Travel with Axel,
get the best price.

Chicago → Portland

Choose your travel dates

MDW → PDX1 adulteconomy

24 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX
Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Show 8 more flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmMDW
7h 40m
DEN · 2h 10m
8:15 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
7h 35m
OAK · 1h 15m
3:35 pmPDX

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:15 amMDW
7h 35m
SJC · 1h
3:50 pmPDX

One-way 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.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. 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

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN3295$190.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3295 / WN3350$360.002026-10-29T01:29:13Z
2026-11-20 · one wayDelta Air LinesDL4714 + DL2151$210.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$390.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1045 / WN3350$423.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1045$190.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1045 / WN3350$360.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3295 / WN3350$423.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4606 + WN1196$175.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2995 + WN969$175.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3564 + WN2407$175.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3174 + WN2916$175.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3035 + WN314$175.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3035 + WN314 / WN3350$345.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4606 + WN1196 / WN3350$345.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2995 + WN969 / WN3350$345.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3174 + WN2916 / WN3350$345.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3564 + WN2407 / WN3350$345.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2995 + WN969 / WN3350$402.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3174 + WN2916 / WN3350$402.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3564 + WN2407 / WN3350$402.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4606 + WN1196 / WN3350$402.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3035 + WN314 / WN3350$402.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Delta Air LinesDL4714 + DL2151 / DL411 + DL4684$458.252026-10-29T01:29:13Z

2026-11-20 · one way · $190.00

  • Southwest Airlines WN3295: MDW 2026-11-20 21:15:00 → PDX 2026-11-20 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $360.00

  • Southwest Airlines WN3295: MDW 2026-11-20 21:15:00 → PDX 2026-11-20 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 · one way · $210.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-11-20 17:29:00 → PDX 2026-11-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-11-20 17:29:00 → MSP 2026-11-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-11-20 21:59:00 → PDX 2026-11-20 23:46:00.

2026-11-20 → 2026-11-23 · $390.00

  • Delta Air Lines DL4714 / DL2151: MDW 2026-11-20 17:29:00 → PDX 2026-11-20 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-11-20 17:29:00 → MSP 2026-11-20 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-11-20 21:59:00 → PDX 2026-11-20 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-11-23 23:20:00 → MDW 2026-11-24 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-11-23 23:20:00 → DTW 2026-11-24 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-11-24 09:10:00 → MDW 2026-11-24 09:46:00.

2026-11-27 → 2026-12-04 · $423.00

  • Southwest Airlines WN1045: MDW 2026-11-27 10:00:00 → PDX 2026-11-27 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 · one way · $190.00

  • Southwest Airlines WN1045: MDW 2026-11-20 10:00:00 → PDX 2026-11-20 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $360.00

  • Southwest Airlines WN1045: MDW 2026-11-20 10:00:00 → PDX 2026-11-20 12:35:00; nonstop; 275 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $423.00

  • Southwest Airlines WN3295: MDW 2026-11-27 21:15:00 → PDX 2026-11-27 23:55:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 · one way · $175.00

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

2026-11-20 · one way · $175.00

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

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-11-20 14:35:00 → PDX 2026-11-20 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-11-20 14:35:00 → LAS 2026-11-20 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-11-20 18:40:00 → PDX 2026-11-20 21:05:00.

2026-11-20 · one way · $175.00

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

2026-11-20 · one way · $175.00

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

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN3035 / WN314: MDW 2026-11-20 10:15:00 → PDX 2026-11-20 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-11-20 10:15:00 → SJC 2026-11-20 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-11-20 14:00:00 → PDX 2026-11-20 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN4606 / WN1196: MDW 2026-11-20 14:35:00 → PDX 2026-11-20 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-11-20 18:25:00 → PDX 2026-11-20 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN2995 / WN969: MDW 2026-11-20 05:05:00 → PDX 2026-11-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-11-20 05:05:00 → PHX 2026-11-20 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-11-20 09:00:00 → PDX 2026-11-20 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN3174 / WN2916: MDW 2026-11-20 10:00:00 → PDX 2026-11-20 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-11-20 10:00:00 → OAK 2026-11-20 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-11-20 13:55:00 → PDX 2026-11-20 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $345.00

  • Southwest Airlines WN3564 / WN2407: MDW 2026-11-20 14:35:00 → PDX 2026-11-20 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-11-20 14:35:00 → LAS 2026-11-20 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-11-20 18:40:00 → PDX 2026-11-20 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-11-23 23:30:00 → MDW 2026-11-24 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN2995 / WN969: MDW 2026-11-27 05:05:00 → PDX 2026-11-27 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-11-27 05:05:00 → PHX 2026-11-27 07:55:00; layover at PHX: 65 minutes.
    • WN969: PHX 2026-11-27 09:00:00 → PDX 2026-11-27 10:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN3174 / WN2916: MDW 2026-11-27 10:00:00 → PDX 2026-11-27 15:35:00; 1 stop(s) via OAK; 455 minutes. Local airport times.
    • WN3174: MDW 2026-11-27 10:00:00 → OAK 2026-11-27 12:40:00; layover at OAK: 75 minutes.
    • WN2916: OAK 2026-11-27 13:55:00 → PDX 2026-11-27 15:35:00.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN3564 / WN2407: MDW 2026-11-27 14:35:00 → PDX 2026-11-27 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-11-27 14:35:00 → LAS 2026-11-27 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-11-27 18:40:00 → PDX 2026-11-27 21:05:00.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN4606 / WN1196: MDW 2026-11-27 14:35:00 → PDX 2026-11-27 20:15:00; 1 stop(s) via DEN; 460 minutes. Local airport times.
    • WN4606: MDW 2026-11-27 14:35:00 → DEN 2026-11-27 16:15:00; layover at DEN: 130 minutes.
    • WN1196: DEN 2026-11-27 18:25:00 → PDX 2026-11-27 20:15:00.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $402.75

  • Southwest Airlines WN3035 / WN314: MDW 2026-11-27 10:15:00 → PDX 2026-11-27 15:50:00; 1 stop(s) via SJC; 455 minutes. Local airport times.
    • WN3035: MDW 2026-11-27 10:15:00 → SJC 2026-11-27 13:00:00; layover at SJC: 60 minutes.
    • WN314: SJC 2026-11-27 14:00:00 → PDX 2026-11-27 15:50:00.
  • Southwest Airlines WN3350: PDX 2026-12-04 23:30:00 → MDW 2026-12-05 05:15:00; nonstop; 225 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $458.25

  • Delta Air Lines DL4714 / DL2151: MDW 2026-11-27 17:29:00 → PDX 2026-11-27 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-11-27 17:29:00 → MSP 2026-11-27 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-11-27 21:59:00 → PDX 2026-11-27 23:46:00.
  • Delta Air Lines DL411 / DL4684: PDX 2026-12-04 23:20:00 → MDW 2026-12-05 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-12-04 23:20:00 → DTW 2026-12-05 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-12-05 09:10:00 → MDW 2026-12-05 09:46:00.

More dates for this route