Chicago (MDW) to San Antonio (SAT), Jan 22–24, 2027: from $165 one way

Chicago (MDW) to San Antonio (SAT), Jan 22–24, 2027: from $165 one way on Axel, checked Oct 29, 2026. Lowest published fare: $165 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 22, 2027, 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 San Antonio (SAT) flight deals

2027-01-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3276: MDW 2027-01-22 10:00:00 → SAT 2027-01-22 12:55:00; nonstop; 175 minutes. Local airport times.

2027-01-23 · one way · Axel-exclusive $195.00

• Delta Air Lines DL4711 / DL2124: MDW 2027-01-23 09:30:00 → SAT 2027-01-23 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-23 09:30:00 → DTW 2027-01-23 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-23 13:42:00 → SAT 2027-01-23 16:03:00.

2027-01-24 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3276: MDW 2027-01-24 10:00:00 → SAT 2027-01-24 12:55:00; nonstop; 175 minutes. Local airport times.

2027-01-24 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3024: MDW 2027-01-24 21:30:00 → SAT 2027-01-25 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-23 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3276: MDW 2027-01-23 10:00:00 → SAT 2027-01-23 12:55:00; nonstop; 175 minutes. Local airport times.

2027-01-23 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3024: MDW 2027-01-23 21:40:00 → SAT 2027-01-24 00:35:00; nonstop; 175 minutes. Local airport times.

2027-01-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3024: MDW 2027-01-22 21:30:00 → SAT 2027-01-23 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-22 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2737 / WN3075: MDW 2027-01-22 11:30:00 → SAT 2027-01-22 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2027-01-22 11:30:00 → STL 2027-01-22 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2027-01-22 14:05:00 → SAT 2027-01-22 16:25:00.

2027-01-24 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2737 / WN3075: MDW 2027-01-24 11:30:00 → SAT 2027-01-24 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2027-01-24 11:30:00 → STL 2027-01-24 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2027-01-24 14:05:00 → SAT 2027-01-24 16:25:00.

2027-01-22 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4395 / WN239: MDW 2027-01-22 10:15:00 → SAT 2027-01-22 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
  • WN4395: MDW 2027-01-22 10:15:00 → HOU 2027-01-22 12:50:00; layover at HOU: 115 minutes.
  • WN239: HOU 2027-01-22 14:45:00 → SAT 2027-01-22 15:45:00.

2027-01-23 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2737 / WN3075: MDW 2027-01-23 11:30:00 → SAT 2027-01-23 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2027-01-23 11:30:00 → STL 2027-01-23 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2027-01-23 14:05:00 → SAT 2027-01-23 16:25:00.

2027-01-22 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3269 / WN987: MDW 2027-01-22 08:10:00 → SAT 2027-01-22 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • WN3269: MDW 2027-01-22 08:10:00 → ATL 2027-01-22 11:05:00; layover at ATL: 85 minutes.
  • WN987: ATL 2027-01-22 12:30:00 → SAT 2027-01-22 14:10:00.

2027-01-22 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3937 / WN1772: MDW 2027-01-22 18:25:00 → SAT 2027-01-22 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
  • WN3937: MDW 2027-01-22 18:25:00 → DAL 2027-01-22 21:00:00; layover at DAL: 75 minutes.
  • WN1772: DAL 2027-01-22 22:15:00 → SAT 2027-01-22 23:30:00.

2027-01-23 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4395 / WN239: MDW 2027-01-23 10:15:00 → SAT 2027-01-23 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
  • WN4395: MDW 2027-01-23 10:15:00 → HOU 2027-01-23 12:50:00; layover at HOU: 115 minutes.
  • WN239: HOU 2027-01-23 14:45:00 → SAT 2027-01-23 15:45:00.

2027-01-24 · one way · Axel-exclusive $165.00

• Southwest Airlines WN120 / WN2160: MDW 2027-01-24 10:50:00 → SAT 2027-01-24 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
  • WN120: MDW 2027-01-24 10:50:00 → DEN 2027-01-24 12:30:00; layover at DEN: 125 minutes.
  • WN2160: DEN 2027-01-24 14:35:00 → SAT 2027-01-24 17:40:00.

2027-01-23 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3269 / WN987: MDW 2027-01-23 08:10:00 → SAT 2027-01-23 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • WN3269: MDW 2027-01-23 08:10:00 → ATL 2027-01-23 11:05:00; layover at ATL: 85 minutes.
  • WN987: ATL 2027-01-23 12:30:00 → SAT 2027-01-23 14:10:00.

2027-01-23 · one way · Axel-exclusive $165.00

• Southwest Airlines WN120 / WN2160: MDW 2027-01-23 10:50:00 → SAT 2027-01-23 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
  • WN120: MDW 2027-01-23 10:50:00 → DEN 2027-01-23 12:30:00; layover at DEN: 125 minutes.
  • WN2160: DEN 2027-01-23 14:35:00 → SAT 2027-01-23 17:40:00.

2027-01-24 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4395 / WN239: MDW 2027-01-24 10:15:00 → SAT 2027-01-24 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
  • WN4395: MDW 2027-01-24 10:15:00 → HOU 2027-01-24 12:50:00; layover at HOU: 115 minutes.
  • WN239: HOU 2027-01-24 14:45:00 → SAT 2027-01-24 15:45:00.

2027-01-24 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3269 / WN987: MDW 2027-01-24 08:10:00 → SAT 2027-01-24 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • WN3269: MDW 2027-01-24 08:10:00 → ATL 2027-01-24 11:05:00; layover at ATL: 85 minutes.
  • WN987: ATL 2027-01-24 12:30:00 → SAT 2027-01-24 14:10:00.

2027-01-23 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3937 / WN1772: MDW 2027-01-23 18:25:00 → SAT 2027-01-23 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
  • WN3937: MDW 2027-01-23 18:25:00 → DAL 2027-01-23 21:00:00; layover at DAL: 75 minutes.
  • WN1772: DAL 2027-01-23 22:15:00 → SAT 2027-01-23 23:30:00.

2027-01-22 · one way · Axel-exclusive $165.00

• Southwest Airlines WN120 / WN2160: MDW 2027-01-22 10:50:00 → SAT 2027-01-22 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
  • WN120: MDW 2027-01-22 10:50:00 → DEN 2027-01-22 12:30:00; layover at DEN: 125 minutes.
  • WN2160: DEN 2027-01-22 14:35:00 → SAT 2027-01-22 17:40:00.

2027-01-24 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3937 / WN1772: MDW 2027-01-24 18:25:00 → SAT 2027-01-24 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
  • WN3937: MDW 2027-01-24 18:25:00 → DAL 2027-01-24 21:00:00; layover at DAL: 75 minutes.
  • WN1772: DAL 2027-01-24 22:15:00 → SAT 2027-01-24 23:30:00.

2027-01-22 · one way · Axel-exclusive $195.00

• Delta Air Lines DL4711 / DL2124: MDW 2027-01-22 09:30:00 → SAT 2027-01-22 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-22 09:30:00 → DTW 2027-01-22 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-22 13:42:00 → SAT 2027-01-22 16:03:00.

2027-01-24 · one way · Axel-exclusive $195.00

• Delta Air Lines DL4711 / DL2124: MDW 2027-01-24 09:30:00 → SAT 2027-01-24 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-24 09:30:00 → DTW 2027-01-24 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-24 13:42:00 → SAT 2027-01-24 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.

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