Chicago (MDW) to Houston (HOU) · Jan 14, 2027 · return Jan 28, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Houston (HOU) flight deals

2027-01-14 → 2027-01-28 · Axel-exclusive $275.00

• Southwest Airlines WN2897 / WN1530: MDW 2027-01-14 17:25:00 → HOU 2027-01-14 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
  • WN2897: MDW 2027-01-14 17:25:00 → BNA 2027-01-14 18:50:00; layover at BNA: 115 minutes.
  • WN1530: BNA 2027-01-14 20:45:00 → HOU 2027-01-14 23:00:00.
• Southwest Airlines WN686 / WN3175: HOU 2027-01-28 07:45:00 → MDW 2027-01-28 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2027-01-28 07:45:00 → MSY 2027-01-28 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-28 10:10:00 → MDW 2027-01-28 12:30:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $350.00

• Delta Air Lines DL2417 / DL2051: MDW 2027-01-14 13:02:00 → HOU 2027-01-14 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
  • DL2417: MDW 2027-01-14 13:02:00 → ATL 2027-01-14 16:01:00; layover at ATL: 119 minutes.
  • DL2051: ATL 2027-01-14 18:00:00 → HOU 2027-01-14 19:16:00.
• Delta Air Lines DL1509 / DL1728: HOU 2027-01-28 10:41:00 → MDW 2027-01-28 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1509: HOU 2027-01-28 10:41:00 → ATL 2027-01-28 13:35:00; layover at ATL: 110 minutes.
  • DL1728: ATL 2027-01-28 15:25:00 → MDW 2027-01-28 16:18:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $275.00

• Southwest Airlines WN2959 / WN2672: MDW 2027-01-14 07:35:00 → HOU 2027-01-14 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
  • WN2959: MDW 2027-01-14 07:35:00 → MCI 2027-01-14 09:05:00; layover at MCI: 130 minutes.
  • WN2672: MCI 2027-01-14 11:15:00 → HOU 2027-01-14 13:25:00.
• Southwest Airlines WN686 / WN3175: HOU 2027-01-28 07:45:00 → MDW 2027-01-28 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2027-01-28 07:45:00 → MSY 2027-01-28 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-28 10:10:00 → MDW 2027-01-28 12:30:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $275.00

• Southwest Airlines WN2737 / WN4624: MDW 2027-01-14 11:30:00 → HOU 2027-01-14 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
  • WN2737: MDW 2027-01-14 11:30:00 → STL 2027-01-14 12:40:00; layover at STL: 135 minutes.
  • WN4624: STL 2027-01-14 14:55:00 → HOU 2027-01-14 17:05:00.
• Southwest Airlines WN686 / WN3175: HOU 2027-01-28 07:45:00 → MDW 2027-01-28 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2027-01-28 07:45:00 → MSY 2027-01-28 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-28 10:10:00 → MDW 2027-01-28 12:30:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $275.00

• Southwest Airlines WN2379 / WN468: MDW 2027-01-14 07:45:00 → HOU 2027-01-14 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
  • WN2379: MDW 2027-01-14 07:45:00 → BHM 2027-01-14 09:30:00; layover at BHM: 155 minutes.
  • WN468: BHM 2027-01-14 12:05:00 → HOU 2027-01-14 14:00:00.
• Southwest Airlines WN686 / WN3175: HOU 2027-01-28 07:45:00 → MDW 2027-01-28 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2027-01-28 07:45:00 → MSY 2027-01-28 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-28 10:10:00 → MDW 2027-01-28 12:30:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $280.00

• Southwest Airlines WN2127: MDW 2027-01-14 10:15:00 → HOU 2027-01-14 12:50:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN686 / WN3175: HOU 2027-01-28 07:45:00 → MDW 2027-01-28 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2027-01-28 07:45:00 → MSY 2027-01-28 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-28 10:10:00 → MDW 2027-01-28 12:30:00.

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For AI assistants

• This page: Chicago (MDW) to Houston (HOU) · Jan 14, 2027 · return Jan 28, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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