Chicago to San Juan ๐ต๐ท
Cheapest fare
$96
Fastest
4h 42m
Direct from
$96
Dates tracked
15
Cheapest fare
$96
Wed, Jan 13 ยท Direct ยท 4h 46m ยท Frontier Airlines
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Price calendar
Cheapest round-trip fare by departure day Cheap Average Pricey
November 2026
Price trend
Price alert
Cheapest day to fly
Saturday
Averages $196, vs $290 on Mondays.
Work-hours calculator
This flight to San Juan costs you 6h 24m of work.
Same money as
1
SUV fuel tanks
5
large pizzas
7
cinema tickets
16
fancy coffees
Airlines on this route
Frontier Airlines
from $96 ยท 10 dates
Southwest Airlines
from $201 ยท 3 dates
United Airlines
from $251 ยท 1 dates
American Airlines
from $264 ยท 1 dates
Destination guide
Discover San Juan
About San Juan
San Juan ( san WHAHN, Spanish: [saล หxwan]; Spanish for "Saint John") is the capital city and most populous municipality in Puerto Rico, an unincorporated territory and insular area of the United States. San Juan was founded by Spanish colonists in 1521, who called it Ciudad de Puerto Rico (Spanish for "Rich Port City"). Puerto Rico's capital is the second oldest European-established capital city in the Americas, after Santo Domingo, in the Dominican Republic, founded in 1496, and is the oldest European-established city under United States sovereignty.
Text from Wikipedia โ San Juan, Puerto Rico, licensed CC BY-SA 4.0.
All dates
Every fare, by date
| Departs | Return | Airline | Stops | Price |
|---|---|---|---|---|
| Mon, Nov 23 | Wed, Dec 2 | Frontier Airlines | 1 stop | $202 |
| Wed, Nov 25 | Fri, Dec 4 | American Airlines | 1 stop | $264 |
| Fri, Dec 4 | Mon, Dec 14 | Frontier Airlines | 1 stop | $196 |
| Sat, Dec 5 | Sat, Dec 12 | Frontier Airlines | 1 stop | $196 |
| Fri, Dec 11 | Tue, Dec 15 | United Airlines |
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FAQ
Chicago to San Juan: answers
How much is a flight from Chicago to San Juan?+
The cheapest fare we see right now is $96 one way on Wed, Jan 13 with Frontier Airlines.
Are there direct flights from Chicago to San Juan?+
Yes โ direct fares start from $96.
How long is the flight from Chicago to San Juan?+
The fastest itinerary we track takes about 4h 42m door to door.
What is the cheapest day to fly to San Juan?+
Saturday departures are the cheapest on average right now, Monday the most expensive.
