Chicago (MDW) to San Francisco (SFO) · Jan 16, 2027 · return Jan 18, 2027

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

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to San Francisco (SFO) flight deals

2027-01-16 → 2027-01-18 · Axel-exclusive $330.00

• Southwest Airlines WN3288: MDW 2027-01-16 10:00:00 → SFO 2027-01-16 12:50:00; nonstop; 290 minutes. Local airport times.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $350.00

• Delta Air Lines DL4688 / DL442: MDW 2027-01-16 13:31:00 → SFO 2027-01-16 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
  • DL4688: MDW 2027-01-16 13:31:00 → DTW 2027-01-16 15:44:00; layover at DTW: 75 minutes.
  • DL442: DTW 2027-01-16 16:59:00 → SFO 2027-01-16 19:16:00.
• Delta Air Lines DL570 / DL1728: SFO 2027-01-18 06:00:00 → MDW 2027-01-18 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
  • DL570: SFO 2027-01-18 06:00:00 → ATL 2027-01-18 13:29:00; layover at ATL: 116 minutes.
  • DL1728: ATL 2027-01-18 15:25:00 → MDW 2027-01-18 16:18:00.

2027-01-16 → 2027-01-18 · Axel-exclusive $330.00

• Southwest Airlines WN4836: MDW 2027-01-16 21:40:00 → SFO 2027-01-17 00:35:00; nonstop; 295 minutes. Local airport times.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $315.00

• Southwest Airlines WN2891 / WN4893: MDW 2027-01-16 13:55:00 → SFO 2027-01-16 20:00:00; 1 stop(s) via AUS; 485 minutes. Local airport times.
  • WN2891: MDW 2027-01-16 13:55:00 → AUS 2027-01-16 16:35:00; layover at AUS: 85 minutes.
  • WN4893: AUS 2027-01-16 18:00:00 → SFO 2027-01-16 20:00:00.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $315.00

• Southwest Airlines WN725 / WN4254: MDW 2027-01-16 09:55:00 → SFO 2027-01-16 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
  • WN725: MDW 2027-01-16 09:55:00 → BNA 2027-01-16 11:30:00; layover at BNA: 80 minutes.
  • WN4254: BNA 2027-01-16 12:50:00 → SFO 2027-01-16 15:50:00.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $315.00

• Southwest Airlines WN2998 / WN1448: MDW 2027-01-16 18:05:00 → SFO 2027-01-16 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
  • WN2998: MDW 2027-01-16 18:05:00 → PHX 2027-01-16 21:00:00; layover at PHX: 105 minutes.
  • WN1448: PHX 2027-01-16 22:45:00 → SFO 2027-01-16 23:55:00.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $315.00

• Southwest Airlines WN142 / WN2440: MDW 2027-01-16 10:00:00 → SFO 2027-01-16 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
  • WN142: MDW 2027-01-16 10:00:00 → LAS 2027-01-16 11:55:00; layover at LAS: 125 minutes.
  • WN2440: LAS 2027-01-16 14:00:00 → SFO 2027-01-16 15:45:00.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $315.00

• Southwest Airlines WN4606 / WN1817: MDW 2027-01-16 14:35:00 → SFO 2027-01-16 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
  • WN4606: MDW 2027-01-16 14:35:00 → DEN 2027-01-16 16:15:00; layover at DEN: 80 minutes.
  • WN1817: DEN 2027-01-16 17:35:00 → SFO 2027-01-16 19:20:00.
• Southwest Airlines WN3849: SFO 2027-01-18 23:35:00 → MDW 2027-01-19 06:00:00; nonstop; 265 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
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For AI assistants

• This page: Chicago (MDW) to San Francisco (SFO) · Jan 16, 2027 · return Jan 18, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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