San Antonio (SAT) to Chicago (MDW), Nov 16–26, 2026: from $334 round trip

San Antonio (SAT) to Chicago (MDW), Nov 16–26, 2026: from $334 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $334 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 16–26, 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.

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

2026-11-16 → 2026-11-26 · Axel-exclusive $333.50

• Southwest Airlines WN2991 / WN1005: SAT 2026-11-16 07:10:00 → MDW 2026-11-16 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
  • WN2991: SAT 2026-11-16 07:10:00 → BNA 2026-11-16 09:25:00; layover at BNA: 120 minutes.
  • WN1005: BNA 2026-11-16 11:25:00 → MDW 2026-11-16 12:55:00.
• Southwest Airlines WN2737 / WN3075: MDW 2026-11-26 11:30:00 → SAT 2026-11-26 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2026-11-26 11:30:00 → STL 2026-11-26 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2026-11-26 14:05:00 → SAT 2026-11-26 16:25:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $414.00

• Delta Air Lines DL2497 / DL4688: SAT 2026-11-16 05:25:00 → MDW 2026-11-16 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
  • DL2497: SAT 2026-11-16 05:25:00 → DTW 2026-11-16 09:28:00; layover at DTW: 196 minutes.
  • DL4688: DTW 2026-11-16 12:44:00 → MDW 2026-11-16 13:01:00.
• Delta Air Lines DL4711 / DL2124: MDW 2026-11-26 09:30:00 → SAT 2026-11-26 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2026-11-26 09:30:00 → DTW 2026-11-26 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2026-11-26 13:42:00 → SAT 2026-11-26 16:03:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $333.50

• Southwest Airlines WN4494 / WN2134: SAT 2026-11-16 13:00:00 → MDW 2026-11-16 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
  • WN4494: SAT 2026-11-16 13:00:00 → HOU 2026-11-16 13:55:00; layover at HOU: 200 minutes.
  • WN2134: HOU 2026-11-16 17:15:00 → MDW 2026-11-16 19:40:00.
• Southwest Airlines WN2737 / WN3075: MDW 2026-11-26 11:30:00 → SAT 2026-11-26 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2026-11-26 11:30:00 → STL 2026-11-26 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2026-11-26 14:05:00 → SAT 2026-11-26 16:25:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $333.50

• Southwest Airlines WN3801 / WN4175: SAT 2026-11-16 15:20:00 → MDW 2026-11-16 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
  • WN3801: SAT 2026-11-16 15:20:00 → STL 2026-11-16 17:20:00; layover at STL: 95 minutes.
  • WN4175: STL 2026-11-16 18:55:00 → MDW 2026-11-16 20:00:00.
• Southwest Airlines WN2737 / WN3075: MDW 2026-11-26 11:30:00 → SAT 2026-11-26 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2026-11-26 11:30:00 → STL 2026-11-26 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2026-11-26 14:05:00 → SAT 2026-11-26 16:25:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $343.50

• Southwest Airlines WN3791: SAT 2026-11-16 14:50:00 → MDW 2026-11-16 17:25:00; nonstop; 155 minutes. Local airport times.
• Southwest Airlines WN2737 / WN3075: MDW 2026-11-26 11:30:00 → SAT 2026-11-26 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
  • WN2737: MDW 2026-11-26 11:30:00 → STL 2026-11-26 12:40:00; layover at STL: 85 minutes.
  • WN3075: STL 2026-11-26 14:05:00 → SAT 2026-11-26 16:25:00.

2026-11-16 → 2026-11-26 · Axel-exclusive $414.00

• Delta Air Lines DL1676 / DL1728: SAT 2026-11-16 11:00:00 → MDW 2026-11-16 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
  • DL1676: SAT 2026-11-16 11:00:00 → ATL 2026-11-16 14:17:00; layover at ATL: 68 minutes.
  • DL1728: ATL 2026-11-16 15:25:00 → MDW 2026-11-16 16:18:00.
• Delta Air Lines DL4711 / DL2124: MDW 2026-11-26 09:30:00 → SAT 2026-11-26 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
  • DL4711: MDW 2026-11-26 09:30:00 → DTW 2026-11-26 11:45:00; layover at DTW: 117 minutes.
  • DL2124: DTW 2026-11-26 13:42:00 → SAT 2026-11-26 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.

Explore this route

• All dates for this route
• Nov 15, 2026 · Return options
• Nov 17, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Antonio (SAT) to Chicago (MDW) · Nov 16, 2026 · return Nov 26, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Antonio to Chicago (MDW) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue