Chicago (MDW) to San Jose (SJC), Nov 22, 2026 – Dec 3, 2026: from $376 round trip

Chicago (MDW) to San Jose (SJC), Nov 22, 2026 – Dec 3, 2026: from $376 round trip on Axel, checked Nov 15, 2026. Lowest published fare: $376 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 22, 2026 – Dec 3, 2026, 1 adult, economy, checked Nov 15, 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.

Hotels in San Jose, California for these trips

Hotels: under a trip, hotels in San Jose, California for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in San Jose, California for these nights (Nov 22 – Dec 3, 2026 · 11 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $94 a night, $1,030 for 11 nights · 4★ The Domain Hotel, $111 a night, $1,221 for 11 nights

All hotels in San Jose, California

Route overview: Chicago to San Jose (SJC) flight deals

2026-11-22 → 2026-12-03 · Axel-exclusive $376

• Southwest Airlines WN142 / WN1226: MDW 2026-11-22 10:00:00 → SJC 2026-11-22 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2026-11-22 10:00:00 → LAS 2026-11-22 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2026-11-22 13:20:00 → SJC 2026-11-22 14:55:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $376

• Southwest Airlines WN2905 / WN2917: MDW 2026-11-22 09:55:00 → SJC 2026-11-22 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-11-22 09:55:00 → BUR 2026-11-22 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-11-22 15:30:00 → SJC 2026-11-22 16:50:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $376

• Southwest Airlines WN725 / WN364: MDW 2026-11-22 09:55:00 → SJC 2026-11-22 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-22 09:55:00 → BNA 2026-11-22 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-22 13:55:00 → SJC 2026-11-22 16:45:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $376

• Southwest Airlines WN4415 / WN3749: MDW 2026-11-22 15:15:00 → SJC 2026-11-22 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-11-22 15:15:00 → SAN 2026-11-22 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-11-22 19:30:00 → SJC 2026-11-22 21:00:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $376

• Southwest Airlines WN1517 / WN2538: MDW 2026-11-22 10:05:00 → SJC 2026-11-22 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-11-22 10:05:00 → LAX 2026-11-22 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-11-22 14:45:00 → SJC 2026-11-22 16:00:00.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $396

• Southwest Airlines WN3035: MDW 2026-11-22 09:55:00 → SJC 2026-11-22 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 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 21, 2026 · Return options
• Nov 23, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 22, 2026 · return Dec 3, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in San Jose, California for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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