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Portland → Chicago

Dec 28, 2026 · return Dec 31, 2026

PDX → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

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

Mon, Dec 28 – Thu, Dec 31

Southwest Airlines
5:45 amPDX
3h 45m
Nonstop
11:30 amMDW
Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 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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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)
2026-12-28 → 2026-12-31Southwest AirlinesWN3350 / WN3295$455.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN507 / WN3295$455.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN510 + WN576 / WN3295$442.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN3348 + WN4990 / WN3295$442.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN3361 + WN3573 / WN3295$442.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN3040 + WN4963 / WN3295$442.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN999 + WN1699 / WN3295$442.002026-10-29T01:55:15Z
2026-12-28 → 2026-12-31Southwest AirlinesWN507 / WN4606 + WN1196$442.002026-10-29T01:55:15Z

2026-12-28 → 2026-12-31 · $455.00

  • Southwest Airlines WN3350: PDX 2026-12-28 23:30:00 → MDW 2026-12-29 05:15:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $455.00

  • Southwest Airlines WN507: PDX 2026-12-28 05:50:00 → MDW 2026-12-28 11:35:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN510 / WN576: PDX 2026-12-28 07:30:00 → MDW 2026-12-28 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-28 07:30:00 → SJC 2026-12-28 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-28 11:10:00 → MDW 2026-12-28 17:15:00.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN3348 / WN4990: PDX 2026-12-28 19:50:00 → MDW 2026-12-29 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
    • WN3348: PDX 2026-12-28 19:50:00 → LAS 2026-12-28 22:00:00; layover at LAS: 140 minutes.
    • WN4990: LAS 2026-12-29 00:20:00 → MDW 2026-12-29 05:40:00.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN3361 / WN3573: PDX 2026-12-28 06:40:00 → MDW 2026-12-28 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
    • WN3361: PDX 2026-12-28 06:40:00 → SMF 2026-12-28 08:05:00; layover at SMF: 180 minutes.
    • WN3573: SMF 2026-12-28 11:05:00 → MDW 2026-12-28 17:05:00.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN3040 / WN4963: PDX 2026-12-28 20:05:00 → MDW 2026-12-29 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
    • WN3040: PDX 2026-12-28 20:05:00 → PHX 2026-12-28 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-29 01:35:00 → MDW 2026-12-29 05:45:00.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN999 / WN1699: PDX 2026-12-28 09:45:00 → MDW 2026-12-28 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN999: PDX 2026-12-28 09:45:00 → DEN 2026-12-28 13:05:00; layover at DEN: 95 minutes.
    • WN1699: DEN 2026-12-28 14:40:00 → MDW 2026-12-28 17:55:00.
  • Southwest Airlines WN3295: MDW 2026-12-31 21:15:00 → PDX 2026-12-31 23:55:00; nonstop; 280 minutes. Local airport times.

2026-12-28 → 2026-12-31 · $442.00

  • Southwest Airlines WN507: PDX 2026-12-28 05:45:00 → MDW 2026-12-28 11:30:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-31 14:35:00 → PDX 2026-12-31 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-31 14:35:00 → DEN 2026-12-31 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-31 18:25:00 → PDX 2026-12-31 20:15:00.

More dates for this route