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Houston → Chicago

Dec 27, 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 27, 2026 · One waySouthwest AirlinesNonstop$195.00 Dec 27, 2026 · One wayDelta Air LinesUp to 1 stop each way$266.50 Dec 27, 2026 – Dec 28, 2026 · 1 nightSouthwest AirlinesUp to 1 stop each way$367.25 Dec 27, 2026 – Dec 28, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$513.50 Dec 27, 2026 – Dec 29, 2026 · 2 nightsSouthwest AirlinesNonstop$377.00 Dec 27, 2026 – Dec 29, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$513.50 Dec 27, 2026 – Dec 30, 2026 · 3 nightsSouthwest AirlinesNonstop$377.00 Dec 27, 2026 – Dec 30, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$513.50 Dec 27, 2026 – Dec 31, 2026 · 4 nightsSouthwest AirlinesUp to 1 stop each way$367.25 Dec 27, 2026 – Dec 31, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$513.50 Dec 27, 2026 – Jan 1, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$357.63 Dec 27, 2026 – Jan 1, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$499.68 Dec 27, 2026 – Jan 2, 2027 · 6 nightsSouthwest AirlinesNonstop$366.85 Dec 27, 2026 – Jan 2, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$499.68 Dec 27, 2026 – Jan 3, 2027 · 7 nightsSouthwest AirlinesNonstop$366.85 Dec 27, 2026 – Jan 3, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$499.68 Dec 27, 2026 – Jan 4, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$319.13 Dec 27, 2026 – Jan 4, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 5, 2027 · 9 nightsSouthwest AirlinesNonstop$326.25 Dec 27, 2026 – Jan 5, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 6, 2027 · 10 nightsSouthwest AirlinesNonstop$326.25 Dec 27, 2026 – Jan 6, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 7, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$319.13 Dec 27, 2026 – Jan 7, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 8, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$319.13 Dec 27, 2026 – Jan 8, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 9, 2027 · 13 nightsSouthwest AirlinesNonstop$326.25 Dec 27, 2026 – Jan 9, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$444.38 Dec 27, 2026 – Jan 10, 2027 · 14 nightsSouthwest AirlinesNonstop$326.25 Dec 27, 2026 – Jan 10, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$444.38

Flights for your trip

  1. Sun, Dec 27 · One way

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Sun, Dec 27 · One way

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

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Sun, Dec 27 – Mon, Dec 28

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    7:45 amMDW
    6h 15m
    BHM · 2h 35m
    2:00 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Sun, Dec 27 – Mon, Dec 28

    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

    Availability is checked when you select these flights.

  5. Sun, Dec 27 – Tue, Dec 29

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Sun, Dec 27 – 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

    Availability is checked when you select these flights.

  7. Sun, Dec 27 – Wed, Dec 30

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Sun, Dec 27 – Wed, Dec 30

    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

    Availability is checked when you select these flights.

  9. Sun, Dec 27 – Thu, Dec 31

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    11:30 amMDW
    5h 35m
    STL · 2h 15m
    5:05 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Sun, Dec 27 – Thu, Dec 31

    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

    Availability is checked when you select these flights.

  11. Sun, Dec 27 – Sat, Jan 2

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Sun, Dec 27 – Sat, Jan 2

    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

    Availability is checked when you select these flights.

  13. Sun, Dec 27 – Sun, Jan 3

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    4:30 pmMDW
    2h 40m
    Nonstop
    7:10 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  14. Sun, Dec 27 – Sun, Jan 3

    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

    Availability is checked when you select these flights.

  15. Sun, Dec 27 – Mon, Jan 4

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    7:45 amMDW
    6h 15m
    BHM · 2h 35m
    2:00 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Sun, Dec 27 – Mon, Jan 4

    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

    Availability is checked when you select these flights.

  17. Sun, Dec 27 – Wed, Jan 6

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    10:15 amMDW
    2h 35m
    Nonstop
    12:50 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Sun, Dec 27 – Wed, Jan 6

    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

    Availability is checked when you select these flights.

  19. Sun, Dec 27 – Thu, Jan 7

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    11:30 amMDW
    5h 35m
    STL · 2h 15m
    5:05 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Sun, Dec 27 – Thu, Jan 7

    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

    Availability is checked when you select these flights.

  21. Sun, Dec 27 – Fri, Jan 8

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    5:25 pmMDW
    5h 35m
    BNA · 1h 55m
    11:00 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Sun, Dec 27 – Fri, Jan 8

    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

    Availability is checked when you select these flights.

