San Jose (SJC) to Chicago (MDW) · Jan 2, 2027 · return Jan 8, 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

2027-01-02 → 2027-01-08 · Axel-exclusive $406.00

• Southwest Airlines WN576: SJC 2027-01-02 11:10:00 → MDW 2027-01-02 17:15:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $406.00

• Southwest Airlines WN3895: SJC 2027-01-02 23:00:00 → MDW 2027-01-03 05:00:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN433 / WN801: SJC 2027-01-02 07:20:00 → MDW 2027-01-02 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2027-01-02 07:20:00 → LGB 2027-01-02 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2027-01-02 11:35:00 → MDW 2027-01-02 17:20:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN3818 / WN2518: SJC 2027-01-02 20:05:00 → MDW 2027-01-03 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2027-01-02 20:05:00 → LAX 2027-01-02 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2027-01-02 23:55:00 → MDW 2027-01-03 05:55:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN2612 / WN4975: SJC 2027-01-02 20:45:00 → MDW 2027-01-03 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2027-01-02 20:45:00 → SEA 2027-01-02 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2027-01-03 00:15:00 → MDW 2027-01-03 06:05:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN3877 / WN776: SJC 2027-01-02 13:40:00 → MDW 2027-01-02 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2027-01-02 13:40:00 → DEN 2027-01-02 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2027-01-02 18:05:00 → MDW 2027-01-02 21:30:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN3901 / WN696: SJC 2027-01-02 07:15:00 → MDW 2027-01-02 17:05:00; 1 stop(s) via PDX; 470 minutes. Local airport times.
  • WN3901: SJC 2027-01-02 07:15:00 → PDX 2027-01-02 09:05:00; layover at PDX: 135 minutes.
  • WN696: PDX 2027-01-02 11:20:00 → MDW 2027-01-02 17:05:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-08 · Axel-exclusive $382.03

• Southwest Airlines WN3883 / WN2133: SJC 2027-01-02 07:45:00 → MDW 2027-01-02 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
  • WN3883: SJC 2027-01-02 07:45:00 → HOU 2027-01-02 13:20:00; layover at HOU: 75 minutes.
  • WN2133: HOU 2027-01-02 14:35:00 → MDW 2027-01-02 17:00:00.
• Southwest Airlines WN3035: MDW 2027-01-08 09:55:00 → SJC 2027-01-08 12:35:00; nonstop; 280 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 1, 2027 · Return options
• Jan 3, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (MDW) · Jan 2, 2027 · return Jan 8, 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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