Flights from Chicago to San Juan
The lowest fare Aviasales travellers found for every month, with the airline and stops. Pick a month to open that flight, or search your own dates. Results stay here on 365Vistas.
Chicago to San Juan fares by month
Lowest one-way fare per month that Aviasales travellers found (as of Oct 31). Fares change daily; tap a month to see that flight's live price.
| Month | From | Date | Airline | Stops | |
|---|---|---|---|---|---|
| November 2026 | $132 | Nov 11 | Frontier | 1 stop | See flight › |
| January 2027 | $86 | Jan 13 | Frontier | Direct | See flight › |
In San Juan
Plan a trip to San Juan, Puerto Rico: the best time to go, getting around, top things to do from Old San Juan to El Yunque and the bioluminescent bays.
Chicago to San Juan flight FAQ
What is the lowest fare from Chicago to San Juan?
The lowest one-way fare Aviasales travellers found was $86 for a flight on Jan 13 (January 2027) with Frontier, direct. Fares change daily; search your dates for today's live price.
Which month has the lowest fares from Chicago to San Juan?
In the fares found as of Oct 31, January 2027 had the lowest price ($86). The table above lists the lowest fare found for every month.
Which airlines fly from Chicago to San Juan?
In the lowest fares found for this route: Frontier. More airlines show up when you search your exact dates.
Are there direct flights from Chicago to San Juan?
Yes. Some of the lowest fares found for this route are direct flights (marked "Direct" in the table).
How long is the flight from Chicago to San Juan?
The quickest of the lowest fares found takes 4 h 46 min (direct, Frontier). Direct flights, when available, are shorter.