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Chicago → San Francisco

Dec 8, 2026 · return Dec 11, 2026

MDW → SFO1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Tue, Dec 8 – Fri, Dec 11

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Fri, Dec 11

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

Tue, Dec 8 – Fri, Dec 11

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Fri, Dec 11

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Fri, Dec 11

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Fri, Dec 11

Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 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 routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
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)
2026-12-08 → 2026-12-11Southwest AirlinesWN142 + WN2440 / WN3847 + WN2515$300.002026-10-29T01:29:13Z
2026-12-08 → 2026-12-11Delta Air LinesDL4688 + DL442 / DL570 + DL1728$350.002026-10-29T01:29:13Z
2026-12-08 → 2026-12-11Southwest AirlinesWN725 + WN4254 / WN3847 + WN2515$300.002026-10-29T01:29:13Z
2026-12-08 → 2026-12-11Southwest AirlinesWN4606 + WN1817 / WN3847 + WN2515$300.002026-10-29T01:29:13Z
2026-12-08 → 2026-12-11Southwest AirlinesWN2998 + WN1448 / WN3847 + WN2515$300.002026-10-29T01:29:13Z
2026-12-08 → 2026-12-11Southwest AirlinesWN1536 / WN3847 + WN2515$315.002026-10-29T01:29:13Z

2026-12-08 → 2026-12-11 · $300.00

  • Southwest Airlines WN142 / WN2440: MDW 2026-12-08 10:00:00 → SFO 2026-12-08 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-12-08 10:00:00 → LAS 2026-12-08 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-12-08 14:00:00 → SFO 2026-12-08 15:45:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-11 08:20:00 → MDW 2026-12-11 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-11 08:20:00 → LAX 2026-12-11 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-11 11:15:00 → MDW 2026-12-11 17:15:00.

2026-12-08 → 2026-12-11 · $350.00

  • Delta Air Lines DL4688 / DL442: MDW 2026-12-08 13:31:00 → SFO 2026-12-08 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-08 13:31:00 → DTW 2026-12-08 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-08 16:59:00 → SFO 2026-12-08 19:16:00.
  • Delta Air Lines DL570 / DL1728: SFO 2026-12-11 06:00:00 → MDW 2026-12-11 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-11 06:00:00 → ATL 2026-12-11 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-11 15:25:00 → MDW 2026-12-11 16:18:00.

2026-12-08 → 2026-12-11 · $300.00

  • Southwest Airlines WN725 / WN4254: MDW 2026-12-08 09:55:00 → SFO 2026-12-08 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-12-08 09:55:00 → BNA 2026-12-08 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-12-08 12:50:00 → SFO 2026-12-08 15:50:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-11 08:20:00 → MDW 2026-12-11 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-11 08:20:00 → LAX 2026-12-11 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-11 11:15:00 → MDW 2026-12-11 17:15:00.

2026-12-08 → 2026-12-11 · $300.00

  • Southwest Airlines WN4606 / WN1817: MDW 2026-12-08 14:35:00 → SFO 2026-12-08 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-12-08 14:35:00 → DEN 2026-12-08 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-12-08 17:35:00 → SFO 2026-12-08 19:20:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-11 08:20:00 → MDW 2026-12-11 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-11 08:20:00 → LAX 2026-12-11 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-11 11:15:00 → MDW 2026-12-11 17:15:00.

2026-12-08 → 2026-12-11 · $300.00

  • Southwest Airlines WN2998 / WN1448: MDW 2026-12-08 18:05:00 → SFO 2026-12-08 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-12-08 18:05:00 → PHX 2026-12-08 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-12-08 22:45:00 → SFO 2026-12-08 23:55:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-11 08:20:00 → MDW 2026-12-11 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-11 08:20:00 → LAX 2026-12-11 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-11 11:15:00 → MDW 2026-12-11 17:15:00.

2026-12-08 → 2026-12-11 · $315.00

  • Southwest Airlines WN1536: MDW 2026-12-08 21:05:00 → SFO 2026-12-08 23:55:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-11 08:20:00 → MDW 2026-12-11 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-11 08:20:00 → LAX 2026-12-11 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-11 11:15:00 → MDW 2026-12-11 17:15:00.

More dates for this route