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Chicago → San Antonio

Dec 21, 2026 · return Dec 24, 2026

MDW → SAT1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 24

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT
Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

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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More dates

All dates for this routeNov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-24Southwest AirlinesWN3024 / WN2348$429.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Delta Air LinesDL4711 + DL2124 / DL2497 + DL4688$474.502026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN3276 / WN2348$429.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN3937 + WN1772 / WN2348$419.252026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN4395 + WN239 / WN2348$419.252026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN3269 + WN987 / WN2348$419.252026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN120 + WN2160 / WN2348$419.252026-10-29T01:29:13Z
2026-12-21 → 2026-12-24Southwest AirlinesWN2737 + WN3075 / WN2348$419.252026-10-29T01:29:13Z

2026-12-21 → 2026-12-24 · $429.00

  • Southwest Airlines WN3024: MDW 2026-12-21 21:30:00 → SAT 2026-12-22 00:30:00; nonstop; 180 minutes. Local airport times.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $474.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-21 09:30:00 → SAT 2026-12-21 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-21 09:30:00 → DTW 2026-12-21 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-21 13:42:00 → SAT 2026-12-21 16:03:00.
  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-24 05:25:00 → MDW 2026-12-24 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-24 05:25:00 → DTW 2026-12-24 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-24 12:44:00 → MDW 2026-12-24 13:01:00.

2026-12-21 → 2026-12-24 · $429.00

  • Southwest Airlines WN3276: MDW 2026-12-21 10:00:00 → SAT 2026-12-21 12:55:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $419.25

  • Southwest Airlines WN3937 / WN1772: MDW 2026-12-21 18:25:00 → SAT 2026-12-21 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-12-21 18:25:00 → DAL 2026-12-21 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-12-21 22:15:00 → SAT 2026-12-21 23:30:00.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $419.25

  • Southwest Airlines WN4395 / WN239: MDW 2026-12-21 10:15:00 → SAT 2026-12-21 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-12-21 10:15:00 → HOU 2026-12-21 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-12-21 14:45:00 → SAT 2026-12-21 15:45:00.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $419.25

  • Southwest Airlines WN3269 / WN987: MDW 2026-12-21 08:10:00 → SAT 2026-12-21 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-12-21 08:10:00 → ATL 2026-12-21 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-12-21 12:30:00 → SAT 2026-12-21 14:10:00.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $419.25

  • Southwest Airlines WN120 / WN2160: MDW 2026-12-21 10:50:00 → SAT 2026-12-21 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-12-21 10:50:00 → DEN 2026-12-21 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-12-21 14:35:00 → SAT 2026-12-21 17:40:00.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $419.25

  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-21 11:30:00 → SAT 2026-12-21 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-21 11:30:00 → STL 2026-12-21 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-21 14:05:00 → SAT 2026-12-21 16:25:00.
  • Southwest Airlines WN2348: SAT 2026-12-24 06:25:00 → MDW 2026-12-24 08:55:00; nonstop; 150 minutes. Local airport times.

More dates for this route