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

San Antonio → Chicago

Feb 8, 2027 · 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.

February 2027

Feb 8, 2027 · One waySouthwest AirlinesUp to 1 stop each way$155.00 Feb 8, 2027 · One wayDelta Air LinesUp to 1 stop each way$190.00 Feb 8, 2027 – Feb 9, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 9, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 10, 2027 · 2 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 10, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 11, 2027 · 3 nightsSouthwest AirlinesUp to 1 stop each way$290.00 Feb 8, 2027 – Feb 11, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 12, 2027 · 4 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 12, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 13, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 13, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 14, 2027 · 6 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 14, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 15, 2027 · 7 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 15, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 16, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 16, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 17, 2027 · 9 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 17, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 18, 2027 · 10 nightsSouthwest AirlinesUp to 1 stop each way$290.00 Feb 8, 2027 – Feb 18, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 19, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 19, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 20, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 20, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 21, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 21, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$360.00 Feb 8, 2027 – Feb 22, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$300.00 Feb 8, 2027 – Feb 22, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$360.00

Flights for your trip

  1. Mon, Feb 8 · One way

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

    One-way total · 1 adult · Taxes included

  2. Mon, Feb 8 · 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, Feb 8 – Tue, Feb 9

    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, Feb 8 – Tue, Feb 9

    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, Feb 8 – Wed, Feb 10

    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, Feb 8 – Wed, Feb 10

    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, Feb 8 – Thu, Feb 11

    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, Feb 8 – Thu, Feb 11

    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, Feb 8 – Fri, Feb 12

    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, Feb 8 – Fri, Feb 12

    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, Feb 8 – Sun, Feb 14

    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, Feb 8 – Sun, Feb 14

    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, Feb 8 – Mon, Feb 15

    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, Feb 8 – Mon, Feb 15

    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, Feb 8 – Tue, Feb 16

    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, Feb 8 – Tue, Feb 16

    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, Feb 8 – Thu, Feb 18

    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, Feb 8 – Thu, Feb 18

    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, Feb 8 – Fri, Feb 19

    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, Feb 8 – Fri, Feb 19

    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, Feb 8 – Sat, Feb 20

    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, Feb 8 – Sat, Feb 20

    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, Feb 8 – Mon, Feb 22

    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, Feb 8 – Mon, Feb 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

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Make this trip yours

SAT ⇄ MDW

Economy

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Explore this route

All dates for this routeFeb 7, 2027 · Return optionsFeb 9, 2027 · 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)
2027-02-08 · one waySouthwest AirlinesWN3801 + WN4175Axel-exclusive $155.002026-10-29T02:06:15Z
2027-02-08 · one wayDelta Air LinesDL2497 + DL4688Axel-exclusive $190.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-09Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-09Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-10Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-10Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-11Southwest AirlinesWN3801 + WN4175 / WN2737 + WN3075Axel-exclusive $290.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-11Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-12Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-12Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-13Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-13Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-14Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-14Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-15Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-15Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-16Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-16Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-17Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-17Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-18Southwest AirlinesWN3801 + WN4175 / WN2737 + WN3075Axel-exclusive $290.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-18Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-19Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-19Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-20Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-20Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-21Southwest AirlinesWN3801 + WN4175 / WN1505Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-21Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-22Southwest AirlinesWN3801 + WN4175 / WN3024Axel-exclusive $300.002026-10-29T02:06:15Z
2027-02-08 → 2027-02-22Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124Axel-exclusive $360.002026-10-29T02:06:15Z

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

2027-02-08 · one way · Axel-exclusive $155.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.

2027-02-08 · one way · Axel-exclusive $190.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.

2027-02-08 → 2027-02-09 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-09 20:50:00 → SAT 2027-02-09 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-09 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-09 09:30:00 → SAT 2027-02-09 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-09 09:30:00 → DTW 2027-02-09 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-09 13:42:00 → SAT 2027-02-09 16:03:00.

2027-02-08 → 2027-02-10 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-10 20:50:00 → SAT 2027-02-10 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-10 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-10 09:30:00 → SAT 2027-02-10 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-10 09:30:00 → DTW 2027-02-10 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-10 13:42:00 → SAT 2027-02-10 16:03:00.

