San Antonio (SAT) to Chicago (MDW) · Jan 19, 2027 · return Jan 29, 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: San Antonio to Chicago (MDW) flight deals

2027-01-19 → 2027-01-29 · Axel-exclusive $310.00

• Southwest Airlines WN2348: SAT 2027-01-19 09:50:00 → MDW 2027-01-19 12:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $360.00

• Delta Air Lines DL2497 / DL4688: SAT 2027-01-19 05:25:00 → MDW 2027-01-19 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2027-01-19 05:25:00 → DTW 2027-01-19 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2027-01-19 12:44:00 → MDW 2027-01-19 13:01:00.
• Delta Air Lines DL4711 / DL2124: MDW 2027-01-29 09:30:00 → SAT 2027-01-29 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-29 09:30:00 → DTW 2027-01-29 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-29 13:42:00 → SAT 2027-01-29 16:03:00.

2027-01-19 → 2027-01-29 · Axel-exclusive $310.00

• Southwest Airlines WN2925: SAT 2027-01-19 15:15:00 → MDW 2027-01-19 17:50:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $300.00

• Southwest Airlines WN3801 / WN4175: SAT 2027-01-19 15:20:00 → MDW 2027-01-19 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2027-01-19 15:20:00 → STL 2027-01-19 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2027-01-19 18:55:00 → MDW 2027-01-19 20:00:00.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $300.00

• Southwest Airlines WN1506 / WN1433: SAT 2027-01-19 14:35:00 → MDW 2027-01-19 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
  • WN1506: SAT 2027-01-19 14:35:00 → DAL 2027-01-19 15:40:00; layover at DAL: 190 minutes.
  • WN1433: DAL 2027-01-19 18:50:00 → MDW 2027-01-19 21:00:00.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $300.00

• Southwest Airlines WN2991 / WN1005: SAT 2027-01-19 07:10:00 → MDW 2027-01-19 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2027-01-19 07:10:00 → BNA 2027-01-19 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2027-01-19 11:25:00 → MDW 2027-01-19 12:55:00.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $300.00

• Southwest Airlines WN4494 / WN2134: SAT 2027-01-19 13:00:00 → MDW 2027-01-19 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2027-01-19 13:00:00 → HOU 2027-01-19 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2027-01-19 17:15:00 → MDW 2027-01-19 19:40:00.
• Southwest Airlines WN3024: MDW 2027-01-29 21:30:00 → SAT 2027-01-30 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-19 → 2027-01-29 · Axel-exclusive $360.00

• Delta Air Lines DL1676 / DL1728: SAT 2027-01-19 11:00:00 → MDW 2027-01-19 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2027-01-19 11:00:00 → ATL 2027-01-19 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2027-01-19 15:25:00 → MDW 2027-01-19 16:18:00.
• Delta Air Lines DL4711 / DL2124: MDW 2027-01-29 09:30:00 → SAT 2027-01-29 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2027-01-29 09:30:00 → DTW 2027-01-29 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2027-01-29 13:42:00 → SAT 2027-01-29 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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