San Francisco (SFO) to Chicago (MDW) · Jan 8, 2027 · return Jan 22, 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: San Francisco Bay Area to Chicago (MDW) flight deals

2027-01-08 → 2027-01-22 · Axel-exclusive $332.50

• Southwest Airlines WN2331: SFO 2027-01-08 06:00:00 → MDW 2027-01-08 12:15:00; nonstop; 255 minutes. Local airport times.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $370.50

• Delta Air Lines DL570 / DL1728: SFO 2027-01-08 06:00:00 → MDW 2027-01-08 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
  • DL570: SFO 2027-01-08 06:00:00 → ATL 2027-01-08 13:29:00; layover at ATL: 116 minutes.
  • DL1728: ATL 2027-01-08 15:25:00 → MDW 2027-01-08 16:18:00.
• Delta Air Lines DL4688 / DL442: MDW 2027-01-22 13:31:00 → SFO 2027-01-22 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
  • DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 75 minutes.
  • DL442: DTW 2027-01-22 16:59:00 → SFO 2027-01-22 19:16:00.

2027-01-08 → 2027-01-22 · Axel-exclusive $332.50

• Southwest Airlines WN3849: SFO 2027-01-08 23:35:00 → MDW 2027-01-09 06:00:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $313.50

• Southwest Airlines WN3847 / WN2515: SFO 2027-01-08 08:20:00 → MDW 2027-01-08 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
  • WN3847: SFO 2027-01-08 08:20:00 → LAX 2027-01-08 09:50:00; layover at LAX: 85 minutes.
  • WN2515: LAX 2027-01-08 11:15:00 → MDW 2027-01-08 17:15:00.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $313.50

• Southwest Airlines WN2989 / WN4770: SFO 2027-01-08 13:05:00 → MDW 2027-01-08 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
  • WN2989: SFO 2027-01-08 13:05:00 → STL 2027-01-08 18:55:00; layover at STL: 175 minutes.
  • WN4770: STL 2027-01-08 21:50:00 → MDW 2027-01-08 23:00:00.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $313.50

• Southwest Airlines WN3428 / WN1699: SFO 2027-01-08 08:00:00 → MDW 2027-01-08 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
  • WN3428: SFO 2027-01-08 08:00:00 → DEN 2027-01-08 11:30:00; layover at DEN: 190 minutes.
  • WN1699: DEN 2027-01-08 14:40:00 → MDW 2027-01-08 17:55:00.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $313.50

• Southwest Airlines WN2749 / WN4963: SFO 2027-01-08 20:20:00 → MDW 2027-01-09 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
  • WN2749: SFO 2027-01-08 20:20:00 → PHX 2027-01-08 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2027-01-09 01:35:00 → MDW 2027-01-09 05:45:00.
• Southwest Airlines WN786: MDW 2027-01-22 09:55:00 → SFO 2027-01-22 12:45:00; nonstop; 290 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $370.50

• Delta Air Lines DL2178 / DL4714: SFO 2027-01-08 06:00:00 → MDW 2027-01-08 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
  • DL2178: SFO 2027-01-08 06:00:00 → MSP 2027-01-08 11:40:00; layover at MSP: 200 minutes.
  • DL4714: MSP 2027-01-08 15:00:00 → MDW 2027-01-08 16:39:00.
• Delta Air Lines DL4688 / DL442: MDW 2027-01-22 13:31:00 → SFO 2027-01-22 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
  • DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 75 minutes.
  • DL442: DTW 2027-01-22 16:59:00 → SFO 2027-01-22 19:16:00.

Explore this route

• All dates for this route
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Francisco (SFO) to Chicago (MDW) · Jan 8, 2027 · return Jan 22, 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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