San Diego (SAN) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 2026

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

2026-11-25 → 2026-12-05 · Axel-exclusive $417.13

• Southwest Airlines WN126: SAN 2026-11-25 11:25:00 → MDW 2026-11-25 17:25:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $417.13

• Southwest Airlines WN1011: SAN 2026-11-25 22:40:00 → MDW 2026-11-26 04:25:00; nonstop; 225 minutes. Local airport times.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN3752 / WN4349: SAN 2026-11-25 08:25:00 → MDW 2026-11-25 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
  • WN3752: SAN 2026-11-25 08:25:00 → SLC 2026-11-25 11:35:00; layover at SLC: 70 minutes.
  • WN4349: SLC 2026-11-25 12:45:00 → MDW 2026-11-25 16:45:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN399 / WN1407: SAN 2026-11-25 12:10:00 → MDW 2026-11-25 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
  • WN399: SAN 2026-11-25 12:10:00 → OMA 2026-11-25 17:15:00; layover at OMA: 65 minutes.
  • WN1407: OMA 2026-11-25 18:20:00 → MDW 2026-11-25 19:45:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN3681 / WN295: SAN 2026-11-25 08:10:00 → MDW 2026-11-25 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
  • WN3681: SAN 2026-11-25 08:10:00 → AUS 2026-11-25 13:00:00; layover at AUS: 110 minutes.
  • WN295: AUS 2026-11-25 14:50:00 → MDW 2026-11-25 17:20:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN3699 / WN776: SAN 2026-11-25 12:30:00 → MDW 2026-11-25 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
  • WN3699: SAN 2026-11-25 12:30:00 → DEN 2026-11-25 15:50:00; layover at DEN: 135 minutes.
  • WN776: DEN 2026-11-25 18:05:00 → MDW 2026-11-25 21:30:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN4669 / WN651: SAN 2026-11-25 11:55:00 → MDW 2026-11-25 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2026-11-25 11:55:00 → BNA 2026-11-25 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2026-11-25 19:30:00 → MDW 2026-11-25 21:05:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $396.88

• Southwest Airlines WN4711 / WN4175: SAN 2026-11-25 11:55:00 → MDW 2026-11-25 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
  • WN4711: SAN 2026-11-25 11:55:00 → STL 2026-11-25 17:25:00; layover at STL: 90 minutes.
  • WN4175: STL 2026-11-25 18:55:00 → MDW 2026-11-25 20:00:00.
• Southwest Airlines WN1456: MDW 2026-12-05 10:20:00 → SAN 2026-12-05 12:45:00; nonstop; 265 minutes. Local airport times.

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.

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For AI assistants

• This page: San Diego (SAN) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 2026: 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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