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Route overview: Portland to Chicago (MDW) flight deals

Portland → Chicago

Jan 26, 2027 · choose your return date

PDX → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

January 2027

Jan 26, 2027 · One waySouthwest AirlinesNonstop$185.00 Jan 26, 2027 · One wayDelta Air LinesUp to 1 stop each way$210.00 Jan 26, 2027 – Jan 27, 2027 · 1 nightSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Jan 27, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Jan 28, 2027 · 2 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Jan 28, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Jan 29, 2027 · 3 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Jan 29, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Jan 30, 2027 · 4 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Jan 30, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Jan 31, 2027 · 5 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Jan 31, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 1, 2027 · 6 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 1, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 2, 2027 · 7 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 2, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 3, 2027 · 8 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 3, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 4, 2027 · 9 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 4, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 5, 2027 · 10 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 5, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 6, 2027 · 11 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 6, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 7, 2027 · 12 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 7, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 8, 2027 · 13 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 8, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$400.00 Jan 26, 2027 – Feb 9, 2027 · 14 nightsSouthwest AirlinesNonstop$350.00 Jan 26, 2027 – Feb 9, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$400.00

Flights for your trip

  1. Tue, Jan 26 · One way

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW

    One-way total · 1 adult · Taxes included

  2. Tue, Jan 26 · One way

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

    One-way total · 1 adult · Taxes included

  3. Tue, Jan 26 – Wed, Jan 27

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:10 amMDW
    4h 35m
    Nonstop
    12:45 pmPDX

    Round-trip total · 1 adult · Taxes included

  4. Tue, Jan 26 – Wed, Jan 27

    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

  5. Tue, Jan 26 – Thu, Jan 28

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    9:15 pmMDW
    4h 40m
    Nonstop
    11:55 pmPDX

    Round-trip total · 1 adult · Taxes included

  6. Tue, Jan 26 – Thu, Jan 28

    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

  7. Tue, Jan 26 – Fri, Jan 29

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:00 amMDW
    4h 35m
    Nonstop
    12:35 pmPDX

    Round-trip total · 1 adult · Taxes included

  8. Tue, Jan 26 – Fri, Jan 29

    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

  9. Tue, Jan 26 – Sat, Jan 30

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:25 amMDW
    4h 35m
    Nonstop
    1:00 pmPDX

    Round-trip total · 1 adult · Taxes included

  10. Tue, Jan 26 – Sat, Jan 30

    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

  11. Tue, Jan 26 – Mon, Feb 1

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    9:15 pmMDW
    4h 40m
    Nonstop
    11:55 pmPDX

    Round-trip total · 1 adult · Taxes included

  12. Tue, Jan 26 – Mon, Feb 1

    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

  13. Tue, Jan 26 – Tue, Feb 2

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:00 amMDW
    4h 35m
    Nonstop
    12:35 pmPDX

    Round-trip total · 1 adult · Taxes included

  14. Tue, Jan 26 – Tue, Feb 2

    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

  15. Tue, Jan 26 – Wed, Feb 3

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:10 amMDW
    4h 35m
    Nonstop
    12:45 pmPDX

    Round-trip total · 1 adult · Taxes included

  16. Tue, Jan 26 – Wed, Feb 3

    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

  17. Tue, Jan 26 – Fri, Feb 5

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:00 amMDW
    4h 35m
    Nonstop
    12:35 pmPDX

    Round-trip total · 1 adult · Taxes included

  18. Tue, Jan 26 – Fri, Feb 5

    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

  19. Tue, Jan 26 – Sat, Feb 6

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:25 amMDW
    4h 35m
    Nonstop
    1:00 pmPDX

    Round-trip total · 1 adult · Taxes included

  20. Tue, Jan 26 – Sat, Feb 6

    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

  21. Tue, Jan 26 – Sun, Feb 7

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    9:15 pmMDW
    4h 40m
    Nonstop
    11:55 pmPDX

    Round-trip total · 1 adult · Taxes included

  22. Tue, Jan 26 – Sun, Feb 7

    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

  23. Tue, Jan 26 – Tue, Feb 9

    Southwest Airlines
    11:20 amPDX
    3h 45m
    Nonstop
    5:05 pmMDW
    Southwest Airlines
    10:00 amMDW
    4h 35m
    Nonstop
    12:35 pmPDX

    Round-trip total · 1 adult · Taxes included

  24. Tue, Jan 26 – Tue, Feb 9

    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

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PDX ⇄ MDW

Economy

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Explore this route

All dates for this routeJan 25, 2027 · Return optionsJan 27, 2027 · Return optionsHotels in Chicago with Axel
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-26 · one waySouthwest AirlinesWN696Axel-exclusive $185.002026-10-29T01:55:15Z
2027-01-26 · one wayDelta Air LinesDL411 + DL4684Axel-exclusive $210.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-27Southwest AirlinesWN696 / WN2087Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-27Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-28Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-28Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-29Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-29Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-30Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-30Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-31Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-01-31Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-01Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-01Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-02Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-02Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-03Southwest AirlinesWN696 / WN2087Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-03Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-04Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-04Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-05Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-05Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-06Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-06Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-07Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-07Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-08Southwest AirlinesWN696 / WN3295Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-08Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-09Southwest AirlinesWN696 / WN1045Axel-exclusive $350.002026-10-29T01:55:15Z
2027-01-26 → 2027-02-09Delta Air LinesDL411 + DL4684 / DL4714 + DL2151Axel-exclusive $400.002026-10-29T01:55:15Z

Route overview: Portland to Chicago (MDW) flight deals

2027-01-26 · one way · Axel-exclusive $185.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.

