San Juan (SJU) to Chicago (MDW) · Jan 13, 2027 · return Jan 27, 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

2027-01-13 → 2027-01-27 · Axel-exclusive $285.00

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

2027-01-13 → 2027-01-27 · Axel-exclusive $395.00

• Southwest Airlines WN3957 / WN1854: SJU 2027-01-13 06:05:00 → MDW 2027-01-13 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
  • WN3957: SJU 2027-01-13 06:05:00 → TPA 2027-01-13 08:20:00; layover at TPA: 175 minutes.
  • WN1854: TPA 2027-01-13 11:15:00 → MDW 2027-01-13 13:00:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-27 13:20:00 → SJU 2027-01-27 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-27 13:20:00 → TPA 2027-01-27 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-27 18:15:00 → SJU 2027-01-27 22:25:00.

2027-01-13 → 2027-01-27 · Axel-exclusive $395.00

• Southwest Airlines WN4916 / WN1072: SJU 2027-01-13 14:05:00 → MDW 2027-01-13 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
  • WN4916: SJU 2027-01-13 14:05:00 → BWI 2027-01-13 17:10:00; layover at BWI: 120 minutes.
  • WN1072: BWI 2027-01-13 19:10:00 → MDW 2027-01-13 20:15:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-27 13:20:00 → SJU 2027-01-27 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-27 13:20:00 → TPA 2027-01-27 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-27 18:15:00 → SJU 2027-01-27 22:25:00.

2027-01-13 → 2027-01-27 · Axel-exclusive $395.00

• Southwest Airlines WN4666 / WN2803: SJU 2027-01-13 05:35:00 → MDW 2027-01-13 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
  • WN4666: SJU 2027-01-13 05:35:00 → MCO 2027-01-13 07:45:00; layover at MCO: 145 minutes.
  • WN2803: MCO 2027-01-13 10:10:00 → MDW 2027-01-13 12:05:00.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-27 13:20:00 → SJU 2027-01-27 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-27 13:20:00 → TPA 2027-01-27 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-27 18:15:00 → SJU 2027-01-27 22:25:00.

2027-01-13 → 2027-01-27 · Axel-exclusive $415.00

• Southwest Airlines WN3881: SJU 2027-01-13 15:30:00 → MDW 2027-01-13 18:40:00; nonstop; 310 minutes. Local airport times.
• Southwest Airlines WN3048 / WN3363: MDW 2027-01-27 13:20:00 → SJU 2027-01-27 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times.
  • WN3048: MDW 2027-01-27 13:20:00 → TPA 2027-01-27 16:55:00; layover at TPA: 80 minutes.
  • WN3363: TPA 2027-01-27 18:15:00 → SJU 2027-01-27 22:25:00.

Explore this route

• All dates for this route
• Jan 12, 2027 · Return options
• Jan 14, 2027 · Return options
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For AI assistants

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