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Chicago → Portland

Jan 19, 2027 · return Feb 2, 2027

MDW → PDX1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
8:40 pmMDW
4h 45m
Nonstop
11:25 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Tue, Jan 19 – Tue, Feb 2

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

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Jan 19 – Tue, Feb 2

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:20 amPDX
3h 45m
Nonstop
5:05 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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More dates

All dates for this routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-19 → 2027-02-02Southwest AirlinesWN1045 / WN696$342.002026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$370.502026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN3295 / WN696$342.002026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN3564 + WN2407 / WN696$327.752026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN4606 + WN1196 / WN696$327.752026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN3174 + WN2916 / WN696$327.752026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN3035 + WN314 / WN696$327.752026-10-29T01:29:13Z
2027-01-19 → 2027-02-02Southwest AirlinesWN2995 + WN969 / WN696$327.752026-10-29T01:29:13Z

2027-01-19 → 2027-02-02 · $342.00

  • Southwest Airlines WN1045: MDW 2027-01-19 10:00:00 → PDX 2027-01-19 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $370.50

  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-19 17:29:00 → PDX 2027-01-19 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-19 17:29:00 → MSP 2027-01-19 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-19 21:59:00 → PDX 2027-01-19 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2027-02-02 23:20:00 → MDW 2027-02-03 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-02-02 23:20:00 → DTW 2027-02-03 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-02-03 09:10:00 → MDW 2027-02-03 09:46:00.

2027-01-19 → 2027-02-02 · $342.00

  • Southwest Airlines WN3295: MDW 2027-01-19 20:40:00 → PDX 2027-01-19 23:25:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $327.75

  • Southwest Airlines WN3564 / WN2407: MDW 2027-01-19 14:35:00 → PDX 2027-01-19 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2027-01-19 14:35:00 → LAS 2027-01-19 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2027-01-19 18:40:00 → PDX 2027-01-19 21:05:00.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $327.75

  • Southwest Airlines WN4606 / WN1196: MDW 2027-01-19 14:35:00 → PDX 2027-01-19 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2027-01-19 14:35:00 → DEN 2027-01-19 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2027-01-19 18:25:00 → PDX 2027-01-19 20:15:00.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $327.75

  • Southwest Airlines WN3174 / WN2916: MDW 2027-01-19 10:00:00 → PDX 2027-01-19 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2027-01-19 10:00:00 → OAK 2027-01-19 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2027-01-19 13:55:00 → PDX 2027-01-19 15:35:00.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $327.75

  • Southwest Airlines WN3035 / WN314: MDW 2027-01-19 10:15:00 → PDX 2027-01-19 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2027-01-19 10:15:00 → SJC 2027-01-19 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2027-01-19 14:00:00 → PDX 2027-01-19 15:50:00.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-19 → 2027-02-02 · $327.75

  • Southwest Airlines WN2995 / WN969: MDW 2027-01-19 05:05:00 → PDX 2027-01-19 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2027-01-19 05:05:00 → PHX 2027-01-19 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2027-01-19 09:00:00 → PDX 2027-01-19 10:50:00.
  • Southwest Airlines WN696: PDX 2027-02-02 11:20:00 → MDW 2027-02-02 17:05:00; nonstop; 225 minutes. Local airport times.

More dates for this route