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Route overview: Chicago to Portland (PDX) flight deals

Chicago → Portland

Jan 24, 2027 · return Feb 3, 2027

MDW → PDX1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
10:05 amMDW
4h 35m
Nonstop
12:40 pmPDX
Southwest Airlines
5:50 amPDX
3h 45m
Nonstop
11:35 amMDW

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1PDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Jan 24 – Wed, Feb 3

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

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Jan 24 – Wed, Feb 3

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

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ PDX

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 routeJan 23, 2027 → Feb 2, 2027Jan 25, 2027 → Feb 4, 2027
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: Chicago to Portland (PDX) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-24 → 2027-02-03Southwest AirlinesWN3295 / WN507$342.002026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$370.502026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN3295 / WN3350$342.002026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN3174 + WN2916 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN2995 + WN969 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN4606 + WN1196 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN3035 + WN314 / WN510 + WN576$313.502026-10-29T01:29:13Z
2027-01-24 → 2027-02-03Southwest AirlinesWN3295 / WN510 + WN576$327.752026-10-29T01:29:13Z

2027-01-24 → 2027-02-03 · $342.00

  • Southwest Airlines WN3295: MDW 2027-01-24 10:05:00 → PDX 2027-01-24 12:40:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN507: PDX 2027-02-03 05:50:00 → MDW 2027-02-03 11:35:00; nonstop; 225 minutes. Local airport times.

2027-01-24 → 2027-02-03 · $370.50

  • 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.
  • Delta Air Lines DL411 / DL4684: PDX 2027-02-03 23:20:00 → MDW 2027-02-04 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-02-03 23:20:00 → DTW 2027-02-04 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-02-04 09:10:00 → MDW 2027-02-04 09:46:00.

2027-01-24 → 2027-02-03 · $342.00

  • Southwest Airlines WN3295: MDW 2027-01-24 21:30:00 → PDX 2027-01-25 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2027-02-03 23:30:00 → MDW 2027-02-04 05:15:00; nonstop; 225 minutes. Local airport times.

2027-01-24 → 2027-02-03 · $313.50

  • 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.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-24 → 2027-02-03 · $313.50

  • 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.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-24 → 2027-02-03 · $313.50

  • 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.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-24 → 2027-02-03 · $313.50

  • 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.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

2027-01-24 → 2027-02-03 · $327.75

  • Southwest Airlines WN3295: MDW 2027-01-24 21:15:00 → PDX 2027-01-24 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN510 / WN576: PDX 2027-02-03 07:30:00 → MDW 2027-02-03 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2027-02-03 07:30:00 → SJC 2027-02-03 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2027-02-03 11:10:00 → MDW 2027-02-03 17:15:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Portland (PDX) · Jan 24, 2027 · return Feb 3, 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.
  • 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 Chicago to Portland (PDX) 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.