Chicago (MDW) to San Jose (SJC) · Dec 27, 2026 · return Jan 1, 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

2026-12-27 → 2027-01-01 · Axel-exclusive $477.75

• Southwest Airlines WN3035: MDW 2026-12-27 10:10:00 → SJC 2026-12-27 12:55:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN576: SJC 2027-01-01 11:10:00 → MDW 2027-01-01 17:15:00; nonstop; 245 minutes. Local airport times.

2026-12-27 → 2027-01-01 · Axel-exclusive $436.80

• Southwest Airlines WN725 / WN364: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-12-27 09:55:00 → BNA 2026-12-27 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-12-27 13:55:00 → SJC 2026-12-27 16:45:00.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

2026-12-27 → 2027-01-01 · Axel-exclusive $436.80

• Southwest Airlines WN2905 / WN2917: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-12-27 09:55:00 → BUR 2026-12-27 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-12-27 15:30:00 → SJC 2026-12-27 16:50:00.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

2026-12-27 → 2027-01-01 · Axel-exclusive $436.80

• Southwest Airlines WN2998 / WN3507: MDW 2026-12-27 18:05:00 → SJC 2026-12-27 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-12-27 18:05:00 → PHX 2026-12-27 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-12-27 22:20:00 → SJC 2026-12-27 23:20:00.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

2026-12-27 → 2027-01-01 · Axel-exclusive $436.80

• Southwest Airlines WN1517 / WN2538: MDW 2026-12-27 10:05:00 → SJC 2026-12-27 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-12-27 10:05:00 → LAX 2026-12-27 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-12-27 14:45:00 → SJC 2026-12-27 16:00:00.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

2026-12-27 → 2027-01-01 · Axel-exclusive $436.80

• Southwest Airlines WN4415 / WN3749: MDW 2026-12-27 15:15:00 → SJC 2026-12-27 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-12-27 15:15:00 → SAN 2026-12-27 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-12-27 19:30:00 → SJC 2026-12-27 21:00:00.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

2026-12-27 → 2027-01-01 · Axel-exclusive $457.80

• Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00.

Explore this route

• All dates for this route
• Dec 26, 2026 · Return options
• Dec 28, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Dec 27, 2026 · return Jan 1, 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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