San Diego (SAN) 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 Diego to Chicago (MDW) flight deals

2027-01-02 → 2027-01-08 · Axel-exclusive $370.51

• Southwest Airlines WN4669 / WN651: SAN 2027-01-02 11:55:00 → MDW 2027-01-02 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2027-01-02 11:55:00 → BNA 2027-01-02 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2027-01-02 19:30:00 → MDW 2027-01-02 21:05:00.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

2027-01-02 → 2027-01-08 · Axel-exclusive $370.51

• Southwest Airlines WN3681 / WN295: SAN 2027-01-02 08:10:00 → MDW 2027-01-02 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
  • WN3681: SAN 2027-01-02 08:10:00 → AUS 2027-01-02 13:00:00; layover at AUS: 110 minutes.
  • WN295: AUS 2027-01-02 14:50:00 → MDW 2027-01-02 17:20:00.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

2027-01-02 → 2027-01-08 · Axel-exclusive $370.51

• Southwest Airlines WN3699 / WN776: SAN 2027-01-02 12:30:00 → MDW 2027-01-02 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
  • WN3699: SAN 2027-01-02 12:30:00 → DEN 2027-01-02 15:50:00; layover at DEN: 135 minutes.
  • WN776: DEN 2027-01-02 18:05:00 → MDW 2027-01-02 21:30:00.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

2027-01-02 → 2027-01-08 · Axel-exclusive $370.51

• Southwest Airlines WN399 / WN1407: SAN 2027-01-02 12:10:00 → MDW 2027-01-02 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
  • WN399: SAN 2027-01-02 12:10:00 → OMA 2027-01-02 17:15:00; layover at OMA: 65 minutes.
  • WN1407: OMA 2027-01-02 18:20:00 → MDW 2027-01-02 19:45:00.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

2027-01-02 → 2027-01-08 · Axel-exclusive $370.51

• Southwest Airlines WN4711 / WN4175: SAN 2027-01-02 11:55:00 → MDW 2027-01-02 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
  • WN4711: SAN 2027-01-02 11:55:00 → STL 2027-01-02 17:25:00; layover at STL: 90 minutes.
  • WN4175: STL 2027-01-02 18:55:00 → MDW 2027-01-02 20:00:00.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

2027-01-02 → 2027-01-08 · Axel-exclusive $390.46

• Southwest Airlines WN634: SAN 2027-01-02 08:15:00 → MDW 2027-01-02 14:15:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN1354 / WN225: MDW 2027-01-08 13:20:00 → SAN 2027-01-08 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-08 13:20:00 → CMH 2027-01-08 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-08 16:45:00 → SAN 2027-01-08 18:35:00.

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 Diego (SAN) 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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