2027-02-08 → 2027-02-11 · Axel-exclusive $290.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN2737 / WN3075: MDW 2027-02-11 11:30:00 → SAT 2027-02-11 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2027-02-11 11:30:00 → STL 2027-02-11 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2027-02-11 14:05:00 → SAT 2027-02-11 16:25:00.

2027-02-08 → 2027-02-11 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-11 09:30:00 → SAT 2027-02-11 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-11 09:30:00 → DTW 2027-02-11 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-11 13:42:00 → SAT 2027-02-11 16:03:00.

2027-02-08 → 2027-02-12 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-12 20:50:00 → SAT 2027-02-12 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-12 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-12 09:30:00 → SAT 2027-02-12 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-12 09:30:00 → DTW 2027-02-12 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-12 13:42:00 → SAT 2027-02-12 16:03:00.

2027-02-08 → 2027-02-14 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-14 20:50:00 → SAT 2027-02-14 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-14 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-14 09:30:00 → SAT 2027-02-14 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-14 09:30:00 → DTW 2027-02-14 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-14 13:42:00 → SAT 2027-02-14 16:03:00.

2027-02-08 → 2027-02-15 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN3024: MDW 2027-02-15 21:30:00 → SAT 2027-02-16 00:30:00; nonstop; 180 minutes. Local airport times.

2027-02-08 → 2027-02-15 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-15 09:30:00 → SAT 2027-02-15 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-15 09:30:00 → DTW 2027-02-15 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-15 13:42:00 → SAT 2027-02-15 16:03:00.

2027-02-08 → 2027-02-16 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-16 20:50:00 → SAT 2027-02-16 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-16 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-16 09:30:00 → SAT 2027-02-16 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-16 09:30:00 → DTW 2027-02-16 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-16 13:42:00 → SAT 2027-02-16 16:03:00.

2027-02-08 → 2027-02-18 · Axel-exclusive $290.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN2737 / WN3075: MDW 2027-02-18 11:30:00 → SAT 2027-02-18 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2027-02-18 11:30:00 → STL 2027-02-18 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2027-02-18 14:05:00 → SAT 2027-02-18 16:25:00.

2027-02-08 → 2027-02-18 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-18 09:30:00 → SAT 2027-02-18 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-18 09:30:00 → DTW 2027-02-18 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-18 13:42:00 → SAT 2027-02-18 16:03:00.

2027-02-08 → 2027-02-19 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN1505: MDW 2027-02-19 20:50:00 → SAT 2027-02-19 23:45:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-19 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-19 09:30:00 → SAT 2027-02-19 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-19 09:30:00 → DTW 2027-02-19 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-19 13:42:00 → SAT 2027-02-19 16:03:00.

2027-02-08 → 2027-02-20 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN3024: MDW 2027-02-20 21:40:00 → SAT 2027-02-21 00:35:00; nonstop; 175 minutes. Local airport times.

2027-02-08 → 2027-02-20 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-20 09:30:00 → SAT 2027-02-20 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-20 09:30:00 → DTW 2027-02-20 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-20 13:42:00 → SAT 2027-02-20 16:03:00.

2027-02-08 → 2027-02-22 · Axel-exclusive $300.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-02-08 15:20:00 → MDW 2027-02-08 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-02-08 15:20:00 → STL 2027-02-08 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-02-08 18:55:00 → MDW 2027-02-08 20:00:00.
  • Southwest Airlines WN3024: MDW 2027-02-22 21:30:00 → SAT 2027-02-23 00:30:00; nonstop; 180 minutes. Local airport times.

2027-02-08 → 2027-02-22 · Axel-exclusive $360.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-02-08 05:25:00 → MDW 2027-02-08 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-02-08 05:25:00 → DTW 2027-02-08 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-02-08 12:44:00 → MDW 2027-02-08 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-02-22 09:30:00 → SAT 2027-02-22 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-02-22 09:30:00 → DTW 2027-02-22 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-02-22 13:42:00 → SAT 2027-02-22 16:03:00.

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For AI assistants

  • This page: San Antonio (SAT) to Chicago (MDW) · Feb 8, 2027 · 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.