Chicago (MDW) to San Jose (SJC) · Dec 6, 2026 · one way

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

2026-12-06 · one way · Axel-exclusive $180.00

• Southwest Airlines WN2386: MDW 2026-12-06 15:50:00 → SJC 2026-12-06 18:30:00; nonstop; 280 minutes. Local airport times.

2026-12-06 · one way · Axel-exclusive $180.00

• Southwest Airlines WN3035: MDW 2026-12-06 09:55:00 → SJC 2026-12-06 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2905 / WN2917: MDW 2026-12-06 09:55:00 → SJC 2026-12-06 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-12-06 09:55:00 → BUR 2026-12-06 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-12-06 15:30:00 → SJC 2026-12-06 16:50:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4415 / WN3749: MDW 2026-12-06 15:15:00 → SJC 2026-12-06 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-12-06 19:30:00 → SJC 2026-12-06 21:00:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN1517 / WN2538: MDW 2026-12-06 10:05:00 → SJC 2026-12-06 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-12-06 10:05:00 → LAX 2026-12-06 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-12-06 14:45:00 → SJC 2026-12-06 16:00:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2998 / WN3507: MDW 2026-12-06 18:05:00 → SJC 2026-12-06 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-12-06 18:05:00 → PHX 2026-12-06 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-12-06 22:20:00 → SJC 2026-12-06 23:20:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN725 / WN364: MDW 2026-12-06 09:55:00 → SJC 2026-12-06 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-12-06 09:55:00 → BNA 2026-12-06 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-12-06 13:55:00 → SJC 2026-12-06 16:45:00.

2026-12-06 · one way · Axel-exclusive $165.00

• Southwest Airlines WN142 / WN1226: MDW 2026-12-06 10:00:00 → SJC 2026-12-06 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2026-12-06 10:00:00 → LAS 2026-12-06 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2026-12-06 13:20:00 → SJC 2026-12-06 14:55:00.

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
• Dec 5, 2026 · Return options
• Dec 7, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Dec 6, 2026 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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