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Route overview: Pittsburgh to Chicago (MDW) flight deals

Pittsburgh → Chicago

Dec 26, 2026 · choose your return date

PIT → 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.

December 2026

Dec 26, 2026 · One waySouthwest AirlinesNonstop$168.75 Dec 26, 2026 · One wayDelta Air LinesUp to 1 stop each way$231.25 Dec 26, 2026 – Dec 27, 2026 · 1 nightSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Dec 27, 2026 · 1 nightDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Dec 28, 2026 · 2 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Dec 28, 2026 · 2 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Dec 29, 2026 · 3 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Dec 29, 2026 · 3 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Dec 30, 2026 · 4 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Dec 30, 2026 · 4 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Dec 31, 2026 · 5 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Dec 31, 2026 · 5 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Jan 1, 2027 · 6 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Jan 1, 2027 · 6 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Jan 2, 2027 · 7 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Jan 2, 2027 · 7 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Jan 3, 2027 · 8 nightsSouthwest AirlinesNonstop$325.00 Dec 26, 2026 – Jan 3, 2027 · 8 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$381.25 Dec 26, 2026 – Jan 4, 2027 · 9 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 4, 2027 · 9 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75 Dec 26, 2026 – Jan 5, 2027 · 10 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 5, 2027 · 10 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75 Dec 26, 2026 – Jan 6, 2027 · 11 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 6, 2027 · 11 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75 Dec 26, 2026 – Jan 7, 2027 · 12 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 7, 2027 · 12 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75 Dec 26, 2026 – Jan 8, 2027 · 13 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 8, 2027 · 13 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75 Dec 26, 2026 – Jan 9, 2027 · 14 nightsSouthwest AirlinesNonstop$292.50 Dec 26, 2026 – Jan 9, 2027 · 14 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$348.75

Flights for your trip

  1. Sat, Dec 26 · One way

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW

    One-way total · 1 adult · Taxes included

  2. Sat, Dec 26 · One way

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW

    One-way total · 1 adult · Taxes included

  3. Sat, Dec 26 – Sun, Dec 27

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  4. Sat, Dec 26 – Sun, Dec 27

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  5. Sat, Dec 26 – Mon, Dec 28

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  6. Sat, Dec 26 – Mon, Dec 28

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  7. Sat, Dec 26 – Tue, Dec 29

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    8:15 amMDW
    1h 25m
    Nonstop
    10:40 amPIT

    Round-trip total · 1 adult · Taxes included

  8. Sat, Dec 26 – Tue, Dec 29

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    8:15 amMDW
    1h 25m
    Nonstop
    10:40 amPIT

    Round-trip total · 1 adult · Taxes included

  9. Sat, Dec 26 – Wed, Dec 30

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  10. Sat, Dec 26 – Wed, Dec 30

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  11. Sat, Dec 26 – Fri, Jan 1

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  12. Sat, Dec 26 – Fri, Jan 1

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  13. Sat, Dec 26 – Sat, Jan 2

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

  14. Sat, Dec 26 – Sat, Jan 2

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

  15. Sat, Dec 26 – Sun, Jan 3

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  16. Sat, Dec 26 – Sun, Jan 3

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  17. Sat, Dec 26 – Tue, Jan 5

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    8:15 amMDW
    1h 25m
    Nonstop
    10:40 amPIT

    Round-trip total · 1 adult · Taxes included

  18. Sat, Dec 26 – Tue, Jan 5

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    8:15 amMDW
    1h 25m
    Nonstop
    10:40 amPIT

    Round-trip total · 1 adult · Taxes included

  19. Sat, Dec 26 – Wed, Jan 6

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  20. Sat, Dec 26 – Wed, Jan 6

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  21. Sat, Dec 26 – Thu, Jan 7

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  22. Sat, Dec 26 – Thu, Jan 7

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

  23. Sat, Dec 26 – Sat, Jan 9

    Southwest Airlines
    8:45 amPIT
    1h 30m
    Nonstop
    9:15 amMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

