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

San Antonio → Chicago

Dec 21, 2026 · choose your return date

SAT → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

December 2026

Dec 21, 2026 · One waySouthwest AirlinesUp to 1 stop each way$201.50 Dec 21, 2026 · One wayDelta Air LinesUp to 1 stop each way$247.00 Dec 21, 2026 – Dec 22, 2026 · 1 nightSouthwest AirlinesUp to 1 stop each way$390.00 Dec 21, 2026 – Dec 22, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 23, 2026 · 2 nightsSouthwest AirlinesUp to 1 stop each way$390.00 Dec 21, 2026 – Dec 23, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 24, 2026 · 3 nightsSouthwest AirlinesUp to 1 stop each way$377.00 Dec 21, 2026 – Dec 24, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 25, 2026 · 4 nightsSouthwest AirlinesUp to 1 stop each way$390.00 Dec 21, 2026 – Dec 25, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 26, 2026 · 5 nightsSouthwest AirlinesUp to 1 stop each way$390.00 Dec 21, 2026 – Dec 26, 2026 · 5 nightsDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 27, 2026 · 6 nightsSouthwest AirlinesUp to 1 stop each way$390.00 Dec 21, 2026 – Dec 27, 2026 · 6 nightsDelta Air LinesUp to 1 stop each way$468.00 Dec 21, 2026 – Dec 28, 2026 · 7 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Dec 28, 2026 · 7 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Dec 29, 2026 · 8 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Dec 29, 2026 · 8 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Dec 30, 2026 · 9 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Dec 30, 2026 · 9 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Dec 31, 2026 · 10 nightsSouthwest AirlinesUp to 1 stop each way$362.50 Dec 21, 2026 – Dec 31, 2026 · 10 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Jan 1, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Jan 1, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Jan 2, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Jan 2, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Jan 3, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$374.50 Dec 21, 2026 – Jan 3, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$450.00 Dec 21, 2026 – Jan 4, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$343.50 Dec 21, 2026 – Jan 4, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$414.00

Flights for your trip

  1. Mon, Dec 21 · One way

    Southwest Airlines
    3:20 pmSAT
    4h 40m
    STL · 1h 35m
    8:00 pmMDW

    One-way total · 1 adult · Taxes included

  2. Mon, Dec 21 · One way

    Delta Air Lines
    5:25 amSAT
    7h 36m
    DTW · 3h 16m
    1:01 pmMDW

    One-way total · 1 adult · Taxes included

  3. Mon, Dec 21 – Tue, Dec 22

    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

  4. Mon, Dec 21 – Tue, Dec 22

    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

  5. Mon, Dec 21 – Wed, Dec 23

    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

  6. Mon, Dec 21 – Wed, Dec 23

    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

  7. Mon, Dec 21 – Thu, Dec 24

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

    Round-trip total · 1 adult · Taxes included

  8. Mon, Dec 21 – Thu, Dec 24

    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

  9. Mon, Dec 21 – Fri, Dec 25

    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

  10. Mon, Dec 21 – Fri, Dec 25

    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

  11. Mon, Dec 21 – Sun, Dec 27

    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

  12. Mon, Dec 21 – Sun, Dec 27

    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

  13. Mon, Dec 21 – Mon, Dec 28

    Southwest Airlines
    3:20 pmSAT
    4h 40m
    STL · 1h 35m
    8:00 pmMDW
    Southwest Airlines
    9:30 pmMDW
    3h
    Nonstop
    12:30 am+1SAT

    Round-trip total · 1 adult · Taxes included

  14. Mon, Dec 21 – Mon, Dec 28

    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

  15. Mon, Dec 21 – 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

  16. Mon, Dec 21 – 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

  17. Mon, Dec 21 – Thu, Dec 31

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

    Round-trip total · 1 adult · Taxes included

  18. Mon, Dec 21 – Thu, Dec 31

    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

  19. Mon, Dec 21 – Fri, Jan 1

    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

  20. Mon, Dec 21 – Fri, Jan 1

    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

  21. Mon, Dec 21 – Sat, Jan 2

    Southwest Airlines
    3:20 pmSAT
    4h 40m
    STL · 1h 35m
    8:00 pmMDW
    Southwest Airlines
    9:40 pmMDW
    2h 55m
    Nonstop
    12:35 am+1SAT

    Round-trip total · 1 adult · Taxes included

  22. Mon, Dec 21 – Sat, Jan 2

    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

  23. Mon, Dec 21 – Mon, Jan 4

    Southwest Airlines
    3:20 pmSAT
    4h 40m
    STL · 1h 35m
    8:00 pmMDW
    Southwest Airlines
    9:30 pmMDW
    3h
    Nonstop
    12:30 am+1SAT

