Chicago (MDW) to San Jose (SJC) · Nov 21, 2026 · return Nov 26, 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: Chicago to San Jose (SJC) flight deals

2026-11-21 → 2026-11-26 · Axel-exclusive $432.00

• Southwest Airlines WN2905 / WN2917: MDW 2026-11-21 09:55:00 → SJC 2026-11-21 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-11-21 09:55:00 → BUR 2026-11-21 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-11-21 15:30:00 → SJC 2026-11-21 16:50:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-21 → 2026-11-26 · Axel-exclusive $432.00

• Southwest Airlines WN2998 / WN3507: MDW 2026-11-21 18:05:00 → SJC 2026-11-21 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-11-21 18:05:00 → PHX 2026-11-21 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-11-21 22:20:00 → SJC 2026-11-21 23:20:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-21 → 2026-11-26 · Axel-exclusive $432.00

• Southwest Airlines WN142 / WN1226: MDW 2026-11-21 10:00:00 → SJC 2026-11-21 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2026-11-21 10:00:00 → LAS 2026-11-21 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2026-11-21 13:20:00 → SJC 2026-11-21 14:55:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-21 → 2026-11-26 · Axel-exclusive $432.00

• Southwest Airlines WN4415 / WN3749: MDW 2026-11-21 15:15:00 → SJC 2026-11-21 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-11-21 15:15:00 → SAN 2026-11-21 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-11-21 19:30:00 → SJC 2026-11-21 21:00:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-21 → 2026-11-26 · Axel-exclusive $432.00

• Southwest Airlines WN1517 / WN2538: MDW 2026-11-21 10:05:00 → SJC 2026-11-21 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-11-21 10:05:00 → LAX 2026-11-21 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-11-21 14:45:00 → SJC 2026-11-21 16:00:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-21 → 2026-11-26 · Axel-exclusive $452.25

• Southwest Airlines WN3035: MDW 2026-11-21 10:15:00 → SJC 2026-11-21 13:00:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

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.

Explore this route

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 21, 2026 · return Nov 26, 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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