San Antonio (SAT) to Chicago (MDW), Dec 4–6, 2026: from $155 one way

San Antonio (SAT) to Chicago (MDW), Dec 4–6, 2026: from $155 one way on Axel, checked Oct 29, 2026. Lowest published fare: $155 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 4, 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: San Antonio to Chicago (MDW) flight deals

2026-12-05 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2925: SAT 2026-12-05 15:15:00 → MDW 2026-12-05 17:50:00; nonstop; 155 minutes. Local airport times.

2026-12-05 · one way · Axel-exclusive $190.00

• Delta Air Lines DL2497 / DL4688: SAT 2026-12-05 05:25:00 → MDW 2026-12-05 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-12-05 05:25:00 → DTW 2026-12-05 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-12-05 12:44:00 → MDW 2026-12-05 13:01:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2348: SAT 2026-12-06 06:25:00 → MDW 2026-12-06 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-04 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3791: SAT 2026-12-04 14:50:00 → MDW 2026-12-04 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-05 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2348: SAT 2026-12-05 09:50:00 → MDW 2026-12-05 12:20:00; nonstop; 150 minutes. Local airport times.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-04 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2348: SAT 2026-12-04 09:50:00 → MDW 2026-12-04 12:20:00; nonstop; 150 minutes. Local airport times.

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN3801 / WN4175: SAT 2026-12-05 15:20:00 → MDW 2026-12-05 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2026-12-05 15:20:00 → STL 2026-12-05 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2026-12-05 18:55:00 → MDW 2026-12-05 20:00:00.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2991 / WN1005: SAT 2026-12-06 07:10:00 → MDW 2026-12-06 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2026-12-06 07:10:00 → BNA 2026-12-06 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2026-12-06 11:25:00 → MDW 2026-12-06 12:55:00.

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4494 / WN2134: SAT 2026-12-05 13:00:00 → MDW 2026-12-05 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2026-12-05 13:00:00 → HOU 2026-12-05 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2026-12-05 17:15:00 → MDW 2026-12-05 19:40:00.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN1506 / WN1433: SAT 2026-12-04 14:35:00 → MDW 2026-12-04 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
  • WN1506: SAT 2026-12-04 14:35:00 → DAL 2026-12-04 15:40:00; layover at DAL: 190 minutes.
  • WN1433: DAL 2026-12-04 18:50:00 → MDW 2026-12-04 21:00:00.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2991 / WN1005: SAT 2026-12-04 07:10:00 → MDW 2026-12-04 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2026-12-04 07:10:00 → BNA 2026-12-04 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2026-12-04 11:25:00 → MDW 2026-12-04 12:55:00.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4494 / WN2134: SAT 2026-12-06 13:00:00 → MDW 2026-12-06 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2026-12-06 13:00:00 → HOU 2026-12-06 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2026-12-06 17:15:00 → MDW 2026-12-06 19:40:00.

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN1506 / WN1433: SAT 2026-12-05 14:35:00 → MDW 2026-12-05 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
  • WN1506: SAT 2026-12-05 14:35:00 → DAL 2026-12-05 15:40:00; layover at DAL: 190 minutes.
  • WN1433: DAL 2026-12-05 18:50:00 → MDW 2026-12-05 21:00:00.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN3801 / WN4175: SAT 2026-12-06 15:20:00 → MDW 2026-12-06 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2026-12-06 15:20:00 → STL 2026-12-06 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2026-12-06 18:55:00 → MDW 2026-12-06 20:00:00.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN3801 / WN4175: SAT 2026-12-04 15:20:00 → MDW 2026-12-04 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2026-12-04 15:20:00 → STL 2026-12-04 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2026-12-04 18:55:00 → MDW 2026-12-04 20:00:00.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4494 / WN2134: SAT 2026-12-04 13:00:00 → MDW 2026-12-04 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2026-12-04 13:00:00 → HOU 2026-12-04 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2026-12-04 17:15:00 → MDW 2026-12-04 19:40:00.

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2991 / WN1005: SAT 2026-12-05 07:10:00 → MDW 2026-12-05 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2026-12-05 07:10:00 → BNA 2026-12-05 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2026-12-05 11:25:00 → MDW 2026-12-05 12:55:00.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN1506 / WN1433: SAT 2026-12-06 14:35:00 → MDW 2026-12-06 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
  • WN1506: SAT 2026-12-06 14:35:00 → DAL 2026-12-06 15:40:00; layover at DAL: 190 minutes.
  • WN1433: DAL 2026-12-06 18:50:00 → MDW 2026-12-06 21:00:00.

2026-12-04 · one way · Axel-exclusive $190.00

• Delta Air Lines DL2497 / DL4688: SAT 2026-12-04 05:25:00 → MDW 2026-12-04 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-12-04 05:25:00 → DTW 2026-12-04 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-12-04 12:44:00 → MDW 2026-12-04 13:01:00.

2026-12-04 · one way · Axel-exclusive $190.00

• Delta Air Lines DL1676 / DL1728: SAT 2026-12-04 11:00:00 → MDW 2026-12-04 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2026-12-04 11:00:00 → ATL 2026-12-04 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2026-12-04 15:25:00 → MDW 2026-12-04 16:18:00.

2026-12-06 · one way · Axel-exclusive $190.00

• Delta Air Lines DL2497 / DL4688: SAT 2026-12-06 05:25:00 → MDW 2026-12-06 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-12-06 05:25:00 → DTW 2026-12-06 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-12-06 12:44:00 → MDW 2026-12-06 13:01:00.

2026-12-06 · one way · Axel-exclusive $190.00

• Delta Air Lines DL1676 / DL1728: SAT 2026-12-06 11:00:00 → MDW 2026-12-06 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2026-12-06 11:00:00 → ATL 2026-12-06 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2026-12-06 15:25:00 → MDW 2026-12-06 16:18:00.

2026-12-05 · one way · Axel-exclusive $190.00

• Delta Air Lines DL1676 / DL1728: SAT 2026-12-05 11:00:00 → MDW 2026-12-05 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2026-12-05 11:00:00 → ATL 2026-12-05 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2026-12-05 15:25:00 → MDW 2026-12-05 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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