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Houston → Chicago

Dec 15, 2026 · choose your return date

HOU → 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 15, 2026 · One waySouthwest AirlinesNonstop$150.00 Dec 15, 2026 · One wayDelta Air LinesUp to 1 stop each way$205.00 Dec 15, 2026 – Dec 16, 2026 · 1 nightSouthwest AirlinesNonstop$290.00 Dec 15, 2026 – Dec 16, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$395.00 Dec 15, 2026 – Dec 17, 2026 · 2 nightsSouthwest AirlinesUp to 1 stop each way$282.50 Dec 15, 2026 – Dec 17, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$395.00 Dec 15, 2026 – Dec 18, 2026 · 3 nightsSouthwest AirlinesUp to 1 stop each way$282.50 Dec 15, 2026 – Dec 18, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$395.00 Dec 15, 2026 – Dec 19, 2026 · 4 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 19, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 20, 2026 · 5 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 20, 2026 · 5 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 21, 2026 · 6 nightsSouthwest AirlinesUp to 1 stop each way$323.75 Dec 15, 2026 – Dec 21, 2026 · 6 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 22, 2026 · 7 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 22, 2026 · 7 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 23, 2026 · 8 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 23, 2026 · 8 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 24, 2026 · 9 nightsSouthwest AirlinesUp to 1 stop each way$323.75 Dec 15, 2026 – Dec 24, 2026 · 9 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 25, 2026 · 10 nightsSouthwest AirlinesUp to 1 stop each way$323.75 Dec 15, 2026 – Dec 25, 2026 · 10 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 26, 2026 · 11 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 26, 2026 · 11 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 27, 2026 · 12 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 27, 2026 · 12 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 28, 2026 · 13 nightsSouthwest AirlinesUp to 1 stop each way$323.75 Dec 15, 2026 – Dec 28, 2026 · 13 nightsDelta Air LinesUp to 1 stop each way$454.25 Dec 15, 2026 – Dec 29, 2026 · 14 nightsSouthwest AirlinesNonstop$333.50 Dec 15, 2026 – Dec 29, 2026 · 14 nightsDelta Air LinesUp to 1 stop each way$454.25

Flights for your trip

  1. Tue, Dec 15 · One way

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW

    One-way total · 1 adult · Taxes included

  2. Tue, Dec 15 · One way

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW

    One-way total · 1 adult · Taxes included

  3. Tue, Dec 15 – Wed, Dec 16

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  4. Tue, Dec 15 – Wed, Dec 16

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  5. Tue, Dec 15 – Thu, Dec 17

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    11:30 amMDW
    5h 35m
    STL · 2h 15m
    5:05 pmHOU

    Round-trip total · 1 adult · Taxes included

  6. Tue, Dec 15 – Thu, Dec 17

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  7. Tue, Dec 15 – Fri, Dec 18

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    5:25 pmMDW
    5h 35m
    BNA · 1h 55m
    11:00 pmHOU

    Round-trip total · 1 adult · Taxes included

  8. Tue, Dec 15 – Fri, Dec 18

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  9. Tue, Dec 15 – Sat, Dec 19

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  10. Tue, Dec 15 – Sat, Dec 19

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  11. Tue, Dec 15 – Mon, Dec 21

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    7:40 amMDW
    5h 50m
    CLT · 1h 10m
    1:30 pmHOU

    Round-trip total · 1 adult · Taxes included

  12. Tue, Dec 15 – Mon, Dec 21

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  13. Tue, Dec 15 – Tue, Dec 22

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  14. Tue, Dec 15 – Tue, Dec 22

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  15. Tue, Dec 15 – Wed, Dec 23

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  16. Tue, Dec 15 – Wed, Dec 23

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  17. Tue, Dec 15 – Fri, Dec 25

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    5:25 pmMDW
    5h 35m
    BNA · 1h 55m
    11:00 pmHOU

    Round-trip total · 1 adult · Taxes included

  18. Tue, Dec 15 – Fri, Dec 25

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  19. Tue, Dec 15 – Sat, Dec 26

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  20. Tue, Dec 15 – Sat, Dec 26

