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

San Antonio → Chicago

Dec 28, 2026 · return Dec 29, 2026

SAT → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

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

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 28 – Tue, Dec 29

Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
2:35 pmSAT
6h 25m
DAL · 3h 10m
9:00 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
7:10 amSAT
5h 45m
BNA · 2h
12:55 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
1:00 pmSAT
6h 40m
HOU · 3h 20m
7:40 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

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

Round-trip total · 1 adult · Taxes included

Make this trip yours

SAT ⇄ MDW

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 routeDec 27, 2026 → Dec 28, 2026Dec 29, 2026 → Dec 30, 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: San Antonio to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-28 → 2026-12-29Southwest AirlinesWN2348 / WN1505$372.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124$432.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Southwest AirlinesWN3791 / WN1505$372.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Southwest AirlinesWN1506 + WN1433 / WN1505$360.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Southwest AirlinesWN2991 + WN1005 / WN1505$360.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Southwest AirlinesWN4494 + WN2134 / WN1505$360.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Southwest AirlinesWN3801 + WN4175 / WN1505$360.002026-10-29T02:06:15Z
2026-12-28 → 2026-12-29Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124$432.002026-10-29T02:06:15Z

2026-12-28 → 2026-12-29 · $372.00

  • Southwest Airlines WN2348: SAT 2026-12-28 06:25:00 → MDW 2026-12-28 08:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $432.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-28 05:25:00 → MDW 2026-12-28 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-28 05:25:00 → DTW 2026-12-28 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-28 12:44:00 → MDW 2026-12-28 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-29 09:30:00 → SAT 2026-12-29 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-29 09:30:00 → DTW 2026-12-29 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-29 13:42:00 → SAT 2026-12-29 16:03:00.

2026-12-28 → 2026-12-29 · $372.00

  • Southwest Airlines WN3791: SAT 2026-12-28 14:50:00 → MDW 2026-12-28 17:25:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $360.00

  • Southwest Airlines WN1506 / WN1433: SAT 2026-12-28 14:35:00 → MDW 2026-12-28 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2026-12-28 14:35:00 → DAL 2026-12-28 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2026-12-28 18:50:00 → MDW 2026-12-28 21:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $360.00

  • Southwest Airlines WN2991 / WN1005: SAT 2026-12-28 07:10:00 → MDW 2026-12-28 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
    • WN2991: SAT 2026-12-28 07:10:00 → BNA 2026-12-28 09:25:00; layover at BNA: 120 minutes.
    • WN1005: BNA 2026-12-28 11:25:00 → MDW 2026-12-28 12:55:00.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $360.00

  • Southwest Airlines WN4494 / WN2134: SAT 2026-12-28 13:00:00 → MDW 2026-12-28 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
    • WN4494: SAT 2026-12-28 13:00:00 → HOU 2026-12-28 13:55:00; layover at HOU: 200 minutes.
    • WN2134: HOU 2026-12-28 17:15:00 → MDW 2026-12-28 19:40:00.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $360.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-28 15:20:00 → MDW 2026-12-28 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-28 15:20:00 → STL 2026-12-28 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-28 18:55:00 → MDW 2026-12-28 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-29 20:50:00 → SAT 2026-12-29 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $432.00

  • Delta Air Lines DL1676 / DL1728: SAT 2026-12-28 11:00:00 → MDW 2026-12-28 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2026-12-28 11:00:00 → ATL 2026-12-28 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2026-12-28 15:25:00 → MDW 2026-12-28 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-29 09:30:00 → SAT 2026-12-29 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-29 09:30:00 → DTW 2026-12-29 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-29 13:42:00 → SAT 2026-12-29 16:03:00.

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For AI assistants

  • This page: San Antonio (SAT) to Chicago (MDW) · Dec 28, 2026 · return Dec 29, 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.
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  • 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.