San Antonio (SAT) to Chicago (MDW), Nov 26–28, 2026: from $390 round trip

Lowest published fare: $390 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 26–28, 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

2026-11-26 → 2026-11-28 · Axel-exclusive $403.00

• Southwest Airlines WN3791: SAT 2026-11-26 14:50:00 → MDW 2026-11-26 17:25:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $468.00

• Delta Air Lines DL1676 / DL1728: SAT 2026-11-26 11:00:00 → MDW 2026-11-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2026-11-26 11:00:00 → ATL 2026-11-26 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2026-11-26 15:25:00 → MDW 2026-11-26 16:18:00.
• Delta Air Lines DL4711 / DL2124: MDW 2026-11-28 09:30:00 → SAT 2026-11-28 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2026-11-28 09:30:00 → DTW 2026-11-28 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2026-11-28 13:42:00 → SAT 2026-11-28 16:03:00.

2026-11-26 → 2026-11-28 · Axel-exclusive $403.00

• Southwest Airlines WN2348: SAT 2026-11-26 09:50:00 → MDW 2026-11-26 12:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $390.00

• Southwest Airlines WN3801 / WN4175: SAT 2026-11-26 15:20:00 → MDW 2026-11-26 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2026-11-26 15:20:00 → STL 2026-11-26 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2026-11-26 18:55:00 → MDW 2026-11-26 20:00:00.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $390.00

• Southwest Airlines WN2991 / WN1005: SAT 2026-11-26 07:10:00 → MDW 2026-11-26 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2026-11-26 07:10:00 → BNA 2026-11-26 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2026-11-26 11:25:00 → MDW 2026-11-26 12:55:00.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $390.00

• Southwest Airlines WN1506 / WN1433: SAT 2026-11-26 14:35:00 → MDW 2026-11-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
  • WN1506: SAT 2026-11-26 14:35:00 → DAL 2026-11-26 15:40:00; layover at DAL: 190 minutes.
  • WN1433: DAL 2026-11-26 18:50:00 → MDW 2026-11-26 21:00:00.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $390.00

• Southwest Airlines WN4494 / WN2134: SAT 2026-11-26 13:00:00 → MDW 2026-11-26 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2026-11-26 13:00:00 → HOU 2026-11-26 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2026-11-26 17:15:00 → MDW 2026-11-26 19:40:00.
• Southwest Airlines WN3024: MDW 2026-11-28 21:40:00 → SAT 2026-11-29 00:35:00; nonstop; 175 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $468.00

• Delta Air Lines DL2497 / DL4688: SAT 2026-11-26 05:25:00 → MDW 2026-11-26 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-11-26 05:25:00 → DTW 2026-11-26 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-11-26 12:44:00 → MDW 2026-11-26 13:01:00.
• Delta Air Lines DL4711 / DL2124: MDW 2026-11-28 09:30:00 → SAT 2026-11-28 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2026-11-28 09:30:00 → DTW 2026-11-28 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2026-11-28 13:42:00 → SAT 2026-11-28 16:03:00.

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.

Explore this route

• All dates for this route
• Nov 25, 2026 · Return options
• Nov 27, 2026 · Return options
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For AI assistants

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