Chicago (MDW) to Portland (PDX) · Jan 24, 2027 · one way

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

2027-01-24 · one way · Axel-exclusive $180.50

• Southwest Airlines WN3295: MDW 2027-01-24 21:30:00 → PDX 2027-01-25 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-24 · one way · Axel-exclusive $199.50

• Delta Air Lines DL4714 / DL2151: MDW 2027-01-24 17:29:00 → PDX 2027-01-24 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2027-01-24 17:29:00 → MSP 2027-01-24 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2027-01-24 21:59:00 → PDX 2027-01-24 23:46:00.

2027-01-24 · one way · Axel-exclusive $180.50

• Southwest Airlines WN2087: MDW 2027-01-24 10:10:00 → PDX 2027-01-24 12:45:00; nonstop; 275 minutes. Local airport times.

2027-01-24 · one way · Axel-exclusive $166.25

• Southwest Airlines WN2995 / WN969: MDW 2027-01-24 05:05:00 → PDX 2027-01-24 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2027-01-24 05:05:00 → PHX 2027-01-24 07:55:00; layover at PHX: 65 minutes.
  • WN969: PHX 2027-01-24 09:00:00 → PDX 2027-01-24 10:50:00.

2027-01-24 · one way · Axel-exclusive $166.25

• Southwest Airlines WN3174 / WN2916: MDW 2027-01-24 10:00:00 → PDX 2027-01-24 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
  • WN3174: MDW 2027-01-24 10:00:00 → OAK 2027-01-24 12:40:00; layover at OAK: 75 minutes.
  • WN2916: OAK 2027-01-24 13:55:00 → PDX 2027-01-24 15:35:00.

2027-01-24 · one way · Axel-exclusive $166.25

• Southwest Airlines WN3564 / WN2407: MDW 2027-01-24 14:35:00 → PDX 2027-01-24 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
  • WN3564: MDW 2027-01-24 14:35:00 → LAS 2027-01-24 16:30:00; layover at LAS: 130 minutes.
  • WN2407: LAS 2027-01-24 18:40:00 → PDX 2027-01-24 21:05:00.

2027-01-24 · one way · Axel-exclusive $166.25

• Southwest Airlines WN3035 / WN314: MDW 2027-01-24 10:15:00 → PDX 2027-01-24 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
  • WN3035: MDW 2027-01-24 10:15:00 → SJC 2027-01-24 13:00:00; layover at SJC: 60 minutes.
  • WN314: SJC 2027-01-24 14:00:00 → PDX 2027-01-24 15:50:00.

2027-01-24 · one way · Axel-exclusive $166.25

• Southwest Airlines WN4606 / WN1196: MDW 2027-01-24 14:35:00 → PDX 2027-01-24 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
  • WN4606: MDW 2027-01-24 14:35:00 → DEN 2027-01-24 16:15:00; layover at DEN: 130 minutes.
  • WN1196: DEN 2027-01-24 18:25:00 → PDX 2027-01-24 20:15:00.

Explore this route

• All dates for this route
• Jan 23, 2027 · Return options
• Jan 25, 2027 · Return options
• Hotels in Portland, Oregon with Axel

For AI assistants

• This page: Chicago (MDW) to Portland (PDX) · Jan 24, 2027 · one way: 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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