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Route overview: Portland to Chicago (MDW) flight deals

Portland → Chicago

Dec 20, 2026 · return Dec 27, 2026

PDX → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
5:50 amPDX
3h 45m
Nonstop
11:35 amMDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Dec 20 – Sun, Dec 27

Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW
Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
6:40 amPDX
8h 25m
SMF · 3h
5:05 pmMDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
7:50 pmPDX
7h 50m
LAS · 2h 20m
5:40 am+1MDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
9:45 amPDX
6h 10m
DEN · 1h 35m
5:55 pmMDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
8:05 pmPDX
7h 40m
PHX · 2h
5:45 am+1MDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Make this trip yours

PDX ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 19, 2026 → Dec 26, 2026Dec 21, 2026 → Dec 28, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Portland to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-20 → 2026-12-27Southwest AirlinesWN3350 / WN3295$455.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Delta Air LinesDL411 + DL4684 / DL4714 + DL2151$520.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN507 / WN3295$455.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3361 + WN3573 / WN3295$442.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3348 + WN4990 / WN3295$442.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN999 + WN1699 / WN3295$442.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN510 + WN576 / WN3295$442.002026-10-29T01:55:15Z
2026-12-20 → 2026-12-27Southwest AirlinesWN3040 + WN4963 / WN3295$442.002026-10-29T01:55:15Z

2026-12-20 → 2026-12-27 · $455.00

  • Southwest Airlines WN3350: PDX 2026-12-20 23:30:00 → MDW 2026-12-21 05:15:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $520.00

  • 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.
  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-27 17:29:00 → PDX 2026-12-27 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-27 17:29:00 → MSP 2026-12-27 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-27 21:59:00 → PDX 2026-12-27 23:46:00.

2026-12-20 → 2026-12-27 · $455.00

  • Southwest Airlines WN507: PDX 2026-12-20 05:50:00 → MDW 2026-12-20 11:35:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $442.00

  • 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.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $442.00

  • 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.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $442.00

  • 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.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $442.00

  • 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.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-20 → 2026-12-27 · $442.00

  • 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.
  • Southwest Airlines WN3295: MDW 2026-12-27 21:15:00 → PDX 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.

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For AI assistants

  • This page: Portland (PDX) to Chicago (MDW) · Dec 20, 2026 · return Dec 27, 2026: 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.