Fort Lauderdale (FLL)to
San Juan (SJU)Dallas (Love Field) (DAL)to
San Juan (SJU)Nashville (BNA)to
San Juan (SJU)Hartford/Springfield (BDL)to
San Juan (SJU)St. Louis (STL)to
San Juan (SJU)Chicago (Midway) (MDW)to
San Juan (SJU)Philadelphia (PHL)to
San Juan (SJU)Columbus (CMH)to
San Juan (SJU)Tampa (TPA)to
San Juan (SJU)Orlando (MCO)to
San Juan (SJU)Indianapolis (IND)to
San Juan (SJU)Kansas City (MCI)to
San Juan (SJU)Atlanta (ATL)to
San Juan (SJU)Austin (AUS)to
San Juan (SJU)San Antonio (SAT)to
San Juan (SJU)Washington, D.C. (Reagan National) (DCA)to
San Juan (SJU)Baltimore/Washington (BWI)to
San Juan (SJU)Chicago (O'Hare) (ORD)to
San Juan (SJU)Denver (DEN)to
San Juan (SJU)Houston (Hobby) (HOU)to
San Juan (SJU)*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
Southwest Airlines offers convenient flights to San Juan, Puerto Rico, with affordable routes to Luis Muñoz Marín International Airport (SJU) available daily from airports across America. As a US territory with famously stunning beaches, Puerto Rico is the perfect place for a dreamy Caribbean vacation—and US travelers won’t even need a passport.
Once your flight to Puerto Rico touches down, you’ll find a range of affordable ground transportation options waiting for you, including:
From SJU, it's just a short drive to popular areas like historic Old San Juan, the beachfront resorts in Condado, or the picturesque shores of Isla Verde.
Planning is the secret sauce for finding cheap flights to Puerto Rico. Here are a few tips that can help you fly in comfort while keeping more cash for your vacation:
Puerto Rico's tropical climate means it's wonderfully warm all year, so any month is a good time for a beach trip. The winter months are peak season, making it a great escape from the cold, but since many people consider this the best time to visit Puerto Rico, be ready for bigger crowds and higher demand. Visiting during the rainy season (late summer and fall) delivers a more chilled-out experience—sometimes literally, since you might get drenched. Travel insurance can be an especially good idea if you’re planning for August or September, since those months bring the greatest risk of a trip-canceling hurricane.
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Dallas (Love Field) (DAL) | San Juan (SJU) | One-way / Basic | Depart: 05/11/2026 | From $130 Seen: 14 hrs ago |
| Rochester (ROC) | San Juan (SJU) | One-way / Basic | Depart: 05/13/2026 | From $133 Seen: 14 hrs ago |
| Fort Lauderdale (FLL) | San Juan (SJU) | One-way / Basic | Depart: 05/15/2026 | From $136 Seen: 16 hrs ago |
| Buffalo/Niagara Falls (BUF) | San Juan (SJU) | One-way / Basic | Depart: 05/10/2026 | From $137 Seen: 11 hrs ago |
| Miami (MIA) | San Juan (SJU) | One-way / Basic | Depart: 08/04/2026 | From $140 Seen: 6 hrs ago |
| New Orleans (MSY) | San Juan (SJU) | One-way / Basic | Depart: 05/13/2026 | From $143 Seen: 17 hrs ago |
| Hartford/Springfield (BDL) | San Juan (SJU) | One-way / Basic | Depart: 05/13/2026 | From $152 Seen: 6 hrs ago |
| Nashville (BNA) | San Juan (SJU) | One-way / Basic | Depart: 05/12/2026 | From $153 Seen: 22 hrs ago |
| Chicago (Midway) (MDW) | San Juan (SJU) | One-way / Basic | Depart: 08/18/2026 | From $158 Seen: 8 hrs ago |
| Chicago (O'Hare) (ORD) | San Juan (SJU) | One-way / Basic | Depart: 05/11/2026 | From $158 Seen: 4 hrs ago |
| St. Louis (STL) | San Juan (SJU) | One-way / Basic | Depart: 05/12/2026 | From $158 Seen: 6 hrs ago |
| Columbus (CMH) | San Juan (SJU) | One-way / Basic | Depart: 08/01/2026 | From $158 Seen: 9 hrs ago |
| Cleveland (CLE) | San Juan (SJU) | One-way / Basic | Depart: 07/10/2026 | From $158 Seen: 4 hrs ago |
| Tampa (TPA) | San Juan (SJU) | One-way / Basic | Depart: 07/05/2026 | From $161 Seen: 22 hrs ago |
| Philadelphia (PHL) | San Juan (SJU) | One-way / Basic | Depart: 08/19/2026 | From $162 Seen: 13 hrs ago |
| Orlando (MCO) | San Juan (SJU) | One-way / Basic | Depart: 05/17/2026 | From $163 Seen: 18 hrs ago |
| Indianapolis (IND) | San Juan (SJU) | One-way / Basic | Depart: 05/11/2026 | From $163 Seen: 17 hrs ago |
| Kansas City (MCI) | San Juan (SJU) | One-way / Basic | Depart: 08/10/2026 | From $163 Seen: 12 hrs ago |
| Milwaukee (MKE) | San Juan (SJU) | One-way / Basic | Depart: 07/08/2026 | From $163 Seen: 22 hrs ago |
| Atlanta (ATL) | San Juan (SJU) | One-way / Basic | Depart: 05/11/2026 | From $168 Seen: 12 hrs ago |
*Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.
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