Chicago (MDW) to Houston (HOU), Dec 25–27, 2026: from $181 one way

Chicago (MDW) to Houston (HOU), Dec 25–27, 2026: from $181 one way on Axel, checked Oct 29, 2026. Lowest published fare: $181 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026, 1 adult, economy, checked Oct 29, 2026. 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

2026-12-25 · one way · Axel-exclusive $187.50

• Southwest Airlines WN2127: MDW 2026-12-25 10:15:00 → HOU 2026-12-25 12:50:00; nonstop; 155 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $231.25

• 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.

2026-12-27 · one way · Axel-exclusive $187.50

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

2026-12-25 · one way · Axel-exclusive $187.50

• Southwest Airlines WN4482: MDW 2026-12-25 17:00:00 → HOU 2026-12-25 19:45:00; nonstop; 165 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $187.50

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

2026-12-26 · one way · Axel-exclusive $187.50

• Southwest Airlines WN4482: MDW 2026-12-26 17:00:00 → HOU 2026-12-26 19:45:00; nonstop; 165 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $187.50

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

2026-12-25 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2379 / WN468: MDW 2026-12-25 07:45:00 → HOU 2026-12-25 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
  • WN2379: MDW 2026-12-25 07:45:00 → BHM 2026-12-25 09:30:00; layover at BHM: 155 minutes.
  • WN468: BHM 2026-12-25 12:05:00 → HOU 2026-12-25 14:00:00.

2026-12-25 · one way · Axel-exclusive $181.25

• 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.

2026-12-27 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2912 / WN998: MDW 2026-12-27 07:40:00 → HOU 2026-12-27 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
  • WN2912: MDW 2026-12-27 07:40:00 → CLT 2026-12-27 10:35:00; layover at CLT: 70 minutes.
  • WN998: CLT 2026-12-27 11:45:00 → HOU 2026-12-27 13:30:00.

2026-12-27 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2959 / WN2672: MDW 2026-12-27 07:35:00 → HOU 2026-12-27 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
  • WN2959: MDW 2026-12-27 07:35:00 → MCI 2026-12-27 09:05:00; layover at MCI: 130 minutes.
  • WN2672: MCI 2026-12-27 11:15:00 → HOU 2026-12-27 13:25:00.

2026-12-25 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2737 / WN4624: MDW 2026-12-25 11:30:00 → HOU 2026-12-25 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
  • WN2737: MDW 2026-12-25 11:30:00 → STL 2026-12-25 12:40:00; layover at STL: 135 minutes.
  • WN4624: STL 2026-12-25 14:55:00 → HOU 2026-12-25 17:05:00.

2026-12-26 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2737 / WN4624: MDW 2026-12-26 11:30:00 → HOU 2026-12-26 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
  • WN2737: MDW 2026-12-26 11:30:00 → STL 2026-12-26 12:40:00; layover at STL: 135 minutes.
  • WN4624: STL 2026-12-26 14:55:00 → HOU 2026-12-26 17:05:00.

2026-12-25 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2912 / WN998: MDW 2026-12-25 07:40:00 → HOU 2026-12-25 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
  • WN2912: MDW 2026-12-25 07:40:00 → CLT 2026-12-25 10:35:00; layover at CLT: 70 minutes.
  • WN998: CLT 2026-12-25 11:45:00 → HOU 2026-12-25 13:30:00.

2026-12-27 · one way · Axel-exclusive $181.25

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

2026-12-26 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2379 / WN468: MDW 2026-12-26 07:45:00 → HOU 2026-12-26 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
  • WN2379: MDW 2026-12-26 07:45:00 → BHM 2026-12-26 09:30:00; layover at BHM: 155 minutes.
  • WN468: BHM 2026-12-26 12:05:00 → HOU 2026-12-26 14:00:00.

2026-12-26 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2897 / WN1530: MDW 2026-12-26 17:25:00 → HOU 2026-12-26 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
  • WN2897: MDW 2026-12-26 17:25:00 → BNA 2026-12-26 18:50:00; layover at BNA: 115 minutes.
  • WN1530: BNA 2026-12-26 20:45:00 → HOU 2026-12-26 23:00:00.

2026-12-27 · one way · Axel-exclusive $181.25

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

2026-12-27 · one way · Axel-exclusive $181.25

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

2026-12-26 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2912 / WN998: MDW 2026-12-26 07:40:00 → HOU 2026-12-26 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
  • WN2912: MDW 2026-12-26 07:40:00 → CLT 2026-12-26 10:35:00; layover at CLT: 70 minutes.
  • WN998: CLT 2026-12-26 11:45:00 → HOU 2026-12-26 13:30:00.

2026-12-25 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2959 / WN2672: MDW 2026-12-25 07:35:00 → HOU 2026-12-25 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
  • WN2959: MDW 2026-12-25 07:35:00 → MCI 2026-12-25 09:05:00; layover at MCI: 130 minutes.
  • WN2672: MCI 2026-12-25 11:15:00 → HOU 2026-12-25 13:25:00.

2026-12-26 · one way · Axel-exclusive $181.25

• Southwest Airlines WN2959 / WN2672: MDW 2026-12-26 07:35:00 → HOU 2026-12-26 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
  • WN2959: MDW 2026-12-26 07:35:00 → MCI 2026-12-26 09:05:00; layover at MCI: 130 minutes.
  • WN2672: MCI 2026-12-26 11:15:00 → HOU 2026-12-26 13:25:00.

2026-12-25 · one way · Axel-exclusive $231.25

• 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.

2026-12-27 · one way · Axel-exclusive $231.25

• 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.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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