San Francisco (SFO) to Chicago (MDW), Jan 22–24, 2027: from $152 one way

San Francisco (SFO) to Chicago (MDW), Jan 22–24, 2027: from $152 one way on Axel, checked Oct 29, 2026. Lowest published fare: $152 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 22, 2027, 1 adult, economy, checked Oct 29, 2026. 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

2027-01-24 · one way · Axel-exclusive $171.00

• Southwest Airlines WN2331: SFO 2027-01-24 06:00:00 → MDW 2027-01-24 12:15:00; nonstop; 255 minutes. Local airport times.

2027-01-24 · one way · Axel-exclusive $194.75

• Delta Air Lines DL570 / DL1728: SFO 2027-01-24 06:00:00 → MDW 2027-01-24 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
  • DL570: SFO 2027-01-24 06:00:00 → ATL 2027-01-24 13:29:00; layover at ATL: 116 minutes.
  • DL1728: ATL 2027-01-24 15:25:00 → MDW 2027-01-24 16:18:00.

2027-01-23 · one way · Axel-exclusive $171.00

• Southwest Airlines WN2331: SFO 2027-01-23 06:00:00 → MDW 2027-01-23 12:15:00; nonstop; 255 minutes. Local airport times.

2027-01-22 · one way · Axel-exclusive $171.00

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

2027-01-24 · one way · Axel-exclusive $171.00

• Southwest Airlines WN3849: SFO 2027-01-24 23:35:00 → MDW 2027-01-25 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-22 · one way · Axel-exclusive $171.00

• Southwest Airlines WN3849: SFO 2027-01-22 23:35:00 → MDW 2027-01-23 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-23 · one way · Axel-exclusive $171.00

• Southwest Airlines WN3849: SFO 2027-01-23 23:35:00 → MDW 2027-01-24 06:00:00; nonstop; 265 minutes. Local airport times.

2027-01-23 · one way · Axel-exclusive $152.00

• Southwest Airlines WN2749 / WN4963: SFO 2027-01-23 20:20:00 → MDW 2027-01-24 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
  • WN2749: SFO 2027-01-23 20:20:00 → PHX 2027-01-23 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2027-01-24 01:35:00 → MDW 2027-01-24 05:45:00.

2027-01-23 · one way · Axel-exclusive $152.00

• Southwest Airlines WN3847 / WN2515: SFO 2027-01-23 08:20:00 → MDW 2027-01-23 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
  • WN3847: SFO 2027-01-23 08:20:00 → LAX 2027-01-23 09:50:00; layover at LAX: 85 minutes.
  • WN2515: LAX 2027-01-23 11:15:00 → MDW 2027-01-23 17:15:00.

2027-01-24 · one way · Axel-exclusive $152.00

• Southwest Airlines WN2989 / WN4770: SFO 2027-01-24 13:05:00 → MDW 2027-01-24 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
  • WN2989: SFO 2027-01-24 13:05:00 → STL 2027-01-24 18:55:00; layover at STL: 175 minutes.
  • WN4770: STL 2027-01-24 21:50:00 → MDW 2027-01-24 23:00:00.

2027-01-22 · one way · Axel-exclusive $152.00

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

2027-01-22 · one way · Axel-exclusive $152.00

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

2027-01-24 · one way · Axel-exclusive $152.00

• Southwest Airlines WN3847 / WN2515: SFO 2027-01-24 08:20:00 → MDW 2027-01-24 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
  • WN3847: SFO 2027-01-24 08:20:00 → LAX 2027-01-24 09:50:00; layover at LAX: 85 minutes.
  • WN2515: LAX 2027-01-24 11:15:00 → MDW 2027-01-24 17:15:00.

2027-01-24 · one way · Axel-exclusive $152.00

• Southwest Airlines WN2749 / WN4963: SFO 2027-01-24 20:20:00 → MDW 2027-01-25 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
  • WN2749: SFO 2027-01-24 20:20:00 → PHX 2027-01-24 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2027-01-25 01:35:00 → MDW 2027-01-25 05:45:00.

2027-01-22 · one way · Axel-exclusive $152.00

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

2027-01-23 · one way · Axel-exclusive $152.00

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

2027-01-22 · one way · Axel-exclusive $152.00

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

2027-01-24 · one way · Axel-exclusive $152.00

• Southwest Airlines WN3428 / WN1699: SFO 2027-01-24 08:00:00 → MDW 2027-01-24 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
  • WN3428: SFO 2027-01-24 08:00:00 → DEN 2027-01-24 11:30:00; layover at DEN: 190 minutes.
  • WN1699: DEN 2027-01-24 14:40:00 → MDW 2027-01-24 17:55:00.

2027-01-23 · one way · Axel-exclusive $152.00

• Southwest Airlines WN3428 / WN1699: SFO 2027-01-23 08:00:00 → MDW 2027-01-23 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
  • WN3428: SFO 2027-01-23 08:00:00 → DEN 2027-01-23 11:30:00; layover at DEN: 190 minutes.
  • WN1699: DEN 2027-01-23 14:40:00 → MDW 2027-01-23 17:55:00.

2027-01-23 · one way · Axel-exclusive $194.75

• Delta Air Lines DL570 / DL1728: SFO 2027-01-23 06:00:00 → MDW 2027-01-23 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
  • DL570: SFO 2027-01-23 06:00:00 → ATL 2027-01-23 13:29:00; layover at ATL: 116 minutes.
  • DL1728: ATL 2027-01-23 15:25:00 → MDW 2027-01-23 16:18:00.

2027-01-22 · one way · Axel-exclusive $194.75

• Delta Air Lines DL2178 / DL4714: SFO 2027-01-22 06:00:00 → MDW 2027-01-22 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
  • DL2178: SFO 2027-01-22 06:00:00 → MSP 2027-01-22 11:40:00; layover at MSP: 200 minutes.
  • DL4714: MSP 2027-01-22 15:00:00 → MDW 2027-01-22 16:39:00.

2027-01-22 · one way · Axel-exclusive $194.75

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

2027-01-24 · one way · Axel-exclusive $194.75

• Delta Air Lines DL2178 / DL4714: SFO 2027-01-24 06:00:00 → MDW 2027-01-24 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
  • DL2178: SFO 2027-01-24 06:00:00 → MSP 2027-01-24 11:40:00; layover at MSP: 200 minutes.
  • DL4714: MSP 2027-01-24 15:00:00 → MDW 2027-01-24 16:39:00.

2027-01-23 · one way · Axel-exclusive $194.75

• Delta Air Lines DL2178 / DL4714: SFO 2027-01-23 06:00:00 → MDW 2027-01-23 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
  • DL2178: SFO 2027-01-23 06:00:00 → MSP 2027-01-23 11:40:00; layover at MSP: 200 minutes.
  • DL4714: MSP 2027-01-23 15:00:00 → MDW 2027-01-23 16:39:00.

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.

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