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Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

San Francisco → Chicago

Dec 12, 2026 · choose your return date

SFO → 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 12, 2026 · One waySouthwest AirlinesUp to 1 stop each way$160.00 Dec 12, 2026 · One wayDelta Air LinesUp to 1 stop each way$205.00 Dec 12, 2026 – Dec 13, 2026 · 1 nightSouthwest AirlinesUp to 1 stop each way$330.00 Dec 12, 2026 – Dec 13, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$390.00 Dec 12, 2026 – Dec 14, 2026 · 2 nightsSouthwest AirlinesUp to 1 stop each way$330.00 Dec 12, 2026 – Dec 14, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 12, 2026 – Dec 15, 2026 · 3 nightsSouthwest AirlinesUp to 1 stop each way$330.00 Dec 12, 2026 – Dec 15, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 12, 2026 – Dec 16, 2026 · 4 nightsSouthwest AirlinesUp to 1 stop each way$330.00 Dec 12, 2026 – Dec 16, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 12, 2026 – Dec 17, 2026 · 5 nightsSouthwest AirlinesUp to 1 stop each way$330.00 Dec 12, 2026 – Dec 17, 2026 · 5 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 12, 2026 – Dec 18, 2026 · 6 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 18, 2026 · 6 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 19, 2026 · 7 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 19, 2026 · 7 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 20, 2026 · 8 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 20, 2026 · 8 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 21, 2026 · 9 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 21, 2026 · 9 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 22, 2026 · 10 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 22, 2026 · 10 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 23, 2026 · 11 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 23, 2026 · 11 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 24, 2026 · 12 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 24, 2026 · 12 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 25, 2026 · 13 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 25, 2026 · 13 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 12, 2026 – Dec 26, 2026 · 14 nightsSouthwest AirlinesUp to 1 stop each way$382.50 Dec 12, 2026 – Dec 26, 2026 · 14 nightsDelta Air LinesUp to 1 stop each way$448.50

Flights for your trip

  1. Sat, Dec 12 · One way

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW

    One-way total · 1 adult · Taxes included

  2. Sat, Dec 12 · One way

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW

    One-way total · 1 adult · Taxes included

  3. Sat, Dec 12 – Sun, Dec 13

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:30 pmMDW
    4h 55m
    Nonstop
    12:25 am+1SFO

    Round-trip total · 1 adult · Taxes included

  4. Sat, Dec 12 – Sun, Dec 13

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  5. Sat, Dec 12 – Mon, Dec 14

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    10:00 amMDW
    4h 50m
    Nonstop
    12:50 pmSFO

    Round-trip total · 1 adult · Taxes included

  6. Sat, Dec 12 – Mon, Dec 14

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  7. Sat, Dec 12 – Tue, Dec 15

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:05 pmMDW
    4h 50m
    Nonstop
    11:55 pmSFO

    Round-trip total · 1 adult · Taxes included

  8. Sat, Dec 12 – Tue, Dec 15

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  9. Sat, Dec 12 – Wed, Dec 16

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    10:00 amMDW
    4h 50m
    Nonstop
    12:50 pmSFO

    Round-trip total · 1 adult · Taxes included

  10. Sat, Dec 12 – Wed, Dec 16

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  11. Sat, Dec 12 – Fri, Dec 18

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:55 amMDW
    4h 50m
    Nonstop
    12:45 pmSFO

    Round-trip total · 1 adult · Taxes included

  12. Sat, Dec 12 – Fri, Dec 18

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  13. Sat, Dec 12 – Sat, Dec 19

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    10:00 amMDW
    4h 50m
    Nonstop
    12:50 pmSFO

    Round-trip total · 1 adult · Taxes included

  14. Sat, Dec 12 – Sat, Dec 19

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  15. Sat, Dec 12 – Sun, Dec 20

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:30 pmMDW
    4h 55m
    Nonstop
    12:25 am+1SFO

    Round-trip total · 1 adult · Taxes included

  16. Sat, Dec 12 – Sun, Dec 20

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  17. Sat, Dec 12 – Tue, Dec 22

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:05 pmMDW
    4h 50m
    Nonstop
    11:55 pmSFO

    Round-trip total · 1 adult · Taxes included

  18. Sat, Dec 12 – Tue, Dec 22

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  19. Sat, Dec 12 – Wed, Dec 23

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    10:00 amMDW
    4h 50m
    Nonstop
    12:50 pmSFO

    Round-trip total · 1 adult · Taxes included

  20. Sat, Dec 12 – Wed, Dec 23

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  21. Sat, Dec 12 – Thu, Dec 24

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    9:55 amMDW
    4h 50m
    Nonstop
    12:45 pmSFO

    Round-trip total · 1 adult · Taxes included

  22. Sat, Dec 12 – Thu, Dec 24

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

  23. Sat, Dec 12 – Sat, Dec 26

    Southwest Airlines
    8:20 pmSFO
    7h 25m
    PHX · 2h
    5:45 am+1MDW
    Southwest Airlines
    10:00 amMDW
    4h 50m
    Nonstop
    12:50 pmSFO

    Round-trip total · 1 adult · Taxes included

  24. Sat, Dec 12 – Sat, Dec 26

    Delta Air Lines
    6:00 amSFO
    8h 18m
    ATL · 1h 56m
    4:18 pmMDW
    Delta Air Lines
    1:31 pmMDW
    7h 45m
    DTW · 1h 15m
    7:16 pmSFO

