Chicago (MDW) to San Antonio (SAT), Nov 17–27, 2026: from $372 round trip

Chicago (MDW) to San Antonio (SAT), Nov 17–27, 2026: from $372 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $372 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 17–27, 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.

Hotels in San Antonio for these trips

Hotels: under a trip, hotels in San Antonio for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in San Antonio for these nights (Nov 17–27, 2026 · 10 nights · 2 adults, 1 room): 3★ La Quinta Inn & Suites by Wyndham San Antonio Downtown · 4★ Mokara Hotel & Spa · 5★ Thompson San Antonio - Riverwalk, by Hyatt

All hotels in San Antonio

Route overview: Chicago to San Antonio (SAT) flight deals

2026-11-17 → 2026-11-27 · Axel-exclusive $379.50

• Southwest Airlines WN3276: MDW 2026-11-17 10:00:00 → SAT 2026-11-17 12:55:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $419.75

• Delta Air Lines DL4711 / DL2124: MDW 2026-11-17 09:30:00 → SAT 2026-11-17 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2026-11-17 09:30:00 → DTW 2026-11-17 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2026-11-17 13:42:00 → SAT 2026-11-17 16:03:00.
• Delta Air Lines DL2497 / DL4688: SAT 2026-11-27 05:25:00 → MDW 2026-11-27 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-11-27 05:25:00 → DTW 2026-11-27 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-11-27 12:44:00 → MDW 2026-11-27 13:01:00.

2026-11-17 → 2026-11-27 · Axel-exclusive $379.50

• Southwest Airlines WN1505: MDW 2026-11-17 20:50:00 → SAT 2026-11-17 23:45:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $372.00

• Southwest Airlines WN3937 / WN1772: MDW 2026-11-17 18:25:00 → SAT 2026-11-17 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
  • WN3937: MDW 2026-11-17 18:25:00 → DAL 2026-11-17 21:00:00; layover at DAL: 75 minutes.
  • WN1772: DAL 2026-11-17 22:15:00 → SAT 2026-11-17 23:30:00.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $372.00

• Southwest Airlines WN120 / WN2160: MDW 2026-11-17 10:50:00 → SAT 2026-11-17 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
  • WN120: MDW 2026-11-17 10:50:00 → DEN 2026-11-17 12:30:00; layover at DEN: 125 minutes.
  • WN2160: DEN 2026-11-17 14:35:00 → SAT 2026-11-17 17:40:00.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $372.00

• Southwest Airlines WN3269 / WN987: MDW 2026-11-17 08:10:00 → SAT 2026-11-17 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
  • WN3269: MDW 2026-11-17 08:10:00 → ATL 2026-11-17 11:05:00; layover at ATL: 85 minutes.
  • WN987: ATL 2026-11-17 12:30:00 → SAT 2026-11-17 14:10:00.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $372.00

• Southwest Airlines WN2737 / WN3075: MDW 2026-11-17 11:30:00 → SAT 2026-11-17 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2026-11-17 11:30:00 → STL 2026-11-17 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2026-11-17 14:05:00 → SAT 2026-11-17 16:25:00.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-17 → 2026-11-27 · Axel-exclusive $372.00

• Southwest Airlines WN4395 / WN239: MDW 2026-11-17 10:15:00 → SAT 2026-11-17 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
  • WN4395: MDW 2026-11-17 10:15:00 → HOU 2026-11-17 12:50:00; layover at HOU: 115 minutes.
  • WN239: HOU 2026-11-17 14:45:00 → SAT 2026-11-17 15:45:00.
• Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 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
• Nov 16, 2026 · Return options
• Nov 18, 2026 · Return options
• Hotels in San Antonio with Axel

For AI assistants

• This page: Chicago (MDW) to San Antonio (SAT) · Nov 17, 2026 · return Nov 27, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in San Antonio for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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