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Chicago → Portland

Dec 16, 2026 · return Dec 21, 2026

MDW → PDX1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Wed, Dec 16 – Mon, Dec 21

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

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
10:10 amMDW
4h 35m
Nonstop
12:45 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 16 – Mon, Dec 21

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

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 5m
10:50 amPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Mon, Dec 21

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

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 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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)
2026-12-16 → 2026-12-21Southwest AirlinesWN3295 / WN3350$414.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$448.502026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN2087 / WN3350$414.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN3035 + WN314 / WN3350$399.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN3174 + WN2916 / WN3350$399.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN2995 + WN969 / WN3350$399.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN4606 + WN1196 / WN3350$399.002026-10-29T01:29:13Z
2026-12-16 → 2026-12-21Southwest AirlinesWN3564 + WN2407 / WN3350$399.002026-10-29T01:29:13Z

2026-12-16 → 2026-12-21 · $414.00

  • Southwest Airlines WN3295: MDW 2026-12-16 21:30:00 → PDX 2026-12-17 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $448.50

  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-16 17:29:00 → PDX 2026-12-16 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-16 17:29:00 → MSP 2026-12-16 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-16 21:59:00 → PDX 2026-12-16 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-21 23:20:00 → MDW 2026-12-22 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-21 23:20:00 → DTW 2026-12-22 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-22 09:10:00 → MDW 2026-12-22 09:46:00.

2026-12-16 → 2026-12-21 · $414.00

  • Southwest Airlines WN2087: MDW 2026-12-16 10:10:00 → PDX 2026-12-16 12:45:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $399.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-16 10:15:00 → PDX 2026-12-16 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-16 10:15:00 → SJC 2026-12-16 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-16 14:00:00 → PDX 2026-12-16 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $399.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-16 10:00:00 → PDX 2026-12-16 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-16 10:00:00 → OAK 2026-12-16 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-16 13:55:00 → PDX 2026-12-16 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $399.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-16 05:05:00 → PDX 2026-12-16 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-16 05:05:00 → PHX 2026-12-16 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-16 09:00:00 → PDX 2026-12-16 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $399.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-16 14:35:00 → PDX 2026-12-16 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-16 14:35:00 → DEN 2026-12-16 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-16 18:25:00 → PDX 2026-12-16 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-16 → 2026-12-21 · $399.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-16 14:35:00 → PDX 2026-12-16 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-16 14:35:00 → LAS 2026-12-16 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-16 18:40:00 → PDX 2026-12-16 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-21 23:30:00 → MDW 2026-12-22 05:15:00; nonstop; 225 minutes. Local airport times.

More dates for this route