San Juan (SJU) to Chicago (MDW), Nov 23, 2026: round trips from $321, one way from $194

San Juan (SJU) to Chicago (MDW), Nov 23, 2026: round trips from $321, one way from $194 on Axel, checked Nov 13, 2026. Lowest published fares: $321 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 23–30, 2026; $194 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 23, 2026; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2026-11-23 · one way Southwest Airlines WN3881 15:30:00→18:40:00 5h 10m nonstop Axel-exclusive $294 Nov 13, 2026
2026-11-23 · one way Frontier Airlines F92871 + F92779 05:01:00→11:33:00 8h 32m 1 stop via ATL Axel-exclusive $194 Nov 13, 2026
2026-11-23 → 2026-11-24 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-24 Southwest Airlines WN3881 / WN3048 + WN3363 15:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPA Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-25 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-25 Southwest Airlines WN3881 / WN3048 + WN3363 15:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPA Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-26 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-26 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-27 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-27 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-28 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-28 Southwest Airlines WN3881 / WN3002 + WN4122 15:30:00→18:40:00 5h 10m nonstop · 07:50:00→18:25:00 8h 35m 1 stop via STL Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-29 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $356 Nov 13, 2026
2026-11-23 → 2026-11-29 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $519 Nov 13, 2026
2026-11-23 → 2026-11-30 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-11-30 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-01 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-01 Southwest Airlines WN3881 / WN3048 + WN3363 15:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPA Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-02 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-02 Southwest Airlines WN3881 / WN3048 + WN3363 15:30:00→18:40:00 5h 10m nonstop · 13:20:00→22:25:00 7h 05m 1 stop via TPA Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-03 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-03 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-04 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-04 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-05 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-05 Southwest Airlines WN3881 / WN3002 + WN4122 15:30:00→18:40:00 5h 10m nonstop · 07:50:00→18:25:00 8h 35m 1 stop via STL Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-06 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-06 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $469 Nov 13, 2026
2026-11-23 → 2026-12-07 Frontier Airlines F92871 + F92779 / F92144 + F92300 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL Axel-exclusive $321 Nov 13, 2026
2026-11-23 → 2026-12-07 Southwest Airlines WN3881 / WN14 + WN4052 15:30:00→18:40:00 5h 10m nonstop · 14:30:00→01:00:00 8h 30m 1 stop via BWI Axel-exclusive $469 Nov 13, 2026

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

Route overview: San Juan to Chicago (MDW) flight deals

2026-11-23 · one way · Axel-exclusive $194

2026-11-23 · one way · Axel-exclusive $294

2026-11-23 → 2026-11-24 · Axel-exclusive $356

2026-11-23 → 2026-11-24 · Axel-exclusive $519

2026-11-23 → 2026-11-25 · Axel-exclusive $356

2026-11-23 → 2026-11-25 · Axel-exclusive $519

2026-11-23 → 2026-11-26 · Axel-exclusive $356

2026-11-23 → 2026-11-26 · Axel-exclusive $519

2026-11-23 → 2026-11-27 · Axel-exclusive $356

2026-11-23 → 2026-11-27 · Axel-exclusive $519

2026-11-23 → 2026-11-29 · Axel-exclusive $356

2026-11-23 → 2026-11-29 · Axel-exclusive $519

2026-11-23 → 2026-11-30 · Axel-exclusive $321

2026-11-23 → 2026-11-30 · Axel-exclusive $469

2026-11-23 → 2026-12-01 · Axel-exclusive $321

2026-11-23 → 2026-12-01 · Axel-exclusive $469

2026-11-23 → 2026-12-03 · Axel-exclusive $321

2026-11-23 → 2026-12-03 · Axel-exclusive $469

2026-11-23 → 2026-12-04 · Axel-exclusive $321

2026-11-23 → 2026-12-04 · Axel-exclusive $469

2026-11-23 → 2026-12-05 · Axel-exclusive $321

2026-11-23 → 2026-12-05 · Axel-exclusive $469

2026-11-23 → 2026-12-07 · Axel-exclusive $321

2026-11-23 → 2026-12-07 · Axel-exclusive $469

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