San Diego (SAN) to Chicago (MDW), Jan 1–3, 2027: from $226 one way

San Diego (SAN) to Chicago (MDW), Jan 1–3, 2027: from $226 one way on Axel, checked Oct 29, 2026. Lowest published fare: $226 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 1, 2027, 1 adult, economy, checked Oct 29, 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

2027-01-02 · one way · Axel-exclusive $246.05

• Southwest Airlines WN634: SAN 2027-01-02 08:15:00 → MDW 2027-01-02 14:15:00; nonstop; 240 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $246.05

• Southwest Airlines WN1011: SAN 2027-01-03 22:40:00 → MDW 2027-01-04 04:25:00; nonstop; 225 minutes. Local airport times.

2027-01-01 · one way · Axel-exclusive $246.05

• Southwest Airlines WN1156: SAN 2027-01-01 11:45:00 → MDW 2027-01-01 17:40:00; nonstop; 235 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $246.05

• Southwest Airlines WN1981: SAN 2027-01-03 12:00:00 → MDW 2027-01-03 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-02 · one way · Axel-exclusive $246.05

• Southwest Airlines WN2962: SAN 2027-01-02 16:05:00 → MDW 2027-01-02 22:00:00; nonstop; 235 minutes. Local airport times.

2027-01-01 · one way · Axel-exclusive $246.05

• Southwest Airlines WN2962: SAN 2027-01-01 16:05:00 → MDW 2027-01-01 22:00:00; nonstop; 235 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN4669 / WN651: SAN 2027-01-03 11:55:00 → MDW 2027-01-03 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2027-01-03 11:55:00 → BNA 2027-01-03 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2027-01-03 19:30:00 → MDW 2027-01-03 21:05:00.

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN3681 / WN295: SAN 2027-01-03 08:10:00 → MDW 2027-01-03 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
  • WN3681: SAN 2027-01-03 08:10:00 → AUS 2027-01-03 13:00:00; layover at AUS: 110 minutes.
  • WN295: AUS 2027-01-03 14:50:00 → MDW 2027-01-03 17:20:00.

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-02 · one way · Axel-exclusive $226.10

• 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.

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN4711 / WN4175: SAN 2027-01-03 11:55:00 → MDW 2027-01-03 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
  • WN4711: SAN 2027-01-03 11:55:00 → STL 2027-01-03 17:25:00; layover at STL: 90 minutes.
  • WN4175: STL 2027-01-03 18:55:00 → MDW 2027-01-03 20:00:00.

2027-01-02 · one way · Axel-exclusive $226.10

• 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.

2027-01-02 · one way · Axel-exclusive $226.10

• 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.

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN3752 / WN4349: SAN 2027-01-03 08:25:00 → MDW 2027-01-03 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
  • WN3752: SAN 2027-01-03 08:25:00 → SLC 2027-01-03 11:35:00; layover at SLC: 70 minutes.
  • WN4349: SLC 2027-01-03 12:45:00 → MDW 2027-01-03 16:45:00.

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN399 / WN1407: SAN 2027-01-03 12:10:00 → MDW 2027-01-03 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
  • WN399: SAN 2027-01-03 12:10:00 → OMA 2027-01-03 17:15:00; layover at OMA: 65 minutes.
  • WN1407: OMA 2027-01-03 18:20:00 → MDW 2027-01-03 19:45:00.

2027-01-03 · one way · Axel-exclusive $226.10

• Southwest Airlines WN3699 / WN776: SAN 2027-01-03 12:30:00 → MDW 2027-01-03 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
  • WN3699: SAN 2027-01-03 12:30:00 → DEN 2027-01-03 15:50:00; layover at DEN: 135 minutes.
  • WN776: DEN 2027-01-03 18:05:00 → MDW 2027-01-03 21:30:00.

2027-01-02 · one way · Axel-exclusive $226.10

• 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.

2027-01-02 · one way · Axel-exclusive $226.10

• Southwest Airlines WN3752 / WN4349: SAN 2027-01-02 08:25:00 → MDW 2027-01-02 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
  • WN3752: SAN 2027-01-02 08:25:00 → SLC 2027-01-02 11:35:00; layover at SLC: 70 minutes.
  • WN4349: SLC 2027-01-02 12:45:00 → MDW 2027-01-02 16:45:00.

2027-01-01 · one way · Axel-exclusive $226.10

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

2027-01-02 · one way · Axel-exclusive $226.10

• 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.

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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