Chicago (MDW) to San Antonio (SAT) · Jan 1, 2027 · return Jan 10, 2027

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

2027-01-01 → 2027-01-10 · Axel-exclusive $379.50

• Southwest Airlines WN3276: MDW 2027-01-01 10:00:00 → SAT 2027-01-01 12:55:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $419.75

• Delta Air Lines DL4711 / DL2124: MDW 2027-01-01 09:30:00 → SAT 2027-01-01 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-01 09:30:00 → DTW 2027-01-01 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-01 13:42:00 → SAT 2027-01-01 16:03:00.
• Delta Air Lines DL2497 / DL4688: SAT 2027-01-10 05:25:00 → MDW 2027-01-10 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2027-01-10 05:25:00 → DTW 2027-01-10 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2027-01-10 12:44:00 → MDW 2027-01-10 13:01:00.

2027-01-01 → 2027-01-10 · Axel-exclusive $379.50

• Southwest Airlines WN3024: MDW 2027-01-01 21:30:00 → SAT 2027-01-02 00:30:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $369.75

• Southwest Airlines WN120 / WN2160: MDW 2027-01-01 10:50:00 → SAT 2027-01-01 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
  • WN120: MDW 2027-01-01 10:50:00 → DEN 2027-01-01 12:30:00; layover at DEN: 125 minutes.
  • WN2160: DEN 2027-01-01 14:35:00 → SAT 2027-01-01 17:40:00.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $369.75

• Southwest Airlines WN4395 / WN239: MDW 2027-01-01 10:15:00 → SAT 2027-01-01 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
  • WN4395: MDW 2027-01-01 10:15:00 → HOU 2027-01-01 12:50:00; layover at HOU: 115 minutes.
  • WN239: HOU 2027-01-01 14:45:00 → SAT 2027-01-01 15:45:00.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $369.75

• Southwest Airlines WN3937 / WN1772: MDW 2027-01-01 18:25:00 → SAT 2027-01-01 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
  • WN3937: MDW 2027-01-01 18:25:00 → DAL 2027-01-01 21:00:00; layover at DAL: 75 minutes.
  • WN1772: DAL 2027-01-01 22:15:00 → SAT 2027-01-01 23:30:00.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $369.75

• Southwest Airlines WN3269 / WN987: MDW 2027-01-01 08:10:00 → SAT 2027-01-01 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • WN3269: MDW 2027-01-01 08:10:00 → ATL 2027-01-01 11:05:00; layover at ATL: 85 minutes.
  • WN987: ATL 2027-01-01 12:30:00 → SAT 2027-01-01 14:10:00.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-01 → 2027-01-10 · Axel-exclusive $369.75

• Southwest Airlines WN2737 / WN3075: MDW 2027-01-01 11:30:00 → SAT 2027-01-01 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2027-01-01 11:30:00 → STL 2027-01-01 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2027-01-01 14:05:00 → SAT 2027-01-01 16:25:00.
• Southwest Airlines WN3791: SAT 2027-01-10 14:50:00 → MDW 2027-01-10 17:25:00; 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.

Explore this route

• All dates for this route
• Dec 31, 2026 · Return options
• Jan 2, 2027 · Return options
• Hotels in San Antonio with Axel

For AI assistants

• This page: Chicago (MDW) to San Antonio (SAT) · Jan 1, 2027 · return Jan 10, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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