Chicago → San Juan flights
Chicago (CGX, DPA, MDW, ORD, PWK, RFD)→San Juan (SIG, SJU)
from$227
Last observed price · Last checked: 11 Aug 2026 · Price may change
Selected search
Last checked: 11 Aug 2026 · Price may change
$227
Sun 13 Sep 2026 → Thu 17 Sep 2026
Frontier Airlines1 stop4 nights
CheapestLast checked: 11 Aug 2026 · Price may change
$227 lowest$300 average7h fastest
Tickets found in the last 7 days
The lowest fares our queries caught, cheapest first.
FA$227Cheapest13 Sep 2026 → 17 Sep 2026Frontier Airlines · 1 stop · 06:25Last checked: 11 Aug 2026 · Price may change4 nightsView ticket →JE$30118 Sep 2026 → 22 Sep 2026JetBlue · 2 stops · 06:00Last checked: 11 Aug 2026 · Price may change4 nightsView ticket →JE$31021 Oct 2026 → 25 Oct 2026JetBlue · 1 stop · 14:35Last checked: 11 Aug 2026 · Price may change4 nightsView ticket →FA$31522 Aug 2026 → 25 Aug 2026Frontier Airlines · 1 stop · 00:44Last checked: 11 Aug 2026 · Price may change3 nightsView ticket →G4$3442 Nov 2026 → 7 Nov 2026G4 · 1 stop · 17:55Last checked: 11 Aug 2026 · Price may change5 nightsView ticket →
Starting prices by month
The lowest fare our queries observed in each month. Open a month to see its days; click a day with no price and we will search it for you.
Observed priceLowest monthno price observedLast checked: 11 Aug 2026
Chicago → San JuanSun 13 Sep 2026 · $227
Find flightsRoute facts
Direct flights
Non-stop
CGX - SIG, 7h
Airlines seen
3
JetBlue, Frontier Airlines, G4
Cheapest month
November 2026
$186
Average observed
$300
Typical duration
7h
Alternative airports
6
DPA, MDW, ORD, PWK, RFD, SJU
Frequently asked
Are there direct flights from Chicago to San Juan?+−
Yes. We have seen non-stop flights on this route, flown by American Airlines, United Airlines.
How much is a flight from Chicago to San Juan?+−
The lowest fare we have observed is $227, found on 11 Aug 2026. Prices move, so read it as a floor rather than a quote.
Which airlines fly from Chicago to San Juan?+−
These are the carriers we have seen on the route: JetBlue, Frontier Airlines, G4.
When is the cheapest month to fly from Chicago to San Juan?+−
In our observations November 2026 is the cheapest month so far, at $186.
Similar routes
Last checked: 11 Aug 2026