Chicago (MDW) to San Jose (SJC) · Dec 24, 2026 · return Jan 7, 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 Jose (SJC) flight deals

2026-12-24 → 2027-01-07 · Axel-exclusive $376.00

• Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $376.00

• Southwest Airlines WN142 / WN1226: MDW 2026-12-24 10:00:00 → SJC 2026-12-24 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2026-12-24 10:00:00 → LAS 2026-12-24 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2026-12-24 13:20:00 → SJC 2026-12-24 14:55:00.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $376.00

• Southwest Airlines WN2905 / WN2917: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-12-24 09:55:00 → BUR 2026-12-24 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-12-24 15:30:00 → SJC 2026-12-24 16:50:00.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $376.00

• Southwest Airlines WN4415 / WN3749: MDW 2026-12-24 15:15:00 → SJC 2026-12-24 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-12-24 15:15:00 → SAN 2026-12-24 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-12-24 19:30:00 → SJC 2026-12-24 21:00:00.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $376.00

• Southwest Airlines WN2998 / WN3507: MDW 2026-12-24 18:05:00 → SJC 2026-12-24 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-12-24 18:05:00 → PHX 2026-12-24 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-12-24 22:20:00 → SJC 2026-12-24 23:20:00.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $397.00

• Southwest Airlines WN3035: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.

Explore this route

• All dates for this route
• Dec 23, 2026 · Return options
• Dec 25, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Dec 24, 2026 · return Jan 7, 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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