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Portland → Chicago

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PDX → MDW1 adulteconomy

24 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW
Delta Air Lines
5:29 pmMDW
8h 17m
MSP · 2h 47m
11:46 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
5:45 amPDX
3h 45m
Nonstop
11:30 amMDW
Southwest Airlines
9:15 pmMDW
4h 40m
Nonstop
11:55 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:45 amPDX
3h 45m
Nonstop
11:30 amMDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
5:25 amPDX
3h 50m
Nonstop
11:15 amMDW
Southwest Airlines
2:35 pmMDW
8h 30m
LAS · 2h 10m
9:05 pmPDX

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:50 pmPDX
7h 50m
LAS · 2h 20m
5:40 am+1MDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:45 amPDX
6h 10m
DEN · 1h 35m
5:55 pmMDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:05 pmPDX
7h 40m
PHX · 2h
5:45 am+1MDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:40 amPDX
8h 25m
SMF · 3h
5:05 pmMDW
Southwest Airlines
10:00 amMDW
4h 35m
Nonstop
12:35 pmPDX

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
5:45 amPDX
3h 45m
Nonstop
11:30 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
11:20 pmPDX
8h 26m
DTW · 2h 40m
9:46 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:30 pmPDX
3h 45m
Nonstop
5:15 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:50 pmPDX
7h 50m
LAS · 2h 20m
5:40 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:45 amPDX
6h 10m
DEN · 1h 35m
5:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:05 pmPDX
7h 40m
PHX · 2h
5:45 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:40 amPDX
8h 25m
SMF · 3h
5:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:30 amPDX
7h 45m
SJC · 1h 50m
5:15 pmMDW

One-way 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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  • 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
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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 AirlinesWN507$185.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3350 / WN3295$350.002026-10-29T01:55:15Z
2026-11-20 · one wayDelta Air LinesDL411 + DL4684$210.002026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Delta Air LinesDL411 + DL4684 / DL4714 + DL2151$470.002026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN3350$185.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN507 / WN3295$350.002026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN507 / WN1045$411.252026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3350 / WN1045$411.252026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN3348 + WN4990$175.002026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN999 + WN1699$175.002026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN3040 + WN4963$175.002026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN3361 + WN3573$175.002026-10-29T01:55:15Z
2026-11-20 · one waySouthwest AirlinesWN510 + WN576$175.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3040 + WN4963 / WN3295$340.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3348 + WN4990 / WN3295$340.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN507 / WN3564 + WN2407$340.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3361 + WN3573 / WN3295$340.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN510 + WN576 / WN3295$340.002026-10-29T01:55:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN999 + WN1699 / WN3295$340.002026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN510 + WN576 / WN1045$397.752026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3348 + WN4990 / WN1045$397.752026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN999 + WN1699 / WN1045$397.752026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3040 + WN4963 / WN1045$397.752026-10-29T01:55:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3361 + WN3573 / WN1045$397.752026-10-29T01:55:15Z

2026-11-20 · one way · $185.00

  • Southwest Airlines WN507: PDX 2026-11-20 05:45:00 → MDW 2026-11-20 11:30:00; nonstop; 225 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $350.00

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

2026-11-20 · one way · $210.00

  • Delta Air Lines DL411 / DL4684: PDX 2026-11-20 23:20:00 → MDW 2026-11-21 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-11-20 23:20:00 → DTW 2026-11-21 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-11-21 09:10:00 → MDW 2026-11-21 09:46:00.

2026-11-27 → 2026-12-04 · $470.00

  • Delta Air Lines DL411 / DL4684: PDX 2026-11-27 23:20:00 → MDW 2026-11-28 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2026-11-27 23:20:00 → DTW 2026-11-28 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2026-11-28 09:10:00 → MDW 2026-11-28 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2026-12-04 17:29:00 → PDX 2026-12-04 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2026-12-04 17:29:00 → MSP 2026-12-04 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2026-12-04 21:59:00 → PDX 2026-12-04 23:46:00.

2026-11-20 · one way · $185.00

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

2026-11-20 → 2026-11-23 · $350.00

  • Southwest Airlines WN507: PDX 2026-11-20 05:45:00 → MDW 2026-11-20 11:30:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2026-11-23 21:15:00 → PDX 2026-11-23 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Southwest Airlines WN507: PDX 2026-11-27 05:45:00 → MDW 2026-11-27 11:30:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Southwest Airlines WN3350: PDX 2026-11-27 23:30:00 → MDW 2026-11-28 05:15:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3348 / WN4990: PDX 2026-11-20 19:50:00 → MDW 2026-11-21 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
    • WN3348: PDX 2026-11-20 19:50:00 → LAS 2026-11-20 22:00:00; layover at LAS: 140 minutes.
    • WN4990: LAS 2026-11-21 00:20:00 → MDW 2026-11-21 05:40:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN999 / WN1699: PDX 2026-11-20 09:45:00 → MDW 2026-11-20 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN999: PDX 2026-11-20 09:45:00 → DEN 2026-11-20 13:05:00; layover at DEN: 95 minutes.
    • WN1699: DEN 2026-11-20 14:40:00 → MDW 2026-11-20 17:55:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3040 / WN4963: PDX 2026-11-20 20:05:00 → MDW 2026-11-21 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
    • WN3040: PDX 2026-11-20 20:05:00 → PHX 2026-11-20 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-11-21 01:35:00 → MDW 2026-11-21 05:45:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3361 / WN3573: PDX 2026-11-20 06:40:00 → MDW 2026-11-20 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
    • WN3361: PDX 2026-11-20 06:40:00 → SMF 2026-11-20 08:05:00; layover at SMF: 180 minutes.
    • WN3573: SMF 2026-11-20 11:05:00 → MDW 2026-11-20 17:05:00.

