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Chicago → San Francisco

Dec 16, 2026 · return Dec 22, 2026

MDW → SFO1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 16 – Tue, Dec 22

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

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Tue, Dec 22

Southwest Airlines
1:55 pmMDW
8h 5m
AUS · 1h 25m
8:00 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SFO

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeOct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 13, 2026 → Nov 16, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 11, 2026 → Dec 14, 2026Dec 12, 2026 → Dec 19, 2026Dec 22, 2026 → Dec 27, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Dec 30, 2026 → Jan 2, 2027Jan 8, 2027 → Jan 11, 2027Jan 9, 2027 → Jan 16, 2027Jan 15, 2027 → Jan 18, 2027Jan 22, 2027 → Jan 25, 2027Jan 23, 2027 → Jan 30, 2027Feb 5, 2027 → Feb 8, 2027Feb 6, 2027 → Feb 13, 2027Feb 12, 2027 → Feb 15, 2027Mar 5, 2027 → Mar 8, 2027Mar 6, 2027 → Mar 13, 2027Mar 25, 2027 → Mar 29, 2027Apr 2, 2027 → Apr 5, 2027Apr 3, 2027 → Apr 10, 2027Apr 30, 2027 → May 3, 2027May 1, 2027 → May 8, 2027May 28, 2027 → May 31, 2027May 29, 2027 → Jun 5, 2027Jun 25, 2027 → Jun 28, 2027Jun 26, 2027 → Jul 3, 2027Jul 2, 2027 → Jul 6, 2027Jul 23, 2027 → Jul 26, 2027Jul 24, 2027 → Jul 31, 2027Aug 20, 2027 → Aug 23, 2027Aug 21, 2027 → Aug 28, 2027Sep 3, 2027 → Sep 6, 2027Sep 17, 2027 → Sep 20, 2027Oct 30, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-16 → 2026-12-22Southwest AirlinesWN3288 / WN2331$387.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Delta Air LinesDL4688 + DL442 / DL570 + DL1728$411.252026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN1536 / WN2331$387.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN725 + WN4254 / WN2331$372.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN142 + WN2440 / WN2331$372.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN4606 + WN1817 / WN2331$372.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN2998 + WN1448 / WN2331$372.752026-10-29T01:29:13Z
2026-12-16 → 2026-12-22Southwest AirlinesWN2891 + WN4893 / WN2331$372.752026-10-29T01:29:13Z

2026-12-16 → 2026-12-22 · $387.75

  • Southwest Airlines WN3288: MDW 2026-12-16 10:00:00 → SFO 2026-12-16 12:50:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $411.25

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

2026-12-16 → 2026-12-22 · $387.75

  • Southwest Airlines WN1536: MDW 2026-12-16 21:05:00 → SFO 2026-12-16 23:55:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $372.75

  • Southwest Airlines WN725 / WN4254: MDW 2026-12-16 09:55:00 → SFO 2026-12-16 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-12-16 09:55:00 → BNA 2026-12-16 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-12-16 12:50:00 → SFO 2026-12-16 15:50:00.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $372.75

  • Southwest Airlines WN142 / WN2440: MDW 2026-12-16 10:00:00 → SFO 2026-12-16 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-12-16 10:00:00 → LAS 2026-12-16 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-12-16 14:00:00 → SFO 2026-12-16 15:45:00.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $372.75

  • Southwest Airlines WN4606 / WN1817: MDW 2026-12-16 14:35:00 → SFO 2026-12-16 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-12-16 14:35:00 → DEN 2026-12-16 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-12-16 17:35:00 → SFO 2026-12-16 19:20:00.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $372.75

  • Southwest Airlines WN2998 / WN1448: MDW 2026-12-16 18:05:00 → SFO 2026-12-16 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-12-16 18:05:00 → PHX 2026-12-16 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-12-16 22:45:00 → SFO 2026-12-16 23:55:00.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

2026-12-16 → 2026-12-22 · $372.75

  • Southwest Airlines WN2891 / WN4893: MDW 2026-12-16 13:55:00 → SFO 2026-12-16 20:00:00; 1 stop(s) via AUS; 485 minutes. Local airport times.
    • WN2891: MDW 2026-12-16 13:55:00 → AUS 2026-12-16 16:35:00; layover at AUS: 85 minutes.
    • WN4893: AUS 2026-12-16 18:00:00 → SFO 2026-12-16 20:00:00.
  • Southwest Airlines WN2331: SFO 2026-12-22 06:00:00 → MDW 2026-12-22 12:15:00; nonstop; 255 minutes. Local airport times.

More dates for this route