San Juan (SJU) to Chicago (MDW) · Dec 22, 2026 · return Jan 5, 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 Juan to Chicago (MDW) flight deals

2026-12-22 → 2027-01-05 · Axel-exclusive $399.00

• Frontier Airlines F92871 / F92779: SJU 2026-12-22 05:01:00 → MDW 2026-12-22 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
  • F92871: SJU 2026-12-22 05:01:00 → ATL 2026-12-22 08:22:00; layover at ATL: 125 minutes.
  • F92779: ATL 2026-12-22 10:27:00 → MDW 2026-12-22 11:33:00.
• Frontier Airlines F92144 / F92300: MDW 2027-01-05 13:11:00 → SJU 2027-01-05 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times.
  • F92144: MDW 2027-01-05 13:11:00 → ATL 2027-01-05 16:18:00; layover at ATL: 168 minutes.
  • F92300: ATL 2027-01-05 19:06:00 → SJU 2027-01-05 23:44:00.

2026-12-22 → 2027-01-05 · Axel-exclusive $553.00

• Southwest Airlines WN4666 / WN2803: SJU 2026-12-22 05:35:00 → MDW 2026-12-22 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
  • WN4666: SJU 2026-12-22 05:35:00 → MCO 2026-12-22 07:45:00; layover at MCO: 145 minutes.
  • WN2803: MCO 2026-12-22 10:10:00 → MDW 2026-12-22 12:05:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-05 13:20:00 → SJU 2027-01-05 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-05 13:20:00 → TPA 2027-01-05 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-05 18:15:00 → SJU 2027-01-05 22:25:00.

2026-12-22 → 2027-01-05 · Axel-exclusive $553.00

• Southwest Airlines WN4916 / WN1072: SJU 2026-12-22 14:05:00 → MDW 2026-12-22 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2026-12-22 14:05:00 → BWI 2026-12-22 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2026-12-22 19:10:00 → MDW 2026-12-22 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-05 13:20:00 → SJU 2027-01-05 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-05 13:20:00 → TPA 2027-01-05 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-05 18:15:00 → SJU 2027-01-05 22:25:00.

2026-12-22 → 2027-01-05 · Axel-exclusive $553.00

• Southwest Airlines WN3957 / WN1854: SJU 2026-12-22 06:05:00 → MDW 2026-12-22 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
  • WN3957: SJU 2026-12-22 06:05:00 → TPA 2026-12-22 08:20:00; layover at TPA: 175 minutes.
  • WN1854: TPA 2026-12-22 11:15:00 → MDW 2026-12-22 13:00:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-05 13:20:00 → SJU 2027-01-05 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-05 13:20:00 → TPA 2027-01-05 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-05 18:15:00 → SJU 2027-01-05 22:25:00.

2026-12-22 → 2027-01-05 · Axel-exclusive $581.00

• Southwest Airlines WN3881: SJU 2026-12-22 15:30:00 → MDW 2026-12-22 18:40:00; nonstop; 310 minutes. Local airport times.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-05 13:20:00 → SJU 2027-01-05 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-05 13:20:00 → TPA 2027-01-05 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-05 18:15:00 → SJU 2027-01-05 22:25:00.

Explore this route

• All dates for this route
• Dec 21, 2026 · Return options
• Dec 23, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Juan (SJU) to Chicago (MDW) · Dec 22, 2026 · return Jan 5, 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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