Portland (PDX) to Chicago (MDW) · Dec 20, 2026 · 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: Portland to Chicago (MDW) flight deals

2026-12-20 · one way · Axel-exclusive $240.50

• Southwest Airlines WN507: PDX 2026-12-20 05:25:00 → MDW 2026-12-20 11:15:00; nonstop; 230 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $273.00

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

2026-12-20 · one way · Axel-exclusive $240.50

• Southwest Airlines WN3350: PDX 2026-12-20 23:30:00 → MDW 2026-12-21 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $227.50

• Southwest Airlines WN510 / WN576: PDX 2026-12-20 07:30:00 → MDW 2026-12-20 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
  • WN510: PDX 2026-12-20 07:30:00 → SJC 2026-12-20 09:20:00; layover at SJC: 110 minutes.
  • WN576: SJC 2026-12-20 11:10:00 → MDW 2026-12-20 17:15:00.

2026-12-20 · one way · Axel-exclusive $227.50

• Southwest Airlines WN3040 / WN4963: PDX 2026-12-20 20:05:00 → MDW 2026-12-21 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
  • WN3040: PDX 2026-12-20 20:05:00 → PHX 2026-12-20 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2026-12-21 01:35:00 → MDW 2026-12-21 05:45:00.

2026-12-20 · one way · Axel-exclusive $227.50

• Southwest Airlines WN999 / WN1699: PDX 2026-12-20 09:45:00 → MDW 2026-12-20 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN999: PDX 2026-12-20 09:45:00 → DEN 2026-12-20 13:05:00; layover at DEN: 95 minutes.
  • WN1699: DEN 2026-12-20 14:40:00 → MDW 2026-12-20 17:55:00.

2026-12-20 · one way · Axel-exclusive $227.50

• Southwest Airlines WN3348 / WN4990: PDX 2026-12-20 19:50:00 → MDW 2026-12-21 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
  • WN3348: PDX 2026-12-20 19:50:00 → LAS 2026-12-20 22:00:00; layover at LAS: 140 minutes.
  • WN4990: LAS 2026-12-21 00:20:00 → MDW 2026-12-21 05:40:00.

2026-12-20 · one way · Axel-exclusive $227.50

• Southwest Airlines WN3361 / WN3573: PDX 2026-12-20 06:40:00 → MDW 2026-12-20 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
  • WN3361: PDX 2026-12-20 06:40:00 → SMF 2026-12-20 08:05:00; layover at SMF: 180 minutes.
  • WN3573: SMF 2026-12-20 11:05:00 → MDW 2026-12-20 17:05:00.

Explore this route

• All dates for this route
• Dec 19, 2026 · Return options
• Dec 21, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (MDW) · Dec 20, 2026 · one way: 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Portland to Chicago (MDW) flight deals · Flight search guide.
• 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.

Feedback (optional): Missing info · Axel issue