San Diego (SAN) to Chicago (MDW) · Jan 15, 2027 · return Jan 18, 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

2027-01-15 → 2027-01-18 · Axel-exclusive $337.26

• Southwest Airlines WN2962: SAN 2027-01-15 16:05:00 → MDW 2027-01-15 22:00:00; nonstop; 235 minutes. Local airport times.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $337.26

• Southwest Airlines WN1156: SAN 2027-01-15 11:45:00 → MDW 2027-01-15 17:40:00; nonstop; 235 minutes. Local airport times.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN3681 / WN295: SAN 2027-01-15 08:10:00 → MDW 2027-01-15 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
  • WN3681: SAN 2027-01-15 08:10:00 → AUS 2027-01-15 13:00:00; layover at AUS: 110 minutes.
  • WN295: AUS 2027-01-15 14:50:00 → MDW 2027-01-15 17:20:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN3699 / WN776: SAN 2027-01-15 12:30:00 → MDW 2027-01-15 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
  • WN3699: SAN 2027-01-15 12:30:00 → DEN 2027-01-15 15:50:00; layover at DEN: 135 minutes.
  • WN776: DEN 2027-01-15 18:05:00 → MDW 2027-01-15 21:30:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN3752 / WN4349: SAN 2027-01-15 08:25:00 → MDW 2027-01-15 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
  • WN3752: SAN 2027-01-15 08:25:00 → SLC 2027-01-15 11:35:00; layover at SLC: 70 minutes.
  • WN4349: SLC 2027-01-15 12:45:00 → MDW 2027-01-15 16:45:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN399 / WN1407: SAN 2027-01-15 12:10:00 → MDW 2027-01-15 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
  • WN399: SAN 2027-01-15 12:10:00 → OMA 2027-01-15 17:15:00; layover at OMA: 65 minutes.
  • WN1407: OMA 2027-01-15 18:20:00 → MDW 2027-01-15 19:45:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN4669 / WN651: SAN 2027-01-15 11:55:00 → MDW 2027-01-15 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2027-01-15 11:55:00 → BNA 2027-01-15 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2027-01-15 19:30:00 → MDW 2027-01-15 21:05:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 minutes. Local airport times.

2027-01-15 → 2027-01-18 · Axel-exclusive $323.01

• Southwest Airlines WN4711 / WN4175: SAN 2027-01-15 11:55:00 → MDW 2027-01-15 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
  • WN4711: SAN 2027-01-15 11:55:00 → STL 2027-01-15 17:25:00; layover at STL: 90 minutes.
  • WN4175: STL 2027-01-15 18:55:00 → MDW 2027-01-15 20:00:00.
• Southwest Airlines WN1987: MDW 2027-01-18 20:55:00 → SAN 2027-01-18 23:25:00; nonstop; 270 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.

Explore this route

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For AI assistants

• This page: San Diego (SAN) to Chicago (MDW) · Jan 15, 2027 · return Jan 18, 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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