  24. Sat, Dec 26 – Sat, Jan 9

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

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1 of 24

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PIT ⇄ MDW

Economy

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Explore this route

All dates for this routeDec 25, 2026 · Return optionsDec 27, 2026 · 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)
2026-12-26 · one waySouthwest AirlinesWN2313Axel-exclusive $168.752026-10-29T01:57:06Z
2026-12-26 · one wayDelta Air LinesDL5738 + DL4688Axel-exclusive $231.252026-10-29T01:57:06Z
2026-12-26 → 2026-12-27Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2026-12-27Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2026-12-28Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2026-12-28Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2026-12-29Southwest AirlinesWN2313 / WN3643Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2026-12-29Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2026-12-30Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2026-12-30Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2026-12-31Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2026-12-31Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2027-01-01Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2027-01-01Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2027-01-02Southwest AirlinesWN2313 / WN3004Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2027-01-02Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2027-01-03Southwest AirlinesWN2313 / WN3002Axel-exclusive $325.002026-10-29T01:57:06Z
2026-12-26 → 2027-01-03Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $381.252026-10-29T01:57:06Z
2026-12-26 → 2027-01-04Southwest AirlinesWN2313 / WN3002Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-04Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $348.752026-10-29T01:57:06Z
2026-12-26 → 2027-01-05Southwest AirlinesWN2313 / WN3643Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-05Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643Axel-exclusive $348.752026-10-29T01:57:06Z
2026-12-26 → 2027-01-06Southwest AirlinesWN2313 / WN3002Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-06Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $348.752026-10-29T01:57:06Z
2026-12-26 → 2027-01-07Southwest AirlinesWN2313 / WN3002Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-07Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $348.752026-10-29T01:57:06Z
2026-12-26 → 2027-01-08Southwest AirlinesWN2313 / WN3002Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-08Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $348.752026-10-29T01:57:06Z
2026-12-26 → 2027-01-09Southwest AirlinesWN2313 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-26 → 2027-01-09Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $348.752026-10-29T01:57:06Z

Route overview: Pittsburgh to Chicago (MDW) flight deals

2026-12-26 · one way · Axel-exclusive $168.75

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $231.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.

2026-12-26 → 2026-12-27 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-27 07:45:00 → PIT 2026-12-27 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2026-12-27 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-12-27 07:45:00 → PIT 2026-12-27 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2026-12-28 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-28 07:45:00 → PIT 2026-12-28 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2026-12-28 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-12-28 07:45:00 → PIT 2026-12-28 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2026-12-29 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2026-12-29 08:15:00 → PIT 2026-12-29 10:40:00; nonstop; 85 minutes. Local airport times.

2026-12-26 → 2026-12-29 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3643: MDW 2026-12-29 08:15:00 → PIT 2026-12-29 10:40:00; nonstop; 85 minutes. Local airport times.

2026-12-26 → 2026-12-30 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-30 07:45:00 → PIT 2026-12-30 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2026-12-30 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-12-30 07:45:00 → PIT 2026-12-30 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-01 07:45:00 → PIT 2027-01-01 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-01-01 07:45:00 → PIT 2027-01-01 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-01-02 18:55:00 → PIT 2027-01-02 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3004: MDW 2027-01-02 18:55:00 → PIT 2027-01-02 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $325.00

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-03 07:45:00 → PIT 2027-01-03 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $381.25

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-01-03 07:45:00 → PIT 2027-01-03 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-05 · Axel-exclusive $292.50

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2027-01-05 08:15:00 → PIT 2027-01-05 10:40:00; nonstop; 85 minutes. Local airport times.

2026-12-26 → 2027-01-05 · Axel-exclusive $348.75

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3643: MDW 2027-01-05 08:15:00 → PIT 2027-01-05 10:40:00; nonstop; 85 minutes. Local airport times.

2026-12-26 → 2027-01-06 · Axel-exclusive $292.50

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-06 07:45:00 → PIT 2027-01-06 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-06 · Axel-exclusive $348.75

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-01-06 07:45:00 → PIT 2027-01-06 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-07 · Axel-exclusive $292.50

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-07 07:45:00 → PIT 2027-01-07 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-07 · Axel-exclusive $348.75

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-01-07 07:45:00 → PIT 2027-01-07 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $292.50

  • Southwest Airlines WN2313: PIT 2026-12-26 08:45:00 → MDW 2026-12-26 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-01-09 18:55:00 → PIT 2027-01-09 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $348.75

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-26 10:31:00 → MDW 2026-12-26 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-26 10:31:00 → DTW 2026-12-26 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-26 12:44:00 → MDW 2026-12-26 13:01:00.
  • Southwest Airlines WN3004: MDW 2027-01-09 18:55:00 → PIT 2027-01-09 21:25:00; nonstop; 90 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Pittsburgh (PIT) to Chicago (MDW) · Dec 26, 2026 · 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 Pittsburgh 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.