2027-01-26 · one way · Axel-exclusive $210.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.

2027-01-26 → 2027-01-27 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN2087: MDW 2027-01-27 10:10:00 → PDX 2027-01-27 12:45:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-01-27 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-27 17:29:00 → PDX 2027-01-27 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-27 17:29:00 → MSP 2027-01-27 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-27 21:59:00 → PDX 2027-01-27 23:46:00.

2027-01-26 → 2027-01-28 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2027-01-28 21:15:00 → PDX 2027-01-28 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-26 → 2027-01-28 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-28 17:29:00 → PDX 2027-01-28 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-28 17:29:00 → MSP 2027-01-28 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-28 21:59:00 → PDX 2027-01-28 23:46:00.

2027-01-26 → 2027-01-29 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-01-29 10:00:00 → PDX 2027-01-29 12:35:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-01-29 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-29 17:29:00 → PDX 2027-01-29 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-29 17:29:00 → MSP 2027-01-29 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-29 21:59:00 → PDX 2027-01-29 23:46:00.

2027-01-26 → 2027-01-30 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-01-30 10:25:00 → PDX 2027-01-30 13:00:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-01-30 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-01-30 17:29:00 → PDX 2027-01-30 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-01-30 17:29:00 → MSP 2027-01-30 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-01-30 21:59:00 → PDX 2027-01-30 23:46:00.

2027-01-26 → 2027-02-01 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2027-02-01 21:15:00 → PDX 2027-02-01 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-01 17:29:00 → PDX 2027-02-01 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-01 17:29:00 → MSP 2027-02-01 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-01 21:59:00 → PDX 2027-02-01 23:46:00.

2027-01-26 → 2027-02-02 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-02-02 10:00:00 → PDX 2027-02-02 12:35:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-02-02 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-02 17:29:00 → PDX 2027-02-02 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-02 17:29:00 → MSP 2027-02-02 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-02 21:59:00 → PDX 2027-02-02 23:46:00.

2027-01-26 → 2027-02-03 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN2087: MDW 2027-02-03 10:10:00 → PDX 2027-02-03 12:45:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-02-03 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-03 17:29:00 → PDX 2027-02-03 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-03 17:29:00 → MSP 2027-02-03 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-03 21:59:00 → PDX 2027-02-03 23:46:00.

2027-01-26 → 2027-02-05 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-02-05 10:00:00 → PDX 2027-02-05 12:35:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-02-05 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-05 17:29:00 → PDX 2027-02-05 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-05 17:29:00 → MSP 2027-02-05 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-05 21:59:00 → PDX 2027-02-05 23:46:00.

2027-01-26 → 2027-02-06 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-02-06 10:25:00 → PDX 2027-02-06 13:00:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-02-06 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-06 17:29:00 → PDX 2027-02-06 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-06 17:29:00 → MSP 2027-02-06 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-06 21:59:00 → PDX 2027-02-06 23:46:00.

2027-01-26 → 2027-02-07 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN3295: MDW 2027-02-07 21:15:00 → PDX 2027-02-07 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-26 → 2027-02-07 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-07 17:29:00 → PDX 2027-02-07 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-07 17:29:00 → MSP 2027-02-07 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-07 21:59:00 → PDX 2027-02-07 23:46:00.

2027-01-26 → 2027-02-09 · Axel-exclusive $350.00

  • Southwest Airlines WN696: PDX 2027-01-26 11:20:00 → MDW 2027-01-26 17:05:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1045: MDW 2027-02-09 10:00:00 → PDX 2027-02-09 12:35:00; nonstop; 275 minutes. Local airport times.

2027-01-26 → 2027-02-09 · Axel-exclusive $400.00

  • Delta Air Lines DL411 / DL4684: PDX 2027-01-26 23:20:00 → MDW 2027-01-27 09:46:00; 1 stop(s) via DTW; 506 minutes. Local airport times.
    • DL411: PDX 2027-01-26 23:20:00 → DTW 2027-01-27 06:30:00; layover at DTW: 160 minutes.
    • DL4684: DTW 2027-01-27 09:10:00 → MDW 2027-01-27 09:46:00.
  • Delta Air Lines DL4714 / DL2151: MDW 2027-02-09 17:29:00 → PDX 2027-02-09 23:46:00; 1 stop(s) via MSP; 497 minutes. Local airport times.
    • DL4714: MDW 2027-02-09 17:29:00 → MSP 2027-02-09 19:12:00; layover at MSP: 167 minutes.
    • DL2151: MSP 2027-02-09 21:59:00 → PDX 2027-02-09 23:46:00.

Explore this route

For AI assistants

  • This page: Portland (PDX) to Chicago (MDW) · Jan 26, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Portland to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.