  23. Sun, Dec 27 – Sun, Jan 10

    Southwest Airlines
    5:15 pmHOU
    2h 25m
    Nonstop
    7:40 pmMDW
    Southwest Airlines
    4:30 pmMDW
    2h 40m
    Nonstop
    7:10 pmHOU

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  24. Sun, Dec 27 – Sun, Jan 10

    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

    Availability is checked when you select these flights.

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Make this trip yours

HOU ⇄ 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 26, 2026 · Return optionsDec 28, 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)
2026-12-27 · one waySouthwest AirlinesWN2134Axel-exclusive $195.002026-10-29T01:04:53Z
2026-12-27 · one wayDelta Air LinesDL1509 + DL1728Axel-exclusive $266.502026-10-29T01:04:53Z
2026-12-27 → 2026-12-28Southwest AirlinesWN2134 / WN2379 + WN468Axel-exclusive $367.252026-10-29T01:04:53Z
2026-12-27 → 2026-12-28Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $513.502026-10-29T01:04:53Z
2026-12-27 → 2026-12-29Southwest AirlinesWN2134 / WN4395Axel-exclusive $377.002026-10-29T01:04:53Z
2026-12-27 → 2026-12-29Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $513.502026-10-29T01:04:53Z
2026-12-27 → 2026-12-30Southwest AirlinesWN2134 / WN2127Axel-exclusive $377.002026-10-29T01:04:53Z
2026-12-27 → 2026-12-30Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $513.502026-10-29T01:04:53Z
2026-12-27 → 2026-12-31Southwest AirlinesWN2134 / WN2737 + WN4624Axel-exclusive $367.252026-10-29T01:04:53Z
2026-12-27 → 2026-12-31Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $513.502026-10-29T01:04:53Z
2026-12-27 → 2027-01-01Southwest AirlinesWN2134 / WN2897 + WN1530Axel-exclusive $357.632026-10-29T01:04:53Z
2026-12-27 → 2027-01-01Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $499.682026-10-29T01:04:53Z
2026-12-27 → 2027-01-02Southwest AirlinesWN2134 / WN2127Axel-exclusive $366.852026-10-29T01:04:53Z
2026-12-27 → 2027-01-02Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $499.682026-10-29T01:04:53Z
2026-12-27 → 2027-01-03Southwest AirlinesWN2134 / WN4482Axel-exclusive $366.852026-10-29T01:04:53Z
2026-12-27 → 2027-01-03Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $499.682026-10-29T01:04:53Z
2026-12-27 → 2027-01-04Southwest AirlinesWN2134 / WN2379 + WN468Axel-exclusive $319.132026-10-29T01:04:53Z
2026-12-27 → 2027-01-04Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-05Southwest AirlinesWN2134 / WN4395Axel-exclusive $326.252026-10-29T01:04:53Z
2026-12-27 → 2027-01-05Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-06Southwest AirlinesWN2134 / WN2127Axel-exclusive $326.252026-10-29T01:04:53Z
2026-12-27 → 2027-01-06Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-07Southwest AirlinesWN2134 / WN2737 + WN4624Axel-exclusive $319.132026-10-29T01:04:53Z
2026-12-27 → 2027-01-07Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-08Southwest AirlinesWN2134 / WN2897 + WN1530Axel-exclusive $319.132026-10-29T01:04:53Z
2026-12-27 → 2027-01-08Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-09Southwest AirlinesWN2134 / WN2127Axel-exclusive $326.252026-10-29T01:04:53Z
2026-12-27 → 2027-01-09Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z
2026-12-27 → 2027-01-10Southwest AirlinesWN2134 / WN4482Axel-exclusive $326.252026-10-29T01:04:53Z
2026-12-27 → 2027-01-10Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051Axel-exclusive $444.382026-10-29T01:04:53Z

2026-12-27 · one way · Axel-exclusive $195.00

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $266.50

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

2026-12-27 → 2026-12-28 · Axel-exclusive $367.25

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2379 / WN468: MDW 2026-12-28 07:45:00 → HOU 2026-12-28 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
    • WN2379: MDW 2026-12-28 07:45:00 → BHM 2026-12-28 09:30:00; layover at BHM: 155 minutes.
    • WN468: BHM 2026-12-28 12:05:00 → HOU 2026-12-28 14:00:00.

2026-12-27 → 2026-12-28 · Axel-exclusive $513.50

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-28 13:02:00 → HOU 2026-12-28 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-28 13:02:00 → ATL 2026-12-28 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-28 18:00:00 → HOU 2026-12-28 19:16:00.

2026-12-27 → 2026-12-29 · Axel-exclusive $377.00

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; 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.