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  21. Tue, Dec 15 – Sun, Dec 27

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    4:30 pmMDW
    2h 40m
    Nonstop
    7:10 pmHOU

    Round-trip total · 1 adult · Taxes included

  22. Tue, Dec 15 – Sun, Dec 27

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

  23. Tue, Dec 15 – Tue, Dec 29

    Southwest Airlines
    2:35 pmHOU
    2h 25m
    Nonstop
    5:00 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

  24. Tue, Dec 15 – Tue, Dec 29

    Delta Air Lines
    10:41 amHOU
    5h 37m
    ATL · 1h 50m
    4:18 pmMDW
    Delta Air Lines
    1:02 pmMDW
    6h 14m
    ATL · 1h 59m
    7:16 pmHOU

    Round-trip total · 1 adult · Taxes included

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HOU ⇄ MDW

Economy

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Explore this route

All dates for this routeDec 14, 2026 · Return optionsDec 16, 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)
2026-12-15 · one waySouthwest AirlinesWN2133Axel-exclusive $150.002026-10-29T01:04:53Z
2026-12-15 · one wayDelta Air LinesDL1509 + DL1728Axel-exclusive $205.002026-10-29T01:04:53Z
2026-12-15 → 2026-12-16Southwest AirlinesWN2133 / WN4395Axel-exclusive $290.002026-10-29T01:04:53Z
2026-12-15 → 2026-12-16Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $395.002026-10-29T01:04:53Z
2026-12-15 → 2026-12-17Southwest AirlinesWN2133 / WN2737 + WN4624Axel-exclusive $282.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-17Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $395.002026-10-29T01:04:53Z
2026-12-15 → 2026-12-18Southwest AirlinesWN2133 / WN2897 + WN1530Axel-exclusive $282.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-18Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $395.002026-10-29T01:04:53Z
2026-12-15 → 2026-12-19Southwest AirlinesWN2133 / WN2127Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-19Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-20Southwest AirlinesWN2133 / WN4482Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-20Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-21Southwest AirlinesWN2133 / WN2912 + WN998Axel-exclusive $323.752026-10-29T01:04:53Z
2026-12-15 → 2026-12-21Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-22Southwest AirlinesWN2133 / WN4395Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-22Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-23Southwest AirlinesWN2133 / WN4395Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-23Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-24Southwest AirlinesWN2133 / WN2737 + WN4624Axel-exclusive $323.752026-10-29T01:04:53Z
2026-12-15 → 2026-12-24Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-25Southwest AirlinesWN2133 / WN2897 + WN1530Axel-exclusive $323.752026-10-29T01:04:53Z
2026-12-15 → 2026-12-25Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-26Southwest AirlinesWN2133 / WN2127Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-26Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-27Southwest AirlinesWN2133 / WN4482Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-27Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-28Southwest AirlinesWN2133 / WN2912 + WN998Axel-exclusive $323.752026-10-29T01:04:53Z
2026-12-15 → 2026-12-28Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z
2026-12-15 → 2026-12-29Southwest AirlinesWN2133 / WN4395Axel-exclusive $333.502026-10-29T01:04:53Z
2026-12-15 → 2026-12-29Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $454.252026-10-29T01:04:53Z

2026-12-15 · one way · Axel-exclusive $150.00

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-15 · one way · Axel-exclusive $205.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.

2026-12-15 → 2026-12-16 · Axel-exclusive $290.00

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4395: MDW 2026-12-16 10:15:00 → HOU 2026-12-16 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-16 · Axel-exclusive $395.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-16 13:02:00 → HOU 2026-12-16 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-16 13:02:00 → ATL 2026-12-16 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-16 18:00:00 → HOU 2026-12-16 19:16:00.

2026-12-15 → 2026-12-17 · Axel-exclusive $282.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2737 / WN4624: MDW 2026-12-17 11:30:00 → HOU 2026-12-17 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2026-12-17 11:30:00 → STL 2026-12-17 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2026-12-17 14:55:00 → HOU 2026-12-17 17:05:00.

