- Cheapest roundtrip flight
- from€333
- Fastest flight
- non-stop flights
- 20x / week
- Flight distance
- 3,341 km
- Time difference
- Most popular airlines
- United Airlines
- American Airlines
- Frontier Airlines
- United Airlines
Cheap flight offers from Chicago O'Hare to San Juan Puerto Rico
sorted by price and recency
- – –ORD–SJUnon-stop flight–SJU–ORD1 stopover€1,006
- – –ORD–SJU1 stopover–SJU–ORD1 stopover€503
- – –ORD–SJUnon-stop flight–SJU–ORD1 stopover€499
- – –ORD–SJUnon-stop flight–SJU–ORD1 stopover€400
- – –ORD–SJU1 stopover–SJU–ORD1 stopover€333
Flight schedule from Chicago O'Hare (ORD) to San Juan (Puerto Rico) (SJU)
Select a travel date in the flight schedule for the route from Chicago O'Hare (ORD) to San Juan (Puerto Rico) (SJU) and compare affordable flight deals.
offers
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Matching outbound flightsORD–SJU · 5 of 5
fromto
dep.arr.
durationstopovers
- November 8 – 14, 2026
- November 15 – 21, 2026
- November 22 – 28, 2026
- ORDSJUnonstop
- ORDSJUnonstop
- ORDSJUnonstop
- ORDSJUnonstop
- ORDSJUnonstop
Important flight information
Frequently Asked Questions (FAQ)
How long is the flight from Chicago O'Hare to San Juan (Puerto Rico)?
A nonstop flight from Chicago O'Hare to San Juan (Puerto Rico) typically takes around 4 hours 47 minutes. If you choose a connecting flight, allow more travel time. Typical one-stop itineraries take around 8 hours 54 minutes. For the quickest trip, a nonstop flight is usually the most comfortable choice.
Are there nonstop flights from Chicago O'Hare to San Juan (Puerto Rico)?
Yes, there are nonstop flights from Chicago O'Hare to San Juan (Puerto Rico), averaging around 2 to 3 flights per day, operated by, among others, American Airlines, United Airlines and Frontier Airlines. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Which airlines fly from Chicago O'Hare to San Juan (Puerto Rico)?
Direct flights from Chicago O'Hare to San Juan (Puerto Rico) are operated by, among others, American Airlines, United Airlines and Frontier Airlines. Connecting flights with one stop are also available, for example with JetBlue Airways (via Fort Lauderdale, Boston), United Airlines (via Washington DC) and American Airlines (via Charlotte). If travel time matters to you, a direct flight is usually the most convenient option. Connecting flights often give you more choice of departure times and airlines.
On which days are there nonstop flights from Chicago O'Hare to San Juan (Puerto Rico)?
Nonstop flights from Chicago O'Hare 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.
How many flights are there per day from Chicago O'Hare to San Juan (Puerto Rico)?
On the route from Chicago O'Hare to San Juan (Puerto Rico), there are on average around 2 to 3 flights per day. The number of flights can vary by day of the week and season. If you are flexible with your dates, it is worth comparing several departure days.
How many flights per week are there from Chicago O'Hare to San Juan (Puerto Rico)?
On the route from Chicago O'Hare to San Juan (Puerto Rico), there are around 20 to 21 flights per week. The number of flights can vary depending on the season and day of the week. If you have flexibility, it is worth looking at several departure days.
When does the first flight from Chicago O'Hare to San Juan (Puerto Rico) depart?
The earliest nonstop flight from Chicago O'Hare to San Juan (Puerto Rico) usually departs at 12:17 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).
When does the last flight from Chicago O'Hare to San Juan (Puerto Rico) depart?
The last nonstop flight from Chicago O'Hare to San Juan (Puerto Rico) usually departs at 11:53 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.