 2027-01-17 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
  • WN3174: MDW 2027-01-17 10:00:00 → OAK 2027-01-17 12:40:00; layover at OAK: 75 minutes.
  • WN2916: OAK 2027-01-17 13:55:00 → PDX 2027-01-17 15:35:00.
• Southwest Airlines WN3350: PDX 2027-01-21 23:30:00 → MDW 2027-01-22 05:15:00; nonstop; 225 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

• All dates for this route
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For AI assistants

• This page: Chicago (MDW) to Portland (PDX) · Jan 17, 2027 · return Jan 21, 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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