Chicago (MDW) to San Jose (SJC) · Jan 26, 2027 · return Feb 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

2027-01-26 → 2027-02-01 · Axel-exclusive $332.50

• Southwest Airlines WN2386: MDW 2027-01-26 15:50:00 → SJC 2027-01-26 18:30:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $332.50

• Southwest Airlines WN3035: MDW 2027-01-26 10:10:00 → SJC 2027-01-26 12:55:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN2998 / WN3507: MDW 2027-01-26 18:05:00 → SJC 2027-01-26 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2027-01-26 18:05:00 → PHX 2027-01-26 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2027-01-26 22:20:00 → SJC 2027-01-26 23:20:00.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN4415 / WN3749: MDW 2027-01-26 15:15:00 → SJC 2027-01-26 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2027-01-26 15:15:00 → SAN 2027-01-26 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2027-01-26 19:30:00 → SJC 2027-01-26 21:00:00.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN3035: MDW 2027-01-26 09:55:00 → SJC 2027-01-26 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3883 / WN2133: SJC 2027-02-01 07:45:00 → MDW 2027-02-01 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
  • WN3883: SJC 2027-02-01 07:45:00 → HOU 2027-02-01 13:20:00; layover at HOU: 75 minutes.
  • WN2133: HOU 2027-02-01 14:35:00 → MDW 2027-02-01 17:00:00.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN725 / WN364: MDW 2027-01-26 09:55:00 → SJC 2027-01-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2027-01-26 09:55:00 → BNA 2027-01-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2027-01-26 13:55:00 → SJC 2027-01-26 16:45:00.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN1517 / WN2538: MDW 2027-01-26 10:05:00 → SJC 2027-01-26 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2027-01-26 10:05:00 → LAX 2027-01-26 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2027-01-26 14:45:00 → SJC 2027-01-26 16:00:00.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.25

• Southwest Airlines WN142 / WN1226: MDW 2027-01-26 10:00:00 → SJC 2027-01-26 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2027-01-26 10:00:00 → LAS 2027-01-26 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2027-01-26 13:20:00 → SJC 2027-01-26 14:55:00.
• Southwest Airlines WN4230: SJC 2027-02-01 23:00:00 → MDW 2027-02-02 05:00:00; nonstop; 240 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 25, 2027 · Return options
• Jan 27, 2027 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Jan 26, 2027 · return Feb 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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• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to San Jose (SJC) flight deals · Flight search guide.
• 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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