San Antonio (SAT) to Chicago (MDW), Nov 17–24, 2026: from $347 round trip
San Antonio (SAT) to Chicago (MDW), Nov 17–24, 2026: from $347 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $347 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 17–24, 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN2348 / WN3276 | 09:50:00→12:20:00 2h 30m nonstop · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $356.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Delta Air Lines | DL1676 + DL1728 / DL4711 + DL2124 | 11:00:00→16:18:00 5h 18m 1 stop via ATL · 09:30:00→16:03:00 6h 33m 1 stop via DTW | Axel-exclusive $414.00 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN3791 / WN3276 | 14:50:00→17:25:00 2h 35m nonstop · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $356.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN2991 + WN1005 / WN3276 | 07:10:00→12:55:00 5h 45m 1 stop via BNA · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $346.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN4494 + WN2134 / WN3276 | 13:00:00→19:40:00 6h 40m 1 stop via HOU · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $346.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN3801 + WN4175 / WN3276 | 15:20:00→20:00:00 4h 40m 1 stop via STL · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $346.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Southwest Airlines | WN1506 + WN1433 / WN3276 | 14:35:00→21:00:00 6h 25m 1 stop via DAL · 10:00:00→12:55:00 2h 55m nonstop | Axel-exclusive $346.50 | 2026-10-29T02:06:15Z |
| 2026-11-17 → 2026-11-24 | Delta Air Lines | DL2497 + DL4688 / DL4711 + DL2124 | 05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW | Axel-exclusive $414.00 | 2026-10-29T02:06:15Z |
Route overview: San Antonio to Chicago (MDW) flight deals
2026-11-17 → 2026-11-24 · Axel-exclusive $356.50
- Southwest Airlines WN2348: SAT 2026-11-17 09:50:00 → MDW 2026-11-17 12:20:00; nonstop; 150 minutes. Local airport times.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $414.00
- Delta Air Lines DL1676 / DL1728: SAT 2026-11-17 11:00:00 → MDW 2026-11-17 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
- DL1676: SAT 2026-11-17 11:00:00 → ATL 2026-11-17 14:17:00; layover at ATL: 68 minutes.
- DL1728: ATL 2026-11-17 15:25:00 → MDW 2026-11-17 16:18:00.
- Delta Air Lines DL4711 / DL2124: MDW 2026-11-24 09:30:00 → SAT 2026-11-24 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2026-11-24 09:30:00 → DTW 2026-11-24 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2026-11-24 13:42:00 → SAT 2026-11-24 16:03:00.
2026-11-17 → 2026-11-24 · Axel-exclusive $356.50
- Southwest Airlines WN3791: SAT 2026-11-17 14:50:00 → MDW 2026-11-17 17:25:00; nonstop; 155 minutes. Local airport times.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $346.50
- Southwest Airlines WN2991 / WN1005: SAT 2026-11-17 07:10:00 → MDW 2026-11-17 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
- WN2991: SAT 2026-11-17 07:10:00 → BNA 2026-11-17 09:25:00; layover at BNA: 120 minutes.
- WN1005: BNA 2026-11-17 11:25:00 → MDW 2026-11-17 12:55:00.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $346.50
- Southwest Airlines WN4494 / WN2134: SAT 2026-11-17 13:00:00 → MDW 2026-11-17 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
- WN4494: SAT 2026-11-17 13:00:00 → HOU 2026-11-17 13:55:00; layover at HOU: 200 minutes.
- WN2134: HOU 2026-11-17 17:15:00 → MDW 2026-11-17 19:40:00.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $346.50
- Southwest Airlines WN3801 / WN4175: SAT 2026-11-17 15:20:00 → MDW 2026-11-17 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2026-11-17 15:20:00 → STL 2026-11-17 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2026-11-17 18:55:00 → MDW 2026-11-17 20:00:00.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $346.50
- Southwest Airlines WN1506 / WN1433: SAT 2026-11-17 14:35:00 → MDW 2026-11-17 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
- WN1506: SAT 2026-11-17 14:35:00 → DAL 2026-11-17 15:40:00; layover at DAL: 190 minutes.
- WN1433: DAL 2026-11-17 18:50:00 → MDW 2026-11-17 21:00:00.
- Southwest Airlines WN3276: MDW 2026-11-24 10:00:00 → SAT 2026-11-24 12:55:00; nonstop; 175 minutes. Local airport times.
2026-11-17 → 2026-11-24 · Axel-exclusive $414.00
- Delta Air Lines DL2497 / DL4688: SAT 2026-11-17 05:25:00 → MDW 2026-11-17 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2026-11-17 05:25:00 → DTW 2026-11-17 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2026-11-17 12:44:00 → MDW 2026-11-17 13:01:00.
- Delta Air Lines DL4711 / DL2124: MDW 2026-11-24 09:30:00 → SAT 2026-11-24 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2026-11-24 09:30:00 → DTW 2026-11-24 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2026-11-24 13:42:00 → SAT 2026-11-24 16:03:00.
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