2026-11-20 · one way · $175.00

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

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN3040 / WN4963: PDX 2026-11-20 20:05:00 → MDW 2026-11-21 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
    • WN3040: PDX 2026-11-20 20:05:00 → PHX 2026-11-20 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-11-21 01:35:00 → MDW 2026-11-21 05:45:00.
  • Southwest Airlines WN3295: MDW 2026-11-23 21:15:00 → PDX 2026-11-23 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN3348 / WN4990: PDX 2026-11-20 19:50:00 → MDW 2026-11-21 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
    • WN3348: PDX 2026-11-20 19:50:00 → LAS 2026-11-20 22:00:00; layover at LAS: 140 minutes.
    • WN4990: LAS 2026-11-21 00:20:00 → MDW 2026-11-21 05:40:00.
  • Southwest Airlines WN3295: MDW 2026-11-23 21:15:00 → PDX 2026-11-23 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN507: PDX 2026-11-20 05:25:00 → MDW 2026-11-20 11:15:00; nonstop; 230 minutes. Local airport times.
  • Southwest Airlines WN3564 / WN2407: MDW 2026-11-23 14:35:00 → PDX 2026-11-23 21:05:00; 1 stop(s) via LAS; 510 minutes. Local airport times.
    • WN3564: MDW 2026-11-23 14:35:00 → LAS 2026-11-23 16:30:00; layover at LAS: 130 minutes.
    • WN2407: LAS 2026-11-23 18:40:00 → PDX 2026-11-23 21:05:00.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN3361 / WN3573: PDX 2026-11-20 06:40:00 → MDW 2026-11-20 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
    • WN3361: PDX 2026-11-20 06:40:00 → SMF 2026-11-20 08:05:00; layover at SMF: 180 minutes.
    • WN3573: SMF 2026-11-20 11:05:00 → MDW 2026-11-20 17:05:00.
  • Southwest Airlines WN3295: MDW 2026-11-23 21:15:00 → PDX 2026-11-23 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.00

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

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN999 / WN1699: PDX 2026-11-20 09:45:00 → MDW 2026-11-20 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN999: PDX 2026-11-20 09:45:00 → DEN 2026-11-20 13:05:00; layover at DEN: 95 minutes.
    • WN1699: DEN 2026-11-20 14:40:00 → MDW 2026-11-20 17:55:00.
  • Southwest Airlines WN3295: MDW 2026-11-23 21:15:00 → PDX 2026-11-23 23:55:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $397.75

  • Southwest Airlines WN510 / WN576: PDX 2026-11-27 07:30:00 → MDW 2026-11-27 17:15:00; 1 stop(s) via SJC; 465 minutes. Local airport times.
    • WN510: PDX 2026-11-27 07:30:00 → SJC 2026-11-27 09:20:00; layover at SJC: 110 minutes.
    • WN576: SJC 2026-11-27 11:10:00 → MDW 2026-11-27 17:15:00.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $397.75

  • Southwest Airlines WN3348 / WN4990: PDX 2026-11-27 19:50:00 → MDW 2026-11-28 05:40:00; 1 stop(s) via LAS; 470 minutes. Local airport times.
    • WN3348: PDX 2026-11-27 19:50:00 → LAS 2026-11-27 22:00:00; layover at LAS: 140 minutes.
    • WN4990: LAS 2026-11-28 00:20:00 → MDW 2026-11-28 05:40:00.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $397.75

  • Southwest Airlines WN999 / WN1699: PDX 2026-11-27 09:45:00 → MDW 2026-11-27 17:55:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN999: PDX 2026-11-27 09:45:00 → DEN 2026-11-27 13:05:00; layover at DEN: 95 minutes.
    • WN1699: DEN 2026-11-27 14:40:00 → MDW 2026-11-27 17:55:00.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $397.75

  • Southwest Airlines WN3040 / WN4963: PDX 2026-11-27 20:05:00 → MDW 2026-11-28 05:45:00; 1 stop(s) via PHX; 460 minutes. Local airport times.
    • WN3040: PDX 2026-11-27 20:05:00 → PHX 2026-11-27 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-11-28 01:35:00 → MDW 2026-11-28 05:45:00.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $397.75

  • Southwest Airlines WN3361 / WN3573: PDX 2026-11-27 06:40:00 → MDW 2026-11-27 17:05:00; 1 stop(s) via SMF; 505 minutes. Local airport times.
    • WN3361: PDX 2026-11-27 06:40:00 → SMF 2026-11-27 08:05:00; layover at SMF: 180 minutes.
    • WN3573: SMF 2026-11-27 11:05:00 → MDW 2026-11-27 17:05:00.
  • Southwest Airlines WN1045: MDW 2026-12-04 10:00:00 → PDX 2026-12-04 12:35:00; nonstop; 275 minutes. Local airport times.

More dates for this route