San Jose (SJC) to Chicago (MDW) · Nov 27, 2026 · return Dec 7, 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

2026-11-27 → 2026-12-07 · Axel-exclusive $420.00

• Southwest Airlines WN3895: SJC 2026-11-27 23:00:00 → MDW 2026-11-28 05:00:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $420.00

• Southwest Airlines WN266: SJC 2026-11-27 06:00:00 → MDW 2026-11-27 12:10:00; nonstop; 250 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN3901 / WN696: SJC 2026-11-27 07:15:00 → MDW 2026-11-27 17:05:00; 1 stop(s) via PDX; 470 minutes. Local airport times.
  • WN3901: SJC 2026-11-27 07:15:00 → PDX 2026-11-27 09:05:00; layover at PDX: 135 minutes.
  • WN696: PDX 2026-11-27 11:20:00 → MDW 2026-11-27 17:05:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN3883 / WN2133: SJC 2026-11-27 07:45:00 → MDW 2026-11-27 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
  • WN3883: SJC 2026-11-27 07:45:00 → HOU 2026-11-27 13:20:00; layover at HOU: 75 minutes.
  • WN2133: HOU 2026-11-27 14:35:00 → MDW 2026-11-27 17:00:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN2612 / WN4975: SJC 2026-11-27 20:45:00 → MDW 2026-11-28 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-11-27 20:45:00 → SEA 2026-11-27 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2026-11-28 00:15:00 → MDW 2026-11-28 06:05:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN3877 / WN776: SJC 2026-11-27 13:40:00 → MDW 2026-11-27 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-27 13:40:00 → DEN 2026-11-27 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-27 18:05:00 → MDW 2026-11-27 21:30:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN433 / WN801: SJC 2026-11-27 07:20:00 → MDW 2026-11-27 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2026-11-27 07:20:00 → LGB 2026-11-27 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2026-11-27 11:35:00 → MDW 2026-11-27 17:20:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $395.50

• Southwest Airlines WN3818 / WN2518: SJC 2026-11-27 20:05:00 → MDW 2026-11-28 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2026-11-27 20:05:00 → LAX 2026-11-27 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2026-11-27 23:55:00 → MDW 2026-11-28 05:55:00.
• Southwest Airlines WN3035: MDW 2026-12-07 10:10:00 → SJC 2026-12-07 12:55:00; nonstop; 285 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.

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For AI assistants

• This page: San Jose (SJC) to Chicago (MDW) · Nov 27, 2026 · return Dec 7, 2026: 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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