San Juan (SJU) to Chicago (MDW), Nov 14, 2026: from $155 one way
San Juan (SJU) to Chicago (MDW), Nov 14, 2026: from $155 one way on Axel, checked Oct 29, 2026. Lowest published fare: $155 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 14, 2026, 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2026-11-14 · one way | Southwest Airlines | WN3881 | 15:30:00→18:40:00 5h 10m nonstop | Axel-exclusive $235.00 | 2026-10-29T01:23:44Z |
| 2026-11-14 · one way | Frontier Airlines | F92871 + F92779 | 05:01:00→11:33:00 8h 32m 1 stop via ATL | Axel-exclusive $155.00 | 2026-10-29T01:23:44Z |
| 2026-11-14 · one way | Southwest Airlines | WN4666 + WN2803 | 05:35:00→12:05:00 8h 30m 1 stop via MCO | Axel-exclusive $215.00 | 2026-10-29T01:23:44Z |
| 2026-11-14 · one way | Southwest Airlines | WN3957 + WN1854 | 06:05:00→13:00:00 8h 55m 1 stop via TPA | Axel-exclusive $215.00 | 2026-10-29T01:23:44Z |
| 2026-11-14 · one way | Southwest Airlines | WN4916 + WN1072 | 14:05:00→20:15:00 8h 10m 1 stop via BWI | Axel-exclusive $215.00 | 2026-10-29T01:23:44Z |
Route overview: San Juan to Chicago (MDW) flight deals
2026-11-14 · one way · Axel-exclusive $235.00
- Southwest Airlines WN3881: SJU 2026-11-14 15:30:00 → MDW 2026-11-14 18:40:00; nonstop; 310 minutes. Local airport times.
2026-11-14 · one way · Axel-exclusive $155.00
- Frontier Airlines F92871 / F92779: SJU 2026-11-14 05:01:00 → MDW 2026-11-14 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times.
- F92871: SJU 2026-11-14 05:01:00 → ATL 2026-11-14 08:22:00; layover at ATL: 125 minutes.
- F92779: ATL 2026-11-14 10:27:00 → MDW 2026-11-14 11:33:00.
2026-11-14 · one way · Axel-exclusive $215.00
- Southwest Airlines WN4666 / WN2803: SJU 2026-11-14 05:35:00 → MDW 2026-11-14 12:05:00; 1 stop(s) via MCO; 510 minutes. Local airport times.
- WN4666: SJU 2026-11-14 05:35:00 → MCO 2026-11-14 07:45:00; layover at MCO: 145 minutes.
- WN2803: MCO 2026-11-14 10:10:00 → MDW 2026-11-14 12:05:00.
2026-11-14 · one way · Axel-exclusive $215.00
- Southwest Airlines WN3957 / WN1854: SJU 2026-11-14 06:05:00 → MDW 2026-11-14 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times.
- WN3957: SJU 2026-11-14 06:05:00 → TPA 2026-11-14 08:20:00; layover at TPA: 175 minutes.
- WN1854: TPA 2026-11-14 11:15:00 → MDW 2026-11-14 13:00:00.
2026-11-14 · one way · Axel-exclusive $215.00
- Southwest Airlines WN4916 / WN1072: SJU 2026-11-14 14:05:00 → MDW 2026-11-14 20:15:00; 1 stop(s) via BWI; 490 minutes. Local airport times.
- WN4916: SJU 2026-11-14 14:05:00 → BWI 2026-11-14 17:10:00; layover at BWI: 120 minutes.
- WN1072: BWI 2026-11-14 19:10:00 → MDW 2026-11-14 20:15:00.
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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