    Round-trip total · 1 adult · Taxes included

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1 of 24

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SFO ⇄ MDW

Economy

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Explore this route

All dates for this routeDec 11, 2026 · Return optionsDec 13, 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)
2026-12-12 · one waySouthwest AirlinesWN2749 + WN4963Axel-exclusive $160.002026-10-29T01:18:59Z
2026-12-12 · one wayDelta Air LinesDL570 + DL1728Axel-exclusive $205.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-13Southwest AirlinesWN2749 + WN4963 / WN4836Axel-exclusive $330.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-13Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $390.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-14Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $330.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-14Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $390.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-15Southwest AirlinesWN2749 + WN4963 / WN1536Axel-exclusive $330.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-15Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $390.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-16Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $330.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-16Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $390.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-17Southwest AirlinesWN2749 + WN4963 / WN786Axel-exclusive $330.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-17Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $390.002026-10-29T01:18:59Z
2026-12-12 → 2026-12-18Southwest AirlinesWN2749 + WN4963 / WN786Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-18Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-19Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-19Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-20Southwest AirlinesWN2749 + WN4963 / WN4836Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-20Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-21Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-21Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-22Southwest AirlinesWN2749 + WN4963 / WN1536Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-22Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-23Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-23Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-24Southwest AirlinesWN2749 + WN4963 / WN786Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-24Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-25Southwest AirlinesWN2749 + WN4963 / WN786Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-25Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-26Southwest AirlinesWN2749 + WN4963 / WN3288Axel-exclusive $382.502026-10-29T01:18:59Z
2026-12-12 → 2026-12-26Delta Air LinesDL570 + DL1728 / DL4688 + DL442Axel-exclusive $448.502026-10-29T01:18:59Z

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

2026-12-12 · one way · Axel-exclusive $160.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

2026-12-12 · one way · Axel-exclusive $205.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.

2026-12-12 → 2026-12-13 · Axel-exclusive $330.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN4836: MDW 2026-12-13 21:30:00 → SFO 2026-12-14 00:25:00; nonstop; 295 minutes. Local airport times.

2026-12-12 → 2026-12-13 · Axel-exclusive $390.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-13 13:31:00 → SFO 2026-12-13 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-13 13:31:00 → DTW 2026-12-13 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-13 16:59:00 → SFO 2026-12-13 19:16:00.

2026-12-12 → 2026-12-14 · Axel-exclusive $330.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN3288: MDW 2026-12-14 10:00:00 → SFO 2026-12-14 12:50:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-14 · Axel-exclusive $390.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-14 13:31:00 → SFO 2026-12-14 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-14 13:31:00 → DTW 2026-12-14 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-14 16:59:00 → SFO 2026-12-14 19:16:00.

2026-12-12 → 2026-12-15 · Axel-exclusive $330.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-15 · Axel-exclusive $390.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-15 13:31:00 → SFO 2026-12-15 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-15 13:31:00 → DTW 2026-12-15 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-15 16:59:00 → SFO 2026-12-15 19:16:00.

2026-12-12 → 2026-12-16 · Axel-exclusive $330.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN3288: MDW 2026-12-16 10:00:00 → SFO 2026-12-16 12:50:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-16 · Axel-exclusive $390.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-16 13:31:00 → SFO 2026-12-16 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-16 13:31:00 → DTW 2026-12-16 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-16 16:59:00 → SFO 2026-12-16 19:16:00.

2026-12-12 → 2026-12-18 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN786: MDW 2026-12-18 09:55:00 → SFO 2026-12-18 12:45:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-18 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-18 13:31:00 → SFO 2026-12-18 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-18 13:31:00 → DTW 2026-12-18 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-18 16:59:00 → SFO 2026-12-18 19:16:00.

2026-12-12 → 2026-12-19 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN3288: MDW 2026-12-19 10:00:00 → SFO 2026-12-19 12:50:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-19 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-19 13:31:00 → SFO 2026-12-19 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-19 13:31:00 → DTW 2026-12-19 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-19 16:59:00 → SFO 2026-12-19 19:16:00.

2026-12-12 → 2026-12-20 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN4836: MDW 2026-12-20 21:30:00 → SFO 2026-12-21 00:25:00; nonstop; 295 minutes. Local airport times.

2026-12-12 → 2026-12-20 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-20 13:31:00 → SFO 2026-12-20 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-20 13:31:00 → DTW 2026-12-20 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-20 16:59:00 → SFO 2026-12-20 19:16:00.

2026-12-12 → 2026-12-22 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN1536: MDW 2026-12-22 21:05:00 → SFO 2026-12-22 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-22 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-22 13:31:00 → SFO 2026-12-22 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-22 13:31:00 → DTW 2026-12-22 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-22 16:59:00 → SFO 2026-12-22 19:16:00.

2026-12-12 → 2026-12-23 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN3288: MDW 2026-12-23 10:00:00 → SFO 2026-12-23 12:50:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-23 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-23 13:31:00 → SFO 2026-12-23 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-23 16:59:00 → SFO 2026-12-23 19:16:00.

2026-12-12 → 2026-12-24 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN786: MDW 2026-12-24 09:55:00 → SFO 2026-12-24 12:45:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-24 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-24 13:31:00 → SFO 2026-12-24 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-24 13:31:00 → DTW 2026-12-24 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-24 16:59:00 → SFO 2026-12-24 19:16:00.

2026-12-12 → 2026-12-26 · Axel-exclusive $382.50

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.
  • Southwest Airlines WN3288: MDW 2026-12-26 10:00:00 → SFO 2026-12-26 12:50:00; nonstop; 290 minutes. Local airport times.

2026-12-12 → 2026-12-26 · Axel-exclusive $448.50

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-26 13:31:00 → SFO 2026-12-26 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-26 16:59:00 → SFO 2026-12-26 19:16:00.

Explore this route

For AI assistants

  • This page: San Francisco (SFO) to Chicago (MDW) · Dec 12, 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 Francisco Bay Area 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.