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Route overview: Pittsburgh to Chicago (MDW) flight deals

Pittsburgh → Chicago

Dec 10, 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 10, 2026 · One waySouthwest AirlinesNonstop$135.00 Dec 10, 2026 · One wayDelta Air LinesUp to 1 stop each way$185.00 Dec 10, 2026 – Dec 11, 2026 · 1 nightSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 11, 2026 · 1 nightDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 12, 2026 · 2 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 12, 2026 · 2 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 13, 2026 · 3 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 13, 2026 · 3 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 14, 2026 · 4 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 14, 2026 · 4 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 15, 2026 · 5 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 15, 2026 · 5 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 16, 2026 · 6 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 16, 2026 · 6 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 17, 2026 · 7 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 17, 2026 · 7 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 18, 2026 · 8 nightsSouthwest AirlinesNonstop$260.00 Dec 10, 2026 – Dec 18, 2026 · 8 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$305.00 Dec 10, 2026 – Dec 19, 2026 · 9 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 19, 2026 · 9 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50 Dec 10, 2026 – Dec 20, 2026 · 10 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 20, 2026 · 10 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50 Dec 10, 2026 – Dec 21, 2026 · 11 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 21, 2026 · 11 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50 Dec 10, 2026 – Dec 22, 2026 · 12 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 22, 2026 · 12 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50 Dec 10, 2026 – Dec 23, 2026 · 13 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 23, 2026 · 13 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50 Dec 10, 2026 – Dec 24, 2026 · 14 nightsSouthwest AirlinesNonstop$292.50 Dec 10, 2026 – Dec 24, 2026 · 14 nightsDelta Air Lines / Southwest AirlinesUp to 1 stop each way$337.50

Flights for your trip

  1. Thu, Dec 10 · One way

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Thu, Dec 10 · One way

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

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Thu, Dec 10 – Fri, Dec 11

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    8:15 amMDW
    1h 25m
    Nonstop
    10:40 amPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Thu, Dec 10 – Fri, Dec 11

    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

    Availability is checked when you select these flights.

  5. Thu, Dec 10 – Sat, Dec 12

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Thu, Dec 10 – Sat, Dec 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

    Availability is checked when you select these flights.

  7. Thu, Dec 10 – Sun, Dec 13

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:50 pmMDW
    1h 30m
    Nonstop
    9:20 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Thu, Dec 10 – Sun, Dec 13

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:50 pmMDW
    1h 30m
    Nonstop
    9:20 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  9. Thu, Dec 10 – Mon, Dec 14

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Thu, Dec 10 – Mon, Dec 14

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  11. Thu, Dec 10 – Wed, Dec 16

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Thu, Dec 10 – Wed, Dec 16

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  13. Thu, Dec 10 – Thu, Dec 17

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Thu, Dec 10 – Thu, Dec 17

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  15. Thu, Dec 10 – Fri, Dec 18

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Thu, Dec 10 – Fri, Dec 18

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  17. Thu, Dec 10 – Sun, Dec 20

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    7:45 amMDW
    1h 20m
    Nonstop
    10:05 amPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Thu, Dec 10 – Sun, Dec 20

    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

    Availability is checked when you select these flights.

  19. Thu, Dec 10 – Mon, Dec 21

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Thu, Dec 10 – Mon, Dec 21

    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

    Availability is checked when you select these flights.

  21. Thu, Dec 10 – Tue, Dec 22

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Thu, Dec 10 – Tue, Dec 22

    Delta Air Lines
    10:31 amPIT
    3h 30m
    DTW · 1h
    1:01 pmMDW
    Southwest Airlines
    6:10 pmMDW
    1h 35m
    Nonstop
    8:45 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  23. Thu, Dec 10 – Thu, Dec 24

    Southwest Airlines
    7:25 pmPIT
    1h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:55 pmMDW
    1h 30m
    Nonstop
    9:25 pmPIT

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Thu, Dec 10 – Thu, Dec 24

    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

    Availability is checked when you select these flights.

Swipe to see 23 more recent deals.

1 of 24

Make this trip yours

PIT ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 9, 2026 · Return optionsDec 11, 2026 · Return optionsHotels in Chicago with Axel
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.

