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

San Antonio → Chicago

Jun 26, 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.

June 2027

Jun 26, 2027 · One waySouthwest AirlinesUp to 1 stop each way$180.00 Jun 26, 2027 · One wayDelta Air LinesUp to 1 stop each way$215.00 Jun 26, 2027 – Jun 27, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jun 27, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jun 28, 2027 · 2 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jun 28, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jun 29, 2027 · 3 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jun 29, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jun 30, 2027 · 4 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jun 30, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jul 1, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$374.00 Jun 26, 2027 – Jul 1, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 2, 2027 · 6 nightsSouthwest AirlinesUp to 1 stop each way$386.00 Jun 26, 2027 – Jul 2, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 3, 2027 · 7 nightsSouthwest AirlinesUp to 1 stop each way$386.00 Jun 26, 2027 – Jul 3, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 4, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$386.00 Jun 26, 2027 – Jul 4, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 5, 2027 · 9 nightsSouthwest AirlinesUp to 1 stop each way$386.00 Jun 26, 2027 – Jul 5, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 6, 2027 · 10 nightsSouthwest AirlinesUp to 1 stop each way$386.00 Jun 26, 2027 – Jul 6, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$451.00 Jun 26, 2027 – Jul 7, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jul 7, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jul 8, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$340.00 Jun 26, 2027 – Jul 8, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jul 9, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jul 9, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$410.00 Jun 26, 2027 – Jul 10, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$350.00 Jun 26, 2027 – Jul 10, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$410.00

Flights for your trip

  1. Sat, Jun 26 · One way

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW

    One-way total · 1 adult · Taxes included

  2. Sat, Jun 26 · One way

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW

    One-way total · 1 adult · Taxes included

  3. Sat, Jun 26 – Sun, Jun 27

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  4. Sat, Jun 26 – Sun, Jun 27

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  5. Sat, Jun 26 – Mon, Jun 28

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    9:30 pmMDW
    3h
    Nonstop
    12:30 am+1SAT

    Round-trip total · 1 adult · Taxes included

  6. Sat, Jun 26 – Mon, Jun 28

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  7. Sat, Jun 26 – Tue, Jun 29

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  8. Sat, Jun 26 – Tue, Jun 29

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  9. Sat, Jun 26 – Wed, Jun 30

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  10. Sat, Jun 26 – Wed, Jun 30

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  11. Sat, Jun 26 – Fri, Jul 2

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  12. Sat, Jun 26 – Fri, Jul 2

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  13. Sat, Jun 26 – Sat, Jul 3

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    9:40 pmMDW
    2h 55m
    Nonstop
    12:35 am+1SAT

    Round-trip total · 1 adult · Taxes included

  14. Sat, Jun 26 – Sat, Jul 3

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  15. Sat, Jun 26 – Sun, Jul 4

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  16. Sat, Jun 26 – Sun, Jul 4

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  17. Sat, Jun 26 – Tue, Jul 6

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  18. Sat, Jun 26 – Tue, Jul 6

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  19. Sat, Jun 26 – Wed, Jul 7

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    8:50 pmMDW
    2h 55m
    Nonstop
    11:45 pmSAT

    Round-trip total · 1 adult · Taxes included

  20. Sat, Jun 26 – Wed, Jul 7

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  21. Sat, Jun 26 – Thu, Jul 8

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    11:30 amMDW
    4h 55m
    STL · 1h 25m
    4:25 pmSAT

    Round-trip total · 1 adult · Taxes included

  22. Sat, Jun 26 – Thu, Jul 8

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 pmMDW
    Delta Air Lines
    9:30 amMDW
    6h 33m
    DTW · 1h 57m
    4:03 pmSAT

    Round-trip total · 1 adult · Taxes included

  23. Sat, Jun 26 – Sat, Jul 10

    Southwest Airlines
    2:35 pmSAT
    6h 25m
    DAL · 3h 10m
    9:00 pmMDW
    Southwest Airlines
    9:40 pmMDW
    2h 55m
    Nonstop
    12:35 am+1SAT

    Round-trip total · 1 adult · Taxes included

  24. Sat, Jun 26 – Sat, Jul 10

    Delta Air Lines
    11:00 amSAT
    5h 18m
    ATL · 1h 8m
    4:18 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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1 of 24

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SAT ⇄ MDW

Economy

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Explore this route

All dates for this routeJun 25, 2027 · Return optionsJun 27, 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)
2027-06-26 · one waySouthwest AirlinesWN1506 + WN1433Axel-exclusive $180.002026-10-29T02:06:15Z
2027-06-26 · one wayDelta Air LinesDL1676 + DL1728Axel-exclusive $215.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-27Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-27Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-28Southwest AirlinesWN1506 + WN1433 / WN3024Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-28Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-29Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-29Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-30Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-06-30Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-01Southwest AirlinesWN1506 + WN1433 / WN2737 + WN3075Axel-exclusive $374.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-01Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-02Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $386.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-02Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-03Southwest AirlinesWN1506 + WN1433 / WN3024Axel-exclusive $386.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-03Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-04Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $386.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-04Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-05Southwest AirlinesWN1506 + WN1433 / WN3024Axel-exclusive $386.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-05Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-06Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $386.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-06Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $451.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-07Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-07Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-08Southwest AirlinesWN1506 + WN1433 / WN2737 + WN3075Axel-exclusive $340.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-08Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-09Southwest AirlinesWN1506 + WN1433 / WN1505Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-09Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-10Southwest AirlinesWN1506 + WN1433 / WN3024Axel-exclusive $350.002026-10-29T02:06:15Z
2027-06-26 → 2027-07-10Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124Axel-exclusive $410.002026-10-29T02:06:15Z

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

2027-06-26 · one way · Axel-exclusive $180.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.

