San Jose (SJC) to Chicago (MDW) · Dec 31, 2026 · return Jan 5, 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: San Francisco Bay Area to Chicago (MDW) flight deals

2026-12-31 → 2027-01-05 · Axel-exclusive $420.00

• Southwest Airlines WN576: SJC 2026-12-31 11:10:00 → MDW 2026-12-31 17:15:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $420.00

• Southwest Airlines WN3895: SJC 2026-12-31 23:00:00 → MDW 2027-01-01 05:00:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN3901 / WN696: SJC 2026-12-31 07:15:00 → MDW 2026-12-31 17:05:00; 1 stop(s) via PDX; 470 minutes. Local airport times.
  • WN3901: SJC 2026-12-31 07:15:00 → PDX 2026-12-31 09:05:00; layover at PDX: 135 minutes.
  • WN696: PDX 2026-12-31 11:20:00 → MDW 2026-12-31 17:05:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN3818 / WN2518: SJC 2026-12-31 20:05:00 → MDW 2027-01-01 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2026-12-31 20:05:00 → LAX 2026-12-31 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2026-12-31 23:55:00 → MDW 2027-01-01 05:55:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN2612 / WN4975: SJC 2026-12-31 20:45:00 → MDW 2027-01-01 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-12-31 20:45:00 → SEA 2026-12-31 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-01 00:15:00 → MDW 2027-01-01 06:05:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN3883 / WN2133: SJC 2026-12-31 07:45:00 → MDW 2026-12-31 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
  • WN3883: SJC 2026-12-31 07:45:00 → HOU 2026-12-31 13:20:00; layover at HOU: 75 minutes.
  • WN2133: HOU 2026-12-31 14:35:00 → MDW 2026-12-31 17:00:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN3877 / WN776: SJC 2026-12-31 13:40:00 → MDW 2026-12-31 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-31 13:40:00 → DEN 2026-12-31 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-31 18:05:00 → MDW 2026-12-31 21:30:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

2026-12-31 → 2027-01-05 · Axel-exclusive $394.63

• Southwest Airlines WN433 / WN801: SJC 2026-12-31 07:20:00 → MDW 2026-12-31 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2026-12-31 07:20:00 → LGB 2026-12-31 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2026-12-31 11:35:00 → MDW 2026-12-31 17:20:00.
• Southwest Airlines WN3035: MDW 2027-01-05 10:10:00 → SJC 2027-01-05 12:55:00; nonstop; 285 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (MDW) · Dec 31, 2026 · return Jan 5, 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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• 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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