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)
2026-12-10 · one waySouthwest AirlinesWN3556Axel-exclusive $135.002026-10-29T01:57:06Z
2026-12-10 · one wayDelta Air LinesDL5738 + DL4688Axel-exclusive $185.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-11Southwest AirlinesWN3556 / WN3643Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-11Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-12Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-12Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-13Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-13Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-14Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-14Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-15Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-15Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-16Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-16Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-17Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-17Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-18Southwest AirlinesWN3556 / WN3004Axel-exclusive $260.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-18Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $305.002026-10-29T01:57:06Z
2026-12-10 → 2026-12-19Southwest AirlinesWN3556 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-19Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $337.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-20Southwest AirlinesWN3556 / WN3002Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-20Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002Axel-exclusive $337.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-21Southwest AirlinesWN3556 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-21Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $337.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-22Southwest AirlinesWN3556 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-22Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $337.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-23Southwest AirlinesWN3556 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-23Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $337.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-24Southwest AirlinesWN3556 / WN3004Axel-exclusive $292.502026-10-29T01:57:06Z
2026-12-10 → 2026-12-24Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004Axel-exclusive $337.502026-10-29T01:57:06Z

Route overview: Pittsburgh to Chicago (MDW) flight deals

2026-12-10 · one way · Axel-exclusive $135.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.

2026-12-10 · one way · Axel-exclusive $185.00

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

2026-12-10 → 2026-12-11 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2026-12-11 08:15:00 → PIT 2026-12-11 10:40:00; nonstop; 85 minutes. Local airport times.

2026-12-10 → 2026-12-11 · Axel-exclusive $305.00

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

2026-12-10 → 2026-12-12 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-12 18:55:00 → PIT 2026-12-12 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-10 → 2026-12-12 · Axel-exclusive $305.00

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

2026-12-10 → 2026-12-13 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-13 18:50:00 → PIT 2026-12-13 21:20:00; nonstop; 90 minutes. Local airport times.

2026-12-10 → 2026-12-13 · Axel-exclusive $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-13 18:50:00 → PIT 2026-12-13 21:20:00; nonstop; 90 minutes. Local airport times.

2026-12-10 → 2026-12-14 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-14 18:10:00 → PIT 2026-12-14 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-14 · Axel-exclusive $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-14 18:10:00 → PIT 2026-12-14 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-16 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-16 18:10:00 → PIT 2026-12-16 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-16 · Axel-exclusive $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-16 18:10:00 → PIT 2026-12-16 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-17 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-17 18:10:00 → PIT 2026-12-17 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-17 · Axel-exclusive $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-17 18:10:00 → PIT 2026-12-17 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-18 · Axel-exclusive $260.00

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-18 18:10:00 → PIT 2026-12-18 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-18 · Axel-exclusive $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-18 18:10:00 → PIT 2026-12-18 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-20 · Axel-exclusive $292.50

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-20 07:45:00 → PIT 2026-12-20 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-10 → 2026-12-20 · Axel-exclusive $337.50

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-12-20 07:45:00 → PIT 2026-12-20 10:05:00; nonstop; 80 minutes. Local airport times.

2026-12-10 → 2026-12-21 · Axel-exclusive $292.50

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-21 18:55:00 → PIT 2026-12-21 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-10 → 2026-12-21 · Axel-exclusive $337.50

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

2026-12-10 → 2026-12-22 · Axel-exclusive $292.50

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-22 18:10:00 → PIT 2026-12-22 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-22 · Axel-exclusive $337.50

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-22 18:10:00 → PIT 2026-12-22 20:45:00; nonstop; 95 minutes. Local airport times.

2026-12-10 → 2026-12-24 · Axel-exclusive $292.50

  • Southwest Airlines WN3556: PIT 2026-12-10 19:25:00 → MDW 2026-12-10 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2026-12-24 18:55:00 → PIT 2026-12-24 21:25:00; nonstop; 90 minutes. Local airport times.

2026-12-10 → 2026-12-24 · Axel-exclusive $337.50

  • Delta Air Lines DL5738 / DL4688: PIT 2026-12-10 10:31:00 → MDW 2026-12-10 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-12-10 10:31:00 → DTW 2026-12-10 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-12-10 12:44:00 → MDW 2026-12-10 13:01:00.
  • Southwest Airlines WN3004: MDW 2026-12-24 18:55:00 → PIT 2026-12-24 21:25:00; nonstop; 90 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Pittsburgh (PIT) to Chicago (MDW) · Dec 10, 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.