Chicago (MDW) to San Jose (SJC) · Jan 5, 2027 · return Jan 9, 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

2027-01-05 → 2027-01-09 · Axel-exclusive $332.50

• Southwest Airlines WN2386: MDW 2027-01-05 15:50:00 → SJC 2027-01-05 18:30:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $332.50

• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN1517 / WN2538: MDW 2027-01-05 10:05:00 → SJC 2027-01-05 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2027-01-05 10:05:00 → LAX 2027-01-05 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2027-01-05 14:45:00 → SJC 2027-01-05 16:00:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN4415 / WN3749: MDW 2027-01-05 15:15:00 → SJC 2027-01-05 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2027-01-05 15:15:00 → SAN 2027-01-05 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2027-01-05 19:30:00 → SJC 2027-01-05 21:00:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN3035: MDW 2027-01-05 09:55:00 → SJC 2027-01-05 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3818 / WN2518: SJC 2027-01-09 20:05:00 → MDW 2027-01-10 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2027-01-09 20:05:00 → LAX 2027-01-09 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2027-01-09 23:55:00 → MDW 2027-01-10 05:55:00.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN725 / WN364: MDW 2027-01-05 09:55:00 → SJC 2027-01-05 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2027-01-05 09:55:00 → BNA 2027-01-05 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2027-01-05 13:55:00 → SJC 2027-01-05 16:45:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN2998 / WN3507: MDW 2027-01-05 18:05:00 → SJC 2027-01-05 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2027-01-05 18:05:00 → PHX 2027-01-05 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2027-01-05 22:20:00 → SJC 2027-01-05 23:20:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-05 → 2027-01-09 · Axel-exclusive $318.25

• Southwest Airlines WN142 / WN1226: MDW 2027-01-05 10:00:00 → SJC 2027-01-05 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2027-01-05 10:00:00 → LAS 2027-01-05 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2027-01-05 13:20:00 → SJC 2027-01-05 14:55:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 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.

Explore this route

• All dates for this route
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For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Jan 5, 2027 · return Jan 9, 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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