Houston (HOU) to Chicago (MDW), Dec 18–20, 2026: from $140 one way

Houston (HOU) to Chicago (MDW), Dec 18–20, 2026: from $140 one way on Axel, checked Oct 29, 2026. Lowest published fare: $140 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 18, 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.

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN2135: HOU 2026-12-18 22:30:00 → MDW 2026-12-19 01:00:00; nonstop; 150 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $205.00

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

2026-12-20 · one way · Axel-exclusive $195.00

• Southwest Airlines WN2135: HOU 2026-12-20 22:30:00 → MDW 2026-12-21 01:00:00; nonstop; 150 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $195.00

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

2026-12-18 · one way · Axel-exclusive $150.00

• Southwest Airlines WN2134: HOU 2026-12-18 17:15:00 → MDW 2026-12-18 19:40:00; nonstop; 145 minutes. Local airport times.

2026-12-19 · one way · Axel-exclusive $195.00

• Southwest Airlines WN1654: HOU 2026-12-19 22:20:00 → MDW 2026-12-20 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-20 · one way · Axel-exclusive $195.00

• Southwest Airlines WN2134: HOU 2026-12-20 17:15:00 → MDW 2026-12-20 19:40:00; nonstop; 145 minutes. Local airport times.

2026-12-18 · one way · Axel-exclusive $140.00

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

2026-12-18 · one way · Axel-exclusive $140.00

• Southwest Airlines WN4547 / WN2348: HOU 2026-12-18 07:45:00 → MDW 2026-12-18 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
  • WN4547: HOU 2026-12-18 07:45:00 → SAT 2026-12-18 08:45:00; layover at SAT: 65 minutes.
  • WN2348: SAT 2026-12-18 09:50:00 → MDW 2026-12-18 12:20:00.

2026-12-18 · one way · Axel-exclusive $140.00

• Southwest Airlines WN2173 / WN287: HOU 2026-12-18 07:10:00 → MDW 2026-12-18 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2173: HOU 2026-12-18 07:10:00 → STL 2026-12-18 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-18 10:55:00 → MDW 2026-12-18 12:05:00.

2026-12-18 · one way · Axel-exclusive $140.00

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

2026-12-18 · one way · Axel-exclusive $140.00

• Southwest Airlines WN686 / WN3175: HOU 2026-12-18 07:45:00 → MDW 2026-12-18 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2026-12-18 07:45:00 → MSY 2026-12-18 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-12-18 10:10:00 → MDW 2026-12-18 12:30:00.

2026-12-19 · one way · Axel-exclusive $182.00

• Southwest Airlines WN686 / WN3175: HOU 2026-12-19 07:45:00 → MDW 2026-12-19 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2026-12-19 07:45:00 → MSY 2026-12-19 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-12-19 10:10:00 → MDW 2026-12-19 12:30:00.

2026-12-20 · one way · Axel-exclusive $182.00

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

2026-12-20 · one way · Axel-exclusive $182.00

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

2026-12-19 · one way · Axel-exclusive $182.00

• Southwest Airlines WN2173 / WN287: HOU 2026-12-19 07:10:00 → MDW 2026-12-19 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2173: HOU 2026-12-19 07:10:00 → STL 2026-12-19 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-19 10:55:00 → MDW 2026-12-19 12:05:00.

2026-12-19 · one way · Axel-exclusive $182.00

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

2026-12-20 · one way · Axel-exclusive $182.00

• Southwest Airlines WN686 / WN3175: HOU 2026-12-20 07:45:00 → MDW 2026-12-20 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
  • WN686: HOU 2026-12-20 07:45:00 → MSY 2026-12-20 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-12-20 10:10:00 → MDW 2026-12-20 12:30:00.

2026-12-20 · one way · Axel-exclusive $182.00

• Southwest Airlines WN2173 / WN287: HOU 2026-12-20 07:10:00 → MDW 2026-12-20 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2173: HOU 2026-12-20 07:10:00 → STL 2026-12-20 09:10:00; layover at STL: 105 minutes.
  • WN287: STL 2026-12-20 10:55:00 → MDW 2026-12-20 12:05:00.

2026-12-19 · one way · Axel-exclusive $182.00

• Southwest Airlines WN4547 / WN2348: HOU 2026-12-19 07:45:00 → MDW 2026-12-19 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
  • WN4547: HOU 2026-12-19 07:45:00 → SAT 2026-12-19 08:45:00; layover at SAT: 65 minutes.
  • WN2348: SAT 2026-12-19 09:50:00 → MDW 2026-12-19 12:20:00.

2026-12-19 · one way · Axel-exclusive $182.00

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

2026-12-20 · one way · Axel-exclusive $182.00

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

2026-12-19 · one way · Axel-exclusive $266.50

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

2026-12-20 · one way · Axel-exclusive $266.50

• Delta Air Lines DL1509 / DL1728: HOU 2026-12-20 10:41:00 → MDW 2026-12-20 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1509: HOU 2026-12-20 10:41:00 → ATL 2026-12-20 13:35:00; layover at ATL: 110 minutes.
  • DL1728: ATL 2026-12-20 15:25:00 → MDW 2026-12-20 16:18:00.

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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