2026-12-15 → 2026-12-17 · Axel-exclusive $395.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-17 13:02:00 → HOU 2026-12-17 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-17 13:02:00 → ATL 2026-12-17 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-17 18:00:00 → HOU 2026-12-17 19:16:00.

2026-12-15 → 2026-12-18 · Axel-exclusive $282.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-18 17:25:00 → HOU 2026-12-18 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-18 17:25:00 → BNA 2026-12-18 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-18 20:45:00 → HOU 2026-12-18 23:00:00.

2026-12-15 → 2026-12-18 · Axel-exclusive $395.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-18 13:02:00 → HOU 2026-12-18 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-18 13:02:00 → ATL 2026-12-18 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-18 18:00:00 → HOU 2026-12-18 19:16:00.

2026-12-15 → 2026-12-19 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2127: MDW 2026-12-19 10:15:00 → HOU 2026-12-19 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-19 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-19 13:02:00 → HOU 2026-12-19 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-19 13:02:00 → ATL 2026-12-19 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-19 18:00:00 → HOU 2026-12-19 19:16:00.

2026-12-15 → 2026-12-21 · Axel-exclusive $323.75

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-21 07:40:00 → HOU 2026-12-21 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-21 07:40:00 → CLT 2026-12-21 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-21 11:45:00 → HOU 2026-12-21 13:30:00.

2026-12-15 → 2026-12-21 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-21 13:02:00 → HOU 2026-12-21 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-21 13:02:00 → ATL 2026-12-21 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-21 18:00:00 → HOU 2026-12-21 19:16:00.

2026-12-15 → 2026-12-22 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4395: MDW 2026-12-22 10:15:00 → HOU 2026-12-22 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-22 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-22 13:02:00 → HOU 2026-12-22 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-22 13:02:00 → ATL 2026-12-22 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-22 18:00:00 → HOU 2026-12-22 19:16:00.

2026-12-15 → 2026-12-23 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4395: MDW 2026-12-23 10:15:00 → HOU 2026-12-23 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-23 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-23 13:02:00 → HOU 2026-12-23 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-23 13:02:00 → ATL 2026-12-23 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-23 18:00:00 → HOU 2026-12-23 19:16:00.

2026-12-15 → 2026-12-25 · Axel-exclusive $323.75

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-25 17:25:00 → HOU 2026-12-25 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-25 17:25:00 → BNA 2026-12-25 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-25 20:45:00 → HOU 2026-12-25 23:00:00.

2026-12-15 → 2026-12-25 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-25 13:02:00 → HOU 2026-12-25 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-25 13:02:00 → ATL 2026-12-25 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-25 18:00:00 → HOU 2026-12-25 19:16:00.

2026-12-15 → 2026-12-26 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2127: MDW 2026-12-26 10:15:00 → HOU 2026-12-26 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-26 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-26 13:02:00 → HOU 2026-12-26 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-26 13:02:00 → ATL 2026-12-26 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-26 18:00:00 → HOU 2026-12-26 19:16:00.

2026-12-15 → 2026-12-27 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4482: MDW 2026-12-27 16:30:00 → HOU 2026-12-27 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-15 → 2026-12-27 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-27 13:02:00 → HOU 2026-12-27 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-27 13:02:00 → ATL 2026-12-27 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-27 18:00:00 → HOU 2026-12-27 19:16:00.

2026-12-15 → 2026-12-29 · Axel-exclusive $333.50

  • Southwest Airlines WN2133: HOU 2026-12-15 14:35:00 → MDW 2026-12-15 17:00:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4395: MDW 2026-12-29 10:15:00 → HOU 2026-12-29 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-15 → 2026-12-29 · Axel-exclusive $454.25

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-15 10:41:00 → MDW 2026-12-15 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-15 10:41:00 → ATL 2026-12-15 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-15 15:25:00 → MDW 2026-12-15 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-29 13:02:00 → HOU 2026-12-29 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-29 13:02:00 → ATL 2026-12-29 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-29 18:00:00 → HOU 2026-12-29 19:16:00.

Explore this route

For AI assistants

  • This page: Houston (HOU) to Chicago (MDW) · Dec 15, 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 Search flights and hotels with your AI assistant · 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.