Last updated on 05-29-2026 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes . Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.
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Which airlines fly from Chicago to San Juan?
Chicago to San Juan Flight Route Information
- Flight Duration: Approximately 4 hours 45 minutes nonstop
- Distance: About 2,070 miles (3,331 km)
- Frequent Departures: Nonstop and connecting flights available daily
Information about airports from Chicago to San Juan
O’Hare International Airport (ORD) is one of the busiest airports in the U.S., offering nonstop service to top Caribbean destinations. On the other end, Luis Muñoz Marín International Airport (SJU) is Puerto Rico’s main gateway, located near San Juan’s historic Old Town, beaches, and resorts.
Popular Flight Routes from Chicago (ORD):
- Chicago to Cancún (CUN)
- Chicago to Punta Cana (PUJ)
- Chicago to Aruba (AUA)
- Chicago to Montego Bay (MBJ)
- Chicago to Nassau (NAS)
Popular Flight Routes to San Juan (SJU):
- Newark (EWR) to San Juan
- New York (JFK) to San Juan
- Orlando (MCO) to San Juan
- Boston (BOS) to San Juan
- Philadelphia (PHL) to San Juan
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Frequently Asked Questions about flight from Chicago to San Juan
How many airports in Chicago?
Chicago is served by two main airports — O’Hare International Airport (ORD) and Midway International Airport (MDW). Most international and long-haul flights to San Juan depart from O’Hare.
How long is the flight from Chicago to San Juan?
The flight duration from Chicago to San Juan is approximately 4 hours and 45 minutes nonstop.
Which is the best airline to fly from Chicago to San Juan?
Top airlines for this route include United Airlines, American Airlines, and Frontier Airlines, offering both nonstop and connecting flights from Chicago to San Juan.
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