2026-12-27 → 2026-12-29 · Axel-exclusive $513.50

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

2026-12-27 → 2026-12-30 · Axel-exclusive $377.00

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2127: MDW 2026-12-30 10:15:00 → HOU 2026-12-30 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $513.50

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-30 13:02:00 → HOU 2026-12-30 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-30 13:02:00 → ATL 2026-12-30 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-30 18:00:00 → HOU 2026-12-30 19:16:00.

2026-12-27 → 2026-12-31 · Axel-exclusive $367.25

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2737 / WN4624: MDW 2026-12-31 11:30:00 → HOU 2026-12-31 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2026-12-31 14:55:00 → HOU 2026-12-31 17:05:00.

2026-12-27 → 2026-12-31 · Axel-exclusive $513.50

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-31 13:02:00 → HOU 2026-12-31 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-31 13:02:00 → ATL 2026-12-31 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-31 18:00:00 → HOU 2026-12-31 19:16:00.

2026-12-27 → 2027-01-02 · Axel-exclusive $366.85

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2127: MDW 2027-01-02 10:15:00 → HOU 2027-01-02 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-27 → 2027-01-02 · Axel-exclusive $499.68

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-02 13:02:00 → HOU 2027-01-02 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-02 13:02:00 → ATL 2027-01-02 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-02 18:00:00 → HOU 2027-01-02 19:16:00.

2026-12-27 → 2027-01-03 · Axel-exclusive $366.85

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4482: MDW 2027-01-03 16:30:00 → HOU 2027-01-03 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-27 → 2027-01-03 · Axel-exclusive $499.68

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-03 13:02:00 → HOU 2027-01-03 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-03 13:02:00 → ATL 2027-01-03 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-03 18:00:00 → HOU 2027-01-03 19:16:00.

2026-12-27 → 2027-01-04 · Axel-exclusive $319.13

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2379 / WN468: MDW 2027-01-04 07:45:00 → HOU 2027-01-04 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
    • WN2379: MDW 2027-01-04 07:45:00 → BHM 2027-01-04 09:30:00; layover at BHM: 155 minutes.
    • WN468: BHM 2027-01-04 12:05:00 → HOU 2027-01-04 14:00:00.

2026-12-27 → 2027-01-04 · Axel-exclusive $444.38

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-04 13:02:00 → HOU 2027-01-04 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-04 13:02:00 → ATL 2027-01-04 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-04 18:00:00 → HOU 2027-01-04 19:16:00.

2026-12-27 → 2027-01-06 · Axel-exclusive $326.25

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2127: MDW 2027-01-06 10:15:00 → HOU 2027-01-06 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $444.38

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-06 13:02:00 → HOU 2027-01-06 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-06 13:02:00 → ATL 2027-01-06 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-06 18:00:00 → HOU 2027-01-06 19:16:00.

2026-12-27 → 2027-01-07 · Axel-exclusive $319.13

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2737 / WN4624: MDW 2027-01-07 11:30:00 → HOU 2027-01-07 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2027-01-07 11:30:00 → STL 2027-01-07 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2027-01-07 14:55:00 → HOU 2027-01-07 17:05:00.

2026-12-27 → 2027-01-07 · Axel-exclusive $444.38

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-07 13:02:00 → HOU 2027-01-07 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-07 13:02:00 → ATL 2027-01-07 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-07 18:00:00 → HOU 2027-01-07 19:16:00.

2026-12-27 → 2027-01-08 · Axel-exclusive $319.13

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1530: MDW 2027-01-08 17:25:00 → HOU 2027-01-08 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2027-01-08 17:25:00 → BNA 2027-01-08 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2027-01-08 20:45:00 → HOU 2027-01-08 23:00:00.

2026-12-27 → 2027-01-08 · Axel-exclusive $444.38

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-08 13:02:00 → HOU 2027-01-08 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-08 13:02:00 → ATL 2027-01-08 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-08 18:00:00 → HOU 2027-01-08 19:16:00.

2026-12-27 → 2027-01-10 · Axel-exclusive $326.25

  • Southwest Airlines WN2134: HOU 2026-12-27 17:15:00 → MDW 2026-12-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4482: MDW 2027-01-10 16:30:00 → HOU 2027-01-10 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $444.38

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-27 10:41:00 → MDW 2026-12-27 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-27 10:41:00 → ATL 2026-12-27 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-27 15:25:00 → MDW 2026-12-27 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2027-01-10 13:02:00 → HOU 2027-01-10 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2027-01-10 13:02:00 → ATL 2027-01-10 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2027-01-10 18:00:00 → HOU 2027-01-10 19:16:00.

Explore this route

For AI assistants

  • This page: Houston (HOU) to Chicago (MDW) · Dec 27, 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. 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.