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Route overview: Pittsburgh to Chicago (MDW) flight deals

Pittsburgh → Chicago

May 29, 2027 · 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.

May 2027

May 29, 2027 · One waySouthwest AirlinesNonstop$178.25 May 29, 2027 · One wayDelta Air LinesUp to 1 stop each way$235.75 May 29, 2027 – May 30, 2027 · 1 nightSouthwest AirlinesNonstop$345.00 May 29, 2027 – May 30, 2027 · 1 nightDelta Air Lines / Southwest AirlinesUp to 1 stop each way$396.75 May 29, 2027 – May 31, 2027 · 2 nightsSouthwest AirlinesNonstop$345.00 May 29, 2027 – May 31, 2027 · 2 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$396.75 May 29, 2027 – Jun 1, 2027 · 3 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 1, 2027 · 3 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 2, 2027 · 4 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 2, 2027 · 4 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 3, 2027 · 5 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 3, 2027 · 5 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 4, 2027 · 6 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 4, 2027 · 6 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 5, 2027 · 7 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 5, 2027 · 7 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 6, 2027 · 8 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 6, 2027 · 8 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 7, 2027 · 9 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 7, 2027 · 9 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 8, 2027 · 10 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 8, 2027 · 10 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 9, 2027 · 11 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 9, 2027 · 11 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 10, 2027 · 12 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 10, 2027 · 12 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 11, 2027 · 13 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 11, 2027 · 13 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25 May 29, 2027 – Jun 12, 2027 · 14 nightsSouthwest AirlinesNonstop$322.50 May 29, 2027 – Jun 12, 2027 · 14 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$374.25

Flights for your trip

  1. Sat, May 29 · One way

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

    One-way total · 1 adult · Taxes included

  2. Sat, May 29 · One way

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

    One-way total · 1 adult · Taxes included

  3. Sat, May 29 – Sun, May 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

  4. Sat, May 29 – Sun, May 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

  5. Sat, May 29 – Mon, May 31

    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, May 29 – Mon, May 31

    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, May 29 – Tue, Jun 1

    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, May 29 – Tue, Jun 1

    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, May 29 – Wed, Jun 2

    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, May 29 – Wed, Jun 2

    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, May 29 – Fri, Jun 4

    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, May 29 – Fri, Jun 4

    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, May 29 – Sat, Jun 5

    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, May 29 – Sat, Jun 5

    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, May 29 – Sun, Jun 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

  16. Sat, May 29 – Sun, Jun 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

  17. Sat, May 29 – Tue, Jun 8

    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, May 29 – Tue, Jun 8

    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, May 29 – Wed, Jun 9

    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, May 29 – Wed, Jun 9

    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, May 29 – Thu, Jun 10

    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, May 29 – Thu, Jun 10

    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, May 29 – Sat, Jun 12

    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, May 29 – Sat, Jun 12

    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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PIT ⇄ MDW

Economy

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Explore this route

All dates for this routeMay 28, 2027 · Return optionsMay 30, 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)
2027-05-29 · one waySouthwest AirlinesWN2313Axel-exclusive $178.252026-10-29T01:57:06Z
2027-05-29 · one wayDelta Air LinesDL5738 + DL4688Axel-exclusive $235.752026-10-29T01:57:06Z
2027-05-29 → 2027-05-30Southwest AirlinesWN2313 / WN3002Axel-exclusive $345.002026-10-29T01:57:06Z
2027-05-29 → 2027-05-30Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $396.752026-10-29T01:57:06Z
2027-05-29 → 2027-05-31Southwest AirlinesWN2313 / WN3002Axel-exclusive $345.002026-10-29T01:57:06Z
2027-05-29 → 2027-05-31Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $396.752026-10-29T01:57:06Z
2027-05-29 → 2027-06-01Southwest AirlinesWN2313 / WN3643Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-01Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-02Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-02Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-03Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-03Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-04Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-04Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-05Southwest AirlinesWN2313 / WN3004Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-05Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-06Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-06Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-07Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-07Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-08Southwest AirlinesWN2313 / WN3643Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-08Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-09Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-09Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-10Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-10Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-11Southwest AirlinesWN2313 / WN3002Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-11Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $374.252026-10-29T01:57:06Z
2027-05-29 → 2027-06-12Southwest AirlinesWN2313 / WN3004Axel-exclusive $322.502026-10-29T01:57:06Z
2027-05-29 → 2027-06-12Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $374.252026-10-29T01:57:06Z

