Portland (PDX) to Chicago (MDW) · Nov 23, 2026 · return Dec 7, 2026

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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Nov 23 – Dec 7, 2026 · 14 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $1,725 total · 4★ The Royal Sonesta Chicago River North, $2,479 total · 5★ Nobu Hotel Chicago, $5,329.50 total

All hotels in Chicago

Route overview: Portland to Chicago (MDW) flight deals

2026-11-23 → 2026-12-07 · Axel-exclusive $350.00

• Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-23 → 2026-12-07 · Axel-exclusive $400.00

• Delta Air Lines DL411 / DL4684: PDX 2026-11-23 23:20:00 → MDW 2026-11-24 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
  • DL411: PDX 2026-11-23 23:20:00 → DTW 2026-11-24 06:30:00; layover at DTW: 160 minutes.
  • DL4684: DTW 2026-11-24 09:10:00 → MDW 2026-11-24 09:46:00.
• Delta Air Lines DL4714 / DL2151: MDW 2026-12-07 17:29:00 → PDX 2026-12-07 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
  • DL4714: MDW 2026-12-07 17:29:00 → MSP 2026-12-07 19:12:00; layover at MSP: 167 minutes.
  • DL2151: MSP 2026-12-07 21:59:00 → PDX 2026-12-07 23:46:00.

2026-11-23 → 2026-12-07 · Axel-exclusive $350.00

• Southwest Airlines WN507: PDX 2026-11-23 05:50:00 → MDW 2026-11-23 11:35:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-23 → 2026-12-07 · Axel-exclusive $340.00

• Southwest Airlines WN3348 / WN4990: PDX 2026-11-23 19:50:00 → MDW 2026-11-24 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
  • WN3348: PDX 2026-11-23 19:50:00 → LAS 2026-11-23 22:00:00; layover at LAS: 140 minutes.
  • WN4990: LAS 2026-11-24 00:20:00 → MDW 2026-11-24 05:40:00.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-23 → 2026-12-07 · Axel-exclusive $340.00

• Southwest Airlines WN510 / WN576: PDX 2026-11-23 07:30:00 → MDW 2026-11-23 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
  • WN510: PDX 2026-11-23 07:30:00 → SJC 2026-11-23 09:20:00; layover at SJC: 110 minutes.
  • WN576: SJC 2026-11-23 11:10:00 → MDW 2026-11-23 17:15:00.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-23 → 2026-12-07 · Axel-exclusive $340.00

• Southwest Airlines WN999 / WN1699: PDX 2026-11-23 09:45:00 → MDW 2026-11-23 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN999: PDX 2026-11-23 09:45:00 → DEN 2026-11-23 13:05:00; layover at DEN: 95 minutes.
  • WN1699: DEN 2026-11-23 14:40:00 → MDW 2026-11-23 17:55:00.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-23 → 2026-12-07 · Axel-exclusive $340.00

• Southwest Airlines WN507: PDX 2026-11-23 06:00:00 → MDW 2026-11-23 11:50:00; nonstop; 230 minutes. Local airport times.
• Southwest Airlines WN3564 / WN2407: MDW 2026-12-07 14:35:00 → PDX 2026-12-07 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
  • WN3564: MDW 2026-12-07 14:35:00 → LAS 2026-12-07 16:30:00; layover at LAS: 130 minutes.
  • WN2407: LAS 2026-12-07 18:40:00 → PDX 2026-12-07 21:05:00.

2026-11-23 → 2026-12-07 · Axel-exclusive $340.00

• Southwest Airlines WN3361 / WN3573: PDX 2026-11-23 06:40:00 → MDW 2026-11-23 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
  • WN3361: PDX 2026-11-23 06:40:00 → SMF 2026-11-23 08:05:00; layover at SMF: 180 minutes.
  • WN3573: SMF 2026-11-23 11:05:00 → MDW 2026-11-23 17:05:00.
• Southwest Airlines WN3295: MDW 2026-12-07 21:15:00 → PDX 2026-12-07 23:55:00; nonstop; 280 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 22, 2026 · Return options
• Nov 24, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (MDW) · Nov 23, 2026 · return Dec 7, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• 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.

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