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Chicago → San Antonio

Jan 21, 2027 · return Jan 25, 2027

MDW → SAT1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Thu, Jan 21 – Mon, Jan 25

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

Thu, Jan 21 – Mon, Jan 25

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

Thu, Jan 21 – Mon, Jan 25

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

Thu, Jan 21 – Mon, Jan 25

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

Thu, Jan 21 – Mon, Jan 25

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Mon, Jan 25

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

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 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)
2027-01-21 → 2027-01-25Southwest AirlinesWN4395 + WN239 / WN3801 + WN4175$315.002026-10-29T01:29:13Z
2027-01-21 → 2027-01-25Southwest AirlinesWN3937 + WN1772 / WN3801 + WN4175$315.002026-10-29T01:29:13Z
2027-01-21 → 2027-01-25Southwest AirlinesWN2737 + WN3075 / WN3801 + WN4175$315.002026-10-29T01:29:13Z
2027-01-21 → 2027-01-25Southwest AirlinesWN3269 + WN987 / WN3801 + WN4175$315.002026-10-29T01:29:13Z
2027-01-21 → 2027-01-25Southwest AirlinesWN120 + WN2160 / WN3801 + WN4175$315.002026-10-29T01:29:13Z
2027-01-21 → 2027-01-25Southwest AirlinesWN1505 / WN3801 + WN4175$322.502026-10-29T01:29:13Z

2027-01-21 → 2027-01-25 · $315.00

  • Southwest Airlines WN4395 / WN239: MDW 2027-01-21 10:15:00 → SAT 2027-01-21 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2027-01-21 10:15:00 → HOU 2027-01-21 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2027-01-21 14:45:00 → SAT 2027-01-21 15:45:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

2027-01-21 → 2027-01-25 · $315.00

  • Southwest Airlines WN3937 / WN1772: MDW 2027-01-21 18:25:00 → SAT 2027-01-21 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2027-01-21 18:25:00 → DAL 2027-01-21 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2027-01-21 22:15:00 → SAT 2027-01-21 23:30:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

2027-01-21 → 2027-01-25 · $315.00

  • Southwest Airlines WN2737 / WN3075: MDW 2027-01-21 11:30:00 → SAT 2027-01-21 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2027-01-21 14:05:00 → SAT 2027-01-21 16:25:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

2027-01-21 → 2027-01-25 · $315.00

  • Southwest Airlines WN3269 / WN987: MDW 2027-01-21 08:10:00 → SAT 2027-01-21 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2027-01-21 08:10:00 → ATL 2027-01-21 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2027-01-21 12:30:00 → SAT 2027-01-21 14:10:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

2027-01-21 → 2027-01-25 · $315.00

  • Southwest Airlines WN120 / WN2160: MDW 2027-01-21 10:50:00 → SAT 2027-01-21 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2027-01-21 10:50:00 → DEN 2027-01-21 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2027-01-21 14:35:00 → SAT 2027-01-21 17:40:00.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

2027-01-21 → 2027-01-25 · $322.50

  • Southwest Airlines WN1505: MDW 2027-01-21 20:50:00 → SAT 2027-01-21 23:45:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-25 15:20:00 → MDW 2027-01-25 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-25 15:20:00 → STL 2027-01-25 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-25 18:55:00 → MDW 2027-01-25 20:00:00.

More dates for this route