Frontier AirlinesDepart00:17
Wed, Jan 13ORD → SJU
4h 46m · Direct
$86one way, per person
View deal
- Cheapest fare
- $86
- Cheapest month
- January
- Direct flights
- Yes
- Flight time
- 4h 46m
Frontier Airlines · Wed, Jan 13
from $86
Frontier Airlines
3,300 km
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Cheapest month to fly from Chicago to San Juan
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in January 2027
The lowest fares we've seen for each day, cheapest first.
See every date in January 2027 →Plan the rest of your trip to San Juan
Where to stay, what to do and getting around, from our travel partners.
About flights from Chicago to San Juan
Chicago (CHI) and San Juan (SJU) are about 3,300 km apart. Direct flights take around 4h 46m, and recent direct fares were with Frontier Airlines. Over the next few months, one-way fares start from $86, and January 2027 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Chicago to San Juan?
The cheapest one-way fare we've seen recently is $86 with Frontier Airlines, departing Wednesday, January 13, 2027. Over the coming months, the lowest fare in each month ranges from $86 to $246.
What is the cheapest month to fly from Chicago to San Juan?
January 2027 currently has the lowest fares, from $86 one way.
Are there direct flights from Chicago to San Juan?
Yes. Recent direct fares were with Frontier Airlines.
How long is the flight from Chicago to San Juan?
A direct flight takes about 4h 46m. Chicago and San Juan are around 3,300 km apart.
Which airlines fly from Chicago to San Juan?
Recent fares on this route were with Frontier Airlines.
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