Houston (HOU) to Chicago (MDW), Nov 7–14, 2026: from $283 round trip

Houston (HOU) to Chicago (MDW), Nov 7–14, 2026: from $283 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $283 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 7–14, 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.

2026-11-07 → 2026-11-14 · Axel-exclusive $290.00

• Southwest Airlines WN2133: HOU 2026-11-07 14:35:00 → MDW 2026-11-07 17:00:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $395.00

• Delta Air Lines DL1509 / DL1728: HOU 2026-11-07 10:41:00 → MDW 2026-11-07 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1509: HOU 2026-11-07 10:41:00 → ATL 2026-11-07 13:35:00; layover at ATL: 110 minutes.
  • DL1728: ATL 2026-11-07 15:25:00 → MDW 2026-11-07 16:18:00.
• Delta Air Lines DL2417 / DL2051: MDW 2026-11-14 13:02:00 → HOU 2026-11-14 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
  • DL2417: MDW 2026-11-14 13:02:00 → ATL 2026-11-14 16:01:00; layover at ATL: 119 minutes.
  • DL2051: ATL 2026-11-14 18:00:00 → HOU 2026-11-14 19:16:00.

2026-11-07 → 2026-11-14 · Axel-exclusive $290.00

• Southwest Airlines WN1654: HOU 2026-11-07 22:20:00 → MDW 2026-11-08 00:50:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $282.50

• Southwest Airlines WN2211 / WN1718: HOU 2026-11-07 14:55:00 → MDW 2026-11-07 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
  • WN2211: HOU 2026-11-07 14:55:00 → CMH 2026-11-07 18:20:00; layover at CMH: 70 minutes.
  • WN1718: CMH 2026-11-07 19:30:00 → MDW 2026-11-07 19:40:00.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $282.50

• Southwest Airlines WN2173 / WN287: HOU 2026-11-07 07:10:00 → MDW 2026-11-07 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2173: HOU 2026-11-07 07:10:00 → STL 2026-11-07 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-11-07 10:55:00 → MDW 2026-11-07 12:05:00.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $282.50

• Southwest Airlines WN4547 / WN2348: HOU 2026-11-07 07:45:00 → MDW 2026-11-07 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
  • WN4547: HOU 2026-11-07 07:45:00 → SAT 2026-11-07 08:45:00; layover at SAT: 65 minutes.
  • WN2348: SAT 2026-11-07 09:50:00 → MDW 2026-11-07 12:20:00.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $282.50

• Southwest Airlines WN4610 / WN3556: HOU 2026-11-07 14:45:00 → MDW 2026-11-07 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
  • WN4610: HOU 2026-11-07 14:45:00 → PIT 2026-11-07 18:25:00; layover at PIT: 75 minutes.
  • WN3556: PIT 2026-11-07 19:40:00 → MDW 2026-11-07 20:10:00.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

2026-11-07 → 2026-11-14 · Axel-exclusive $282.50

• Southwest Airlines WN686 / WN3175: HOU 2026-11-07 07:45:00 → MDW 2026-11-07 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2026-11-07 07:45:00 → MSY 2026-11-07 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-11-07 10:10:00 → MDW 2026-11-07 12:30:00.
• Southwest Airlines WN2127: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; nonstop; 155 minutes. Local airport times.

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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