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

Chicago → San Antonio

Dec 1, 2026 · return Dec 6, 2026

MDW → SAT1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Tue, Dec 1 – Sun, Dec 6

Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Delta Air Lines
11:00 amSAT
5h 18m
ATL · 1h 8m
4:18 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT
Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SAT

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeNov 30, 2026 → Dec 5, 2026Dec 2, 2026 → Dec 7, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-01 → 2026-12-06Southwest AirlinesWN1505 / WN3791$330.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Delta Air LinesDL4711 + DL2124 / DL1676 + DL1728$365.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN3276 / WN3791$330.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN3937 + WN1772 / WN3791$322.502026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN2737 + WN3075 / WN3791$322.502026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN120 + WN2160 / WN3791$322.502026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN4395 + WN239 / WN3791$322.502026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN3269 + WN987 / WN3791$322.502026-10-29T01:29:13Z

2026-12-01 → 2026-12-06 · $330.00

  • Southwest Airlines WN1505: MDW 2026-12-01 20:50:00 → SAT 2026-12-01 23:45:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $365.00

  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-01 09:30:00 → SAT 2026-12-01 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-01 09:30:00 → DTW 2026-12-01 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-01 13:42:00 → SAT 2026-12-01 16:03:00.
  • Delta Air Lines DL1676 / DL1728: SAT 2026-12-06 11:00:00 → MDW 2026-12-06 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2026-12-06 11:00:00 → ATL 2026-12-06 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2026-12-06 15:25:00 → MDW 2026-12-06 16:18:00.

2026-12-01 → 2026-12-06 · $330.00

  • Southwest Airlines WN3276: MDW 2026-12-01 10:00:00 → SAT 2026-12-01 12:55:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $322.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-12-01 18:25:00 → SAT 2026-12-01 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-12-01 18:25:00 → DAL 2026-12-01 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-12-01 22:15:00 → SAT 2026-12-01 23:30:00.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $322.50

  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-01 11:30:00 → SAT 2026-12-01 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-01 11:30:00 → STL 2026-12-01 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-01 14:05:00 → SAT 2026-12-01 16:25:00.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $322.50

  • Southwest Airlines WN120 / WN2160: MDW 2026-12-01 10:50:00 → SAT 2026-12-01 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-12-01 10:50:00 → DEN 2026-12-01 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-12-01 14:35:00 → SAT 2026-12-01 17:40:00.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $322.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-12-01 10:15:00 → SAT 2026-12-01 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-12-01 10:15:00 → HOU 2026-12-01 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-12-01 14:45:00 → SAT 2026-12-01 15:45:00.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $322.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-12-01 08:10:00 → SAT 2026-12-01 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-12-01 08:10:00 → ATL 2026-12-01 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-12-01 12:30:00 → SAT 2026-12-01 14:10:00.
  • Southwest Airlines WN3791: SAT 2026-12-06 14:50:00 → MDW 2026-12-06 17:25:00; nonstop; 155 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Antonio (SAT) · Dec 1, 2026 · return Dec 6, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • 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 Chicago to San Antonio (SAT) 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.