Portland (PDX) to Chicago (MDW) · Jan 1, 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 (MDW) flight deals

2027-01-01 → 2027-01-05 · Axel-exclusive $402.50

• Southwest Airlines WN507: PDX 2027-01-01 05:25:00 → MDW 2027-01-01 11:15:00; nonstop; 230 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $460.00

• Delta Air Lines DL411 / DL4684: PDX 2027-01-01 23:20:00 → MDW 2027-01-02 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
  • DL411: PDX 2027-01-01 23:20:00 → DTW 2027-01-02 06:30:00; layover at DTW: 160 minutes.
  • DL4684: DTW 2027-01-02 09:10:00 → MDW 2027-01-02 09:46:00.
• Delta Air Lines DL4714 / DL2151: MDW 2027-01-05 17:29:00 → PDX 2027-01-05 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2027-01-05 17:29:00 → MSP 2027-01-05 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2027-01-05 21:59:00 → PDX 2027-01-05 23:46:00.

2027-01-01 → 2027-01-05 · Axel-exclusive $402.50

• Southwest Airlines WN3350: PDX 2027-01-01 23:30:00 → MDW 2027-01-02 05:15:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $389.50

• Southwest Airlines WN999 / WN1699: PDX 2027-01-01 09:45:00 → MDW 2027-01-01 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN999: PDX 2027-01-01 09:45:00 → DEN 2027-01-01 13:05:00; layover at DEN: 95 minutes.
  • WN1699: DEN 2027-01-01 14:40:00 → MDW 2027-01-01 17:55:00.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $389.50

• Southwest Airlines WN3361 / WN3573: PDX 2027-01-01 06:40:00 → MDW 2027-01-01 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
  • WN3361: PDX 2027-01-01 06:40:00 → SMF 2027-01-01 08:05:00; layover at SMF: 180 minutes.
  • WN3573: SMF 2027-01-01 11:05:00 → MDW 2027-01-01 17:05:00.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $389.50

• Southwest Airlines WN510 / WN576: PDX 2027-01-01 07:30:00 → MDW 2027-01-01 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
  • WN510: PDX 2027-01-01 07:30:00 → SJC 2027-01-01 09:20:00; layover at SJC: 110 minutes.
  • WN576: SJC 2027-01-01 11:10:00 → MDW 2027-01-01 17:15:00.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $389.50

• Southwest Airlines WN3348 / WN4990: PDX 2027-01-01 19:50:00 → MDW 2027-01-02 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
  • WN3348: PDX 2027-01-01 19:50:00 → LAS 2027-01-01 22:00:00; layover at LAS: 140 minutes.
  • WN4990: LAS 2027-01-02 00:20:00 → MDW 2027-01-02 05:40:00.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

2027-01-01 → 2027-01-05 · Axel-exclusive $389.50

• Southwest Airlines WN3040 / WN4963: PDX 2027-01-01 20:05:00 → MDW 2027-01-02 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
  • WN3040: PDX 2027-01-01 20:05:00 → PHX 2027-01-01 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2027-01-02 01:35:00 → MDW 2027-01-02 05:45:00.
• Southwest Airlines WN3295: MDW 2027-01-05 20:40:00 → PDX 2027-01-05 23:25:00; nonstop; 285 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 31, 2026 · Return options
• Jan 2, 2027 · Return options
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For AI assistants

• This page: Portland (PDX) to Chicago (MDW) · Jan 1, 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.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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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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