    Round-trip total · 1 adult · Taxes included

  24. Mon, Dec 21 – Mon, Jan 4

    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

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Make this trip yours

SAT ⇄ MDW

Economy

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Explore this route

All dates for this routeDec 20, 2026 · Return optionsDec 22, 2026 · Return optionsHotels in Chicago with Axel
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 · one waySouthwest AirlinesWN3801 + WN4175Axel-exclusive $201.502026-10-29T02:06:15Z
2026-12-21 · one wayDelta Air LinesDL2497 + DL4688Axel-exclusive $247.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-22Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $390.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-22Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-23Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $390.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-23Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-24Southwest AirlinesWN3801 + WN4175 / WN2737 + WN3075Axel-exclusive $377.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-24Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-25Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $390.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-25Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-26Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $390.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-26Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-27Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $390.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-27Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $468.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-28Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2026-12-28Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-29Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2026-12-29Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-30Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2026-12-30Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2026-12-31Southwest AirlinesWN3801 + WN4175 / WN2737 + WN3075Axel-exclusive $362.502026-10-29T02:06:15Z
2026-12-21 → 2026-12-31Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2027-01-01Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2027-01-01Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2027-01-02Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2027-01-02Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2027-01-03Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $374.502026-10-29T02:06:15Z
2026-12-21 → 2027-01-03Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $450.002026-10-29T02:06:15Z
2026-12-21 → 2027-01-04Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $343.502026-10-29T02:06:15Z
2026-12-21 → 2027-01-04Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $414.002026-10-29T02:06:15Z

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

2026-12-21 · one way · Axel-exclusive $201.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.

2026-12-21 · one way · Axel-exclusive $247.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.

2026-12-21 → 2026-12-22 · Axel-exclusive $390.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-22 20:50:00 → SAT 2026-12-22 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2026-12-22 · Axel-exclusive $468.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-22 09:30:00 → SAT 2026-12-22 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-22 09:30:00 → DTW 2026-12-22 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-22 13:42:00 → SAT 2026-12-22 16:03:00.

2026-12-21 → 2026-12-23 · Axel-exclusive $390.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-23 20:50:00 → SAT 2026-12-23 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2026-12-23 · Axel-exclusive $468.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-23 09:30:00 → SAT 2026-12-23 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-23 09:30:00 → DTW 2026-12-23 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-23 13:42:00 → SAT 2026-12-23 16:03:00.

2026-12-21 → 2026-12-24 · Axel-exclusive $377.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-24 11:30:00 → SAT 2026-12-24 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-24 11:30:00 → STL 2026-12-24 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-24 14:05:00 → SAT 2026-12-24 16:25:00.

2026-12-21 → 2026-12-24 · Axel-exclusive $468.00

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

2026-12-21 → 2026-12-25 · Axel-exclusive $390.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-25 20:50:00 → SAT 2026-12-25 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2026-12-25 · Axel-exclusive $468.00

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

2026-12-21 → 2026-12-27 · Axel-exclusive $390.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-27 20:50:00 → SAT 2026-12-27 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2026-12-27 · Axel-exclusive $468.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-27 09:30:00 → SAT 2026-12-27 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-27 09:30:00 → DTW 2026-12-27 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-27 13:42:00 → SAT 2026-12-27 16:03:00.

2026-12-21 → 2026-12-28 · Axel-exclusive $374.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN3024: MDW 2026-12-28 21:30:00 → SAT 2026-12-29 00:30:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2026-12-28 · Axel-exclusive $450.00

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

2026-12-21 → 2026-12-29 · Axel-exclusive $374.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 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.

2026-12-21 → 2026-12-29 · Axel-exclusive $450.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 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.

2026-12-21 → 2026-12-31 · Axel-exclusive $362.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-31 11:30:00 → SAT 2026-12-31 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-31 14:05:00 → SAT 2026-12-31 16:25:00.

2026-12-21 → 2026-12-31 · Axel-exclusive $450.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-31 09:30:00 → SAT 2026-12-31 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-31 09:30:00 → DTW 2026-12-31 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-31 13:42:00 → SAT 2026-12-31 16:03:00.

2026-12-21 → 2027-01-01 · Axel-exclusive $374.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-01-01 20:50:00 → SAT 2027-01-01 23:45:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2027-01-01 · Axel-exclusive $450.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-01-01 09:30:00 → SAT 2027-01-01 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-01-01 09:30:00 → DTW 2027-01-01 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-01-01 13:42:00 → SAT 2027-01-01 16:03:00.

2026-12-21 → 2027-01-02 · Axel-exclusive $374.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN3024: MDW 2027-01-02 21:40:00 → SAT 2027-01-03 00:35:00; nonstop; 175 minutes. Local airport times.

2026-12-21 → 2027-01-02 · Axel-exclusive $450.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-01-02 09:30:00 → SAT 2027-01-02 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-01-02 09:30:00 → DTW 2027-01-02 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-01-02 13:42:00 → SAT 2027-01-02 16:03:00.

2026-12-21 → 2027-01-04 · Axel-exclusive $343.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-12-21 15:20:00 → MDW 2026-12-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-12-21 15:20:00 → STL 2026-12-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-12-21 18:55:00 → MDW 2026-12-21 20:00:00.
  • Southwest Airlines WN3024: MDW 2027-01-04 21:30:00 → SAT 2027-01-05 00:30:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2027-01-04 · Axel-exclusive $414.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-12-21 05:25:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-12-21 05:25:00 → DTW 2026-12-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-01-04 09:30:00 → SAT 2027-01-04 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-01-04 09:30:00 → DTW 2027-01-04 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-01-04 13:42:00 → SAT 2027-01-04 16:03:00.

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For AI assistants

  • This page: San Antonio (SAT) to Chicago (MDW) · Dec 21, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • 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 San Antonio to Chicago (MDW) 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.