Travel with Axel,
get the best price.

Chicago → Portland

Dec 7, 2026 · return Dec 9, 2026

MDW → PDX1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Mon, Dec 7 – Wed, Dec 9

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

Mon, Dec 7 – Wed, Dec 9

Southwest Airlines
8:40 pmMDW
4h 45m
Nonstop
11:25 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 7 – Wed, Dec 9

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX
Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Wed, Dec 9

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

Mon, Dec 7 – Wed, Dec 9

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

Mon, Dec 7 – Wed, Dec 9

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

Mon, Dec 7 – Wed, Dec 9

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

Mon, Dec 7 – Wed, Dec 9

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.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

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)
2026-12-07 → 2026-12-09Southwest AirlinesWN3295 / WN507$360.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN3295 / WN3350$360.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN3564 + WN2407 / WN510 + WN576$330.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN2995 + WN969 / WN510 + WN576$330.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN3174 + WN2916 / WN510 + WN576$330.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN4606 + WN1196 / WN510 + WN576$330.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN3035 + WN314 / WN510 + WN576$330.002026-10-29T01:29:13Z
2026-12-07 → 2026-12-09Southwest AirlinesWN3295 / WN510 + WN576$345.002026-10-29T01:29:13Z

2026-12-07 → 2026-12-09 · $360.00

  • Southwest Airlines WN3295: MDW 2026-12-07 10:05:00 → PDX 2026-12-07 12:40:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN507: PDX 2026-12-09 05:50:00 → MDW 2026-12-09 11:35:00; nonstop; 225 minutes. Local airport times.

2026-12-07 → 2026-12-09 · $360.00

  • Southwest Airlines WN3295: MDW 2026-12-07 20:40:00 → PDX 2026-12-07 23:25:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-09 23:30:00 → MDW 2026-12-10 05:15:00; nonstop; 225 minutes. Local airport times.

2026-12-07 → 2026-12-09 · $330.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-12-07 14:35:00 → PDX 2026-12-07 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-12-07 14:35:00 → LAS 2026-12-07 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-12-07 18:40:00 → PDX 2026-12-07 21:05:00.
  • Southwest Airlines WN510 / WN576: PDX 2026-12-09 07:30:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-09 07:30:00 → SJC 2026-12-09 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00.

2026-12-07 → 2026-12-09 · $330.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-12-07 05:05:00 → PDX 2026-12-07 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-07 05:05:00 → PHX 2026-12-07 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-12-07 09:00:00 → PDX 2026-12-07 10:50:00.
  • Southwest Airlines WN510 / WN576: PDX 2026-12-09 07:30:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-09 07:30:00 → SJC 2026-12-09 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00.

2026-12-07 → 2026-12-09 · $330.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-12-07 10:00:00 → PDX 2026-12-07 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-12-07 10:00:00 → OAK 2026-12-07 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-12-07 13:55:00 → PDX 2026-12-07 15:35:00.
  • Southwest Airlines WN510 / WN576: PDX 2026-12-09 07:30:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-09 07:30:00 → SJC 2026-12-09 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00.

2026-12-07 → 2026-12-09 · $330.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-12-07 14:35:00 → PDX 2026-12-07 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-12-07 14:35:00 → DEN 2026-12-07 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-12-07 18:25:00 → PDX 2026-12-07 20:15:00.
  • Southwest Airlines WN510 / WN576: PDX 2026-12-09 07:30:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-09 07:30:00 → SJC 2026-12-09 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00.

2026-12-07 → 2026-12-09 · $330.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-12-07 10:15:00 → PDX 2026-12-07 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-12-07 10:15:00 → SJC 2026-12-07 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-12-07 14:00:00 → PDX 2026-12-07 15:50:00.
  • Southwest Airlines WN510 / WN576: PDX 2026-12-09 07:30:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-12-09 07:30:00 → SJC 2026-12-09 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00.

2026-12-07 → 2026-12-09 · $345.00

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

More dates for this route