Chicago (MDW) to San Diego (SAN) · Jan 24, 2027 · return Jan 31, 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

2027-01-24 → 2027-01-31 · Axel-exclusive $332.50

• Southwest Airlines WN1987: MDW 2027-01-24 21:15:00 → SAN 2027-01-24 23:55:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $332.50

• Southwest Airlines WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; nonstop; 260 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN725 / WN1079: MDW 2027-01-24 09:55:00 → SAN 2027-01-24 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
  • WN725: MDW 2027-01-24 09:55:00 → BNA 2027-01-24 11:30:00; layover at BNA: 60 minutes.
  • WN1079: BNA 2027-01-24 12:30:00 → SAN 2027-01-24 14:55:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN1354 / WN225: MDW 2027-01-24 13:20:00 → SAN 2027-01-24 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-24 13:20:00 → CMH 2027-01-24 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-24 16:45:00 → SAN 2027-01-24 18:35:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN2995 / WN2447: MDW 2027-01-24 05:05:00 → SAN 2027-01-24 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
  • WN2995: MDW 2027-01-24 05:05:00 → PHX 2027-01-24 07:55:00; layover at PHX: 85 minutes.
  • WN2447: PHX 2027-01-24 09:20:00 → SAN 2027-01-24 09:40:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN4606 / WN1780: MDW 2027-01-24 14:35:00 → SAN 2027-01-24 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN4606: MDW 2027-01-24 14:35:00 → DEN 2027-01-24 16:15:00; layover at DEN: 70 minutes.
  • WN1780: DEN 2027-01-24 17:25:00 → SAN 2027-01-24 18:45:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN153 / WN167: MDW 2027-01-24 15:45:00 → SAN 2027-01-24 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
  • WN153: MDW 2027-01-24 15:45:00 → ABQ 2027-01-24 17:55:00; layover at ABQ: 115 minutes.
  • WN167: ABQ 2027-01-24 19:50:00 → SAN 2027-01-24 20:50:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $318.25

• Southwest Airlines WN4395 / WN3167: MDW 2027-01-24 10:15:00 → SAN 2027-01-24 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
  • WN4395: MDW 2027-01-24 10:15:00 → HOU 2027-01-24 12:50:00; layover at HOU: 95 minutes.
  • WN3167: HOU 2027-01-24 14:25:00 → SAN 2027-01-24 15:50:00.
• Southwest Airlines WN1981: SAN 2027-01-31 12:00:00 → MDW 2027-01-31 17:55:00; nonstop; 235 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: Chicago (MDW) to San Diego (SAN) · Jan 24, 2027 · return Jan 31, 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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