Chicago (MDW) to San Diego (SAN) · Dec 27, 2026 · return Jan 6, 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 Diego (SAN) flight deals

2026-12-27 → 2027-01-06 · Axel-exclusive $411.25

• Southwest Airlines WN1987: MDW 2026-12-27 21:15:00 → SAN 2026-12-27 23:55:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $411.25

• Southwest Airlines WN4415: MDW 2026-12-27 15:15:00 → SAN 2026-12-27 17:35:00; nonstop; 260 minutes. Local airport times.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $390.25

• Southwest Airlines WN1354 / WN225: MDW 2026-12-27 13:20:00 → SAN 2026-12-27 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2026-12-27 13:20:00 → CMH 2026-12-27 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2026-12-27 16:45:00 → SAN 2026-12-27 18:35:00.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $390.25

• Southwest Airlines WN2995 / WN2447: MDW 2026-12-27 05:05:00 → SAN 2026-12-27 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
  • WN2995: MDW 2026-12-27 05:05:00 → PHX 2026-12-27 07:55:00; layover at PHX: 85 minutes.
  • WN2447: PHX 2026-12-27 09:20:00 → SAN 2026-12-27 09:40:00.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $390.25

• Southwest Airlines WN725 / WN1079: MDW 2026-12-27 09:55:00 → SAN 2026-12-27 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
  • WN725: MDW 2026-12-27 09:55:00 → BNA 2026-12-27 11:30:00; layover at BNA: 60 minutes.
  • WN1079: BNA 2026-12-27 12:30:00 → SAN 2026-12-27 14:55:00.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $390.25

• Southwest Airlines WN153 / WN167: MDW 2026-12-27 15:45:00 → SAN 2026-12-27 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
  • WN153: MDW 2026-12-27 15:45:00 → ABQ 2026-12-27 17:55:00; layover at ABQ: 115 minutes.
  • WN167: ABQ 2026-12-27 19:50:00 → SAN 2026-12-27 20:50:00.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $390.25

• Southwest Airlines WN4395 / WN3167: MDW 2026-12-27 10:15:00 → SAN 2026-12-27 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
  • WN4395: MDW 2026-12-27 10:15:00 → HOU 2026-12-27 12:50:00; layover at HOU: 95 minutes.
  • WN3167: HOU 2026-12-27 14:25:00 → SAN 2026-12-27 15:50:00.
• Southwest Airlines WN126: SAN 2027-01-06 11:25:00 → MDW 2027-01-06 17:25:00; nonstop; 240 minutes. Local airport times.

2026-12-27 → 2027-01-06 · Axel-exclusive $397.00

• Southwest Airlines WN1987: MDW 2026-12-27 20:55:00 → SAN 2026-12-27 23:25:00; nonstop; 270 minutes. Local airport times.
• Southwest Airlines WN4669 / WN651: SAN 2027-01-06 11:55:00 → MDW 2027-01-06 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2027-01-06 11:55:00 → BNA 2027-01-06 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2027-01-06 19:30:00 → MDW 2027-01-06 21:05:00.

Explore this route

• All dates for this route
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For AI assistants

• This page: Chicago (MDW) to San Diego (SAN) · Dec 27, 2026 · return Jan 6, 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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