Flight schedule from Chicago (CHI) to San Juan (Puerto Rico) (SJU)
Select a travel date in the flight schedule for the route from Chicago (CHI) to San Juan (Puerto Rico) (SJU) and compare affordable flight deals.
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- August 2 – 8, 2026
- August 9 – 15, 2026
- August 16 – 22, 2026
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Tips and tricks to help you find cheap flights from Chicago to San Juan (Puerto Rico)
Favorite airline: American Airlines
79 % of flights booked on the route from Chicago to San Juan (Puerto Rico) are booked with American Airlines, Spirit Airlines and United Airlines.
American Airlines
29 %
Spirit Airlines
27 %
United Airlines
23 %
Important flight information
Frequently Asked Questions (FAQ)
A nonstop flight from Chicago to San Juan (Puerto Rico) typically takes around 3 hours 49 minutes. This makes the nonstop service the fastest and most convenient way to travel between Chicago and San Juan (Puerto Rico). It is worth checking flight times when searching, as they can vary by airline and travel date.
Yes, there are nonstop flights from Chicago to San Juan (Puerto Rico), averaging around 6 to 7 flights per day, operated by, among others, United Airlines, American Airlines and NK. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Direct flights from Chicago to San Juan (Puerto Rico) are operated by, among others, United Airlines, American Airlines and NK. These flights take you to San Juan (Puerto Rico) nonstop, making them especially practical for short trips or weekend getaways. It is still worth comparing departure times and airline policies, as baggage rules and fees can vary.
Nonstop flights from Chicago to San Juan (Puerto Rico) operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
From Chicago to San Juan (Puerto Rico), there are on average around 6 to 7 flights per day. This usually means you have a good choice of departure times. If you are flexible, you can easily compare times, prices, and airlines.
From Chicago to San Juan (Puerto Rico), there are around 46 to 47 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
The earliest nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 7:30 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in San Juan (Puerto Rico).
The last nonstop flight from Chicago to San Juan (Puerto Rico) usually departs at 10:25 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.