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Chicago → San Antonio

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MDW → SAT1 adulteconomy

22 flight options · 2 airlines

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Show 6 more flights

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT

One-way 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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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 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)
2026-11-20 · one waySouthwest AirlinesWN3276$227.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3276 / WN2348$379.502026-10-29T01:29:13Z
2026-11-20 · one wayDelta Air LinesDL4711 + DL2124$253.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Delta Air LinesDL4711 + DL2124 / DL2497 + DL4688$419.752026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3937 + WN1772 / WN3801 + WN4175$409.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1505$227.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1505 / WN2348$379.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3937 + WN1772$214.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4395 + WN239$214.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2737 + WN3075$214.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN120 + WN2160$214.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3269 + WN987$214.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3269 + WN987 / WN2348$369.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4395 + WN239 / WN2348$369.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3937 + WN1772 / WN2348$369.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN120 + WN2160 / WN2348$369.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2737 + WN3075 / WN2348$369.752026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4395 + WN239 / WN3801 + WN4175$409.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3269 + WN987 / WN3801 + WN4175$409.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2737 + WN3075 / WN3801 + WN4175$409.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1505 / WN3801 + WN4175$419.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Delta Air LinesDL4711 + DL2124 / DL2497 + DL4688$474.502026-10-29T01:29:13Z

2026-11-20 · one way · $227.50

  • Southwest Airlines WN3276: MDW 2026-11-20 10:00:00 → SAT 2026-11-20 12:55:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $379.50

  • Southwest Airlines WN3276: MDW 2026-11-27 10:00:00 → SAT 2026-11-27 12:55:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $253.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-11-20 09:30:00 → SAT 2026-11-20 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-11-20 09:30:00 → DTW 2026-11-20 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-11-20 13:42:00 → SAT 2026-11-20 16:03:00.

2026-11-27 → 2026-12-04 · $419.75

  • Delta Air Lines DL4711 / DL2124: MDW 2026-11-27 09:30:00 → SAT 2026-11-27 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-11-27 09:30:00 → DTW 2026-11-27 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-11-27 13:42:00 → SAT 2026-11-27 16:03:00.
  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-04 05:25:00 → MDW 2026-12-04 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-04 05:25:00 → DTW 2026-12-04 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-04 12:44:00 → MDW 2026-12-04 13:01:00.

2026-11-20 → 2026-11-23 · $409.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-11-20 18:25:00 → SAT 2026-11-20 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-11-20 18:25:00 → DAL 2026-11-20 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-11-20 22:15:00 → SAT 2026-11-20 23:30:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-23 15:20:00 → MDW 2026-11-23 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-23 15:20:00 → STL 2026-11-23 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-23 18:55:00 → MDW 2026-11-23 20:00:00.

2026-11-20 · one way · $227.50

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

2026-11-27 → 2026-12-04 · $379.50

  • Southwest Airlines WN1505: MDW 2026-11-27 20:50:00 → SAT 2026-11-27 23:45:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $214.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-11-20 18:25:00 → SAT 2026-11-20 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-11-20 18:25:00 → DAL 2026-11-20 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-11-20 22:15:00 → SAT 2026-11-20 23:30:00.

2026-11-20 · one way · $214.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-11-20 10:15:00 → SAT 2026-11-20 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-11-20 14:45:00 → SAT 2026-11-20 15:45:00.

2026-11-20 · one way · $214.50

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

2026-11-20 · one way · $214.50

  • Southwest Airlines WN120 / WN2160: MDW 2026-11-20 10:50:00 → SAT 2026-11-20 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-11-20 10:50:00 → DEN 2026-11-20 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-11-20 14:35:00 → SAT 2026-11-20 17:40:00.

2026-11-20 · one way · $214.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-11-20 08:10:00 → SAT 2026-11-20 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-11-20 08:10:00 → ATL 2026-11-20 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-11-20 12:30:00 → SAT 2026-11-20 14:10:00.

2026-11-27 → 2026-12-04 · $369.75

  • Southwest Airlines WN3269 / WN987: MDW 2026-11-27 08:10:00 → SAT 2026-11-27 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-11-27 08:10:00 → ATL 2026-11-27 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-11-27 12:30:00 → SAT 2026-11-27 14:10:00.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $369.75

  • Southwest Airlines WN4395 / WN239: MDW 2026-11-27 10:15:00 → SAT 2026-11-27 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-11-27 10:15:00 → HOU 2026-11-27 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-11-27 14:45:00 → SAT 2026-11-27 15:45:00.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $369.75

  • Southwest Airlines WN3937 / WN1772: MDW 2026-11-27 18:25:00 → SAT 2026-11-27 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-11-27 18:25:00 → DAL 2026-11-27 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-11-27 22:15:00 → SAT 2026-11-27 23:30:00.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $369.75

  • Southwest Airlines WN120 / WN2160: MDW 2026-11-27 10:50:00 → SAT 2026-11-27 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-11-27 10:50:00 → DEN 2026-11-27 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-11-27 14:35:00 → SAT 2026-11-27 17:40:00.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $369.75

  • Southwest Airlines WN2737 / WN3075: MDW 2026-11-27 11:30:00 → SAT 2026-11-27 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-11-27 11:30:00 → STL 2026-11-27 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-11-27 14:05:00 → SAT 2026-11-27 16:25:00.
  • Southwest Airlines WN2348: SAT 2026-12-04 06:25:00 → MDW 2026-12-04 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $409.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-11-20 10:15:00 → SAT 2026-11-20 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-11-20 14:45:00 → SAT 2026-11-20 15:45:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-23 15:20:00 → MDW 2026-11-23 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-23 15:20:00 → STL 2026-11-23 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-23 18:55:00 → MDW 2026-11-23 20:00:00.

2026-11-20 → 2026-11-23 · $409.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-11-20 08:10:00 → SAT 2026-11-20 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-11-20 08:10:00 → ATL 2026-11-20 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-11-20 12:30:00 → SAT 2026-11-20 14:10:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-23 15:20:00 → MDW 2026-11-23 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-23 15:20:00 → STL 2026-11-23 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-23 18:55:00 → MDW 2026-11-23 20:00:00.

2026-11-20 → 2026-11-23 · $409.50

  • Southwest Airlines WN2737 / WN3075: MDW 2026-11-20 11:30:00 → SAT 2026-11-20 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-11-20 11:30:00 → STL 2026-11-20 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-11-20 14:05:00 → SAT 2026-11-20 16:25:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-23 15:20:00 → MDW 2026-11-23 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-23 15:20:00 → STL 2026-11-23 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-23 18:55:00 → MDW 2026-11-23 20:00:00.

2026-11-20 → 2026-11-23 · $419.25

  • Southwest Airlines WN1505: MDW 2026-11-20 20:50:00 → SAT 2026-11-20 23:45:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-23 15:20:00 → MDW 2026-11-23 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-23 15:20:00 → STL 2026-11-23 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-23 18:55:00 → MDW 2026-11-23 20:00:00.

2026-11-20 → 2026-11-23 · $474.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-11-20 09:30:00 → SAT 2026-11-20 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-11-20 09:30:00 → DTW 2026-11-20 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-11-20 13:42:00 → SAT 2026-11-20 16:03:00.
  • Delta Air Lines DL2497 / DL4688: SAT 2026-11-23 05:25:00 → MDW 2026-11-23 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-11-23 05:25:00 → DTW 2026-11-23 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-11-23 12:44:00 → MDW 2026-11-23 13:01:00.

More dates for this route