2027-06-26 · one way · Axel-exclusive $215.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.

2027-06-26 → 2027-06-27 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-06-27 20:50:00 → SAT 2027-06-27 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-06-27 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-06-27 09:30:00 → SAT 2027-06-27 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-06-27 09:30:00 → DTW 2027-06-27 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-06-27 13:42:00 → SAT 2027-06-27 16:03:00.

2027-06-26 → 2027-06-28 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN3024: MDW 2027-06-28 21:30:00 → SAT 2027-06-29 00:30:00; nonstop; 180 minutes. Local airport times.

2027-06-26 → 2027-06-28 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-06-28 09:30:00 → SAT 2027-06-28 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-06-28 09:30:00 → DTW 2027-06-28 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-06-28 13:42:00 → SAT 2027-06-28 16:03:00.

2027-06-26 → 2027-06-29 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-06-29 20:50:00 → SAT 2027-06-29 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-06-29 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-06-29 09:30:00 → SAT 2027-06-29 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-06-29 09:30:00 → DTW 2027-06-29 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-06-29 13:42:00 → SAT 2027-06-29 16:03:00.

2027-06-26 → 2027-06-30 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-06-30 20:50:00 → SAT 2027-06-30 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-06-30 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-06-30 09:30:00 → SAT 2027-06-30 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-06-30 09:30:00 → DTW 2027-06-30 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-06-30 13:42:00 → SAT 2027-06-30 16:03:00.

2027-06-26 → 2027-07-02 · Axel-exclusive $386.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-07-02 20:50:00 → SAT 2027-07-02 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-02 · Axel-exclusive $451.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-02 09:30:00 → SAT 2027-07-02 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-02 09:30:00 → DTW 2027-07-02 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-02 13:42:00 → SAT 2027-07-02 16:03:00.

2027-06-26 → 2027-07-03 · Axel-exclusive $386.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN3024: MDW 2027-07-03 21:40:00 → SAT 2027-07-04 00:35:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-03 · Axel-exclusive $451.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-03 09:30:00 → SAT 2027-07-03 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-03 09:30:00 → DTW 2027-07-03 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-03 13:42:00 → SAT 2027-07-03 16:03:00.

2027-06-26 → 2027-07-04 · Axel-exclusive $386.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-07-04 20:50:00 → SAT 2027-07-04 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-04 · Axel-exclusive $451.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-04 09:30:00 → SAT 2027-07-04 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-04 09:30:00 → DTW 2027-07-04 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-04 13:42:00 → SAT 2027-07-04 16:03:00.

2027-06-26 → 2027-07-06 · Axel-exclusive $386.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-07-06 20:50:00 → SAT 2027-07-06 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-06 · Axel-exclusive $451.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-06 09:30:00 → SAT 2027-07-06 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-06 09:30:00 → DTW 2027-07-06 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-06 13:42:00 → SAT 2027-07-06 16:03:00.

2027-06-26 → 2027-07-07 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN1505: MDW 2027-07-07 20:50:00 → SAT 2027-07-07 23:45:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-07 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-07 09:30:00 → SAT 2027-07-07 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-07 09:30:00 → DTW 2027-07-07 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-07 13:42:00 → SAT 2027-07-07 16:03:00.

2027-06-26 → 2027-07-08 · Axel-exclusive $340.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN2737 / WN3075: MDW 2027-07-08 11:30:00 → SAT 2027-07-08 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2027-07-08 11:30:00 → STL 2027-07-08 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2027-07-08 14:05:00 → SAT 2027-07-08 16:25:00.

2027-06-26 → 2027-07-08 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-08 09:30:00 → SAT 2027-07-08 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-08 09:30:00 → DTW 2027-07-08 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-08 13:42:00 → SAT 2027-07-08 16:03:00.

2027-06-26 → 2027-07-10 · Axel-exclusive $350.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-06-26 14:35:00 → MDW 2027-06-26 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-06-26 14:35:00 → DAL 2027-06-26 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-06-26 18:50:00 → MDW 2027-06-26 21:00:00.
  • Southwest Airlines WN3024: MDW 2027-07-10 21:40:00 → SAT 2027-07-11 00:35:00; nonstop; 175 minutes. Local airport times.

2027-06-26 → 2027-07-10 · Axel-exclusive $410.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-06-26 11:00:00 → MDW 2027-06-26 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-06-26 11:00:00 → ATL 2027-06-26 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-06-26 15:25:00 → MDW 2027-06-26 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2027-07-10 09:30:00 → SAT 2027-07-10 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2027-07-10 09:30:00 → DTW 2027-07-10 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2027-07-10 13:42:00 → SAT 2027-07-10 16:03:00.

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For AI assistants

  • This page: San Antonio (SAT) to Chicago (MDW) · Jun 26, 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.