Route overview: Pittsburgh to Chicago (MDW) flight deals

2027-05-29 · one way · Axel-exclusive $178.25

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.

2027-05-29 · one way · Axel-exclusive $235.75

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.

2027-05-29 → 2027-05-30 · Axel-exclusive $345.00

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-05-30 07:45:00 → PIT 2027-05-30 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-05-30 · Axel-exclusive $396.75

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-05-30 07:45:00 → PIT 2027-05-30 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-05-31 · Axel-exclusive $345.00

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-05-31 07:45:00 → PIT 2027-05-31 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-05-31 · Axel-exclusive $396.75

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-05-31 07:45:00 → PIT 2027-05-31 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-01 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2027-06-01 08:15:00 → PIT 2027-06-01 10:40:00; nonstop; 85 minutes. Local airport times.

2027-05-29 → 2027-06-01 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3643: MDW 2027-06-01 08:15:00 → PIT 2027-06-01 10:40:00; nonstop; 85 minutes. Local airport times.

2027-05-29 → 2027-06-02 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-06-02 07:45:00 → PIT 2027-06-02 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-02 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-06-02 07:45:00 → PIT 2027-06-02 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-04 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-06-04 07:45:00 → PIT 2027-06-04 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-04 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-06-04 07:45:00 → PIT 2027-06-04 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-05 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-06-05 18:55:00 → PIT 2027-06-05 21:25:00; nonstop; 90 minutes. Local airport times.

2027-05-29 → 2027-06-05 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3004: MDW 2027-06-05 18:55:00 → PIT 2027-06-05 21:25:00; nonstop; 90 minutes. Local airport times.

2027-05-29 → 2027-06-06 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-06-06 07:45:00 → PIT 2027-06-06 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-06 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-06-06 07:45:00 → PIT 2027-06-06 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-08 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2027-06-08 08:15:00 → PIT 2027-06-08 10:40:00; nonstop; 85 minutes. Local airport times.

2027-05-29 → 2027-06-08 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3643: MDW 2027-06-08 08:15:00 → PIT 2027-06-08 10:40:00; nonstop; 85 minutes. Local airport times.

2027-05-29 → 2027-06-09 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-06-09 07:45:00 → PIT 2027-06-09 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-09 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-06-09 07:45:00 → PIT 2027-06-09 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-10 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-06-10 07:45:00 → PIT 2027-06-10 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-10 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-06-10 07:45:00 → PIT 2027-06-10 10:05:00; nonstop; 80 minutes. Local airport times.

2027-05-29 → 2027-06-12 · Axel-exclusive $322.50

  • Southwest Airlines WN2313: PIT 2027-05-29 08:45:00 → MDW 2027-05-29 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-06-12 18:55:00 → PIT 2027-06-12 21:25:00; nonstop; 90 minutes. Local airport times.

2027-05-29 → 2027-06-12 · Axel-exclusive $374.25

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-29 10:31:00 → MDW 2027-05-29 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-29 10:31:00 → DTW 2027-05-29 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-29 12:44:00 → MDW 2027-05-29 13:01:00.
  • Southwest Airlines WN3004: MDW 2027-06-12 18:55:00 → PIT 2027-06-12 21:25:00; nonstop; 90 minutes. Local airport times.

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For AI assistants

  • This page: Pittsburgh (PIT) to Chicago (MDW) · May 29, 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 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.