San Juan → Chicago flights
San Juan (SIG, SJU)→Chicago (CGX, DPA, MDW, ORD, PWK, RFD)
from$151
Last observed price · Last checked: 11 Aug 2026 · Price may change
Selected search
Last checked: 11 Aug 2026 · Price may change
$151
Mon 31 Aug 2026 → Fri 11 Sep 2026
Southwest Airlines1 stop5h 45m11 nights
CheapestLast checked: 11 Aug 2026 · Price may change
$151 lowest$210 average5h 45m fastest
Tickets found in the last 7 days
The lowest fares our queries caught, cheapest first.
SA$151Cheapest31 Aug 2026 → 11 Sep 2026Southwest Airlines · 1 stop · 20:55Last checked: 11 Aug 2026 · Price may change11 nightsView ticket →JE$15525 Oct 2026 → 29 Oct 2026JetBlue · 1 stop · 06:25Last checked: 11 Aug 2026 · Price may change4 nightsView ticket →FA$1563 Sep 2026 → 7 Sep 2026Frontier Airlines · 1 stop · 06:35Last checked: 11 Aug 2026 · Price may change4 nightsView ticket →SA$17819 Aug 2026 → 24 Aug 2026Southwest Airlines · 1 stop · 05:15Last checked: 11 Aug 2026 · Price may change5 nightsView ticket →FA$29115 Oct 2026 → 18 Oct 2026Frontier Airlines · 1 stop · 21:49Last checked: 11 Aug 2026 · Price may change3 nightsView ticket →JE$32920 Oct 2026 → 24 Oct 2026JetBlue · 1 stop · 06:25Last checked: 11 Aug 2026 · Price may change4 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
San Juan → ChicagoMon 31 Aug 2026 · $151
Find flightsRoute facts
Direct flights
Non-stop
SIG - CGX, 5h 45m
Airlines seen
3
JetBlue, Frontier Airlines, Southwest Airlines
Cheapest month
August 2026
$151
Average observed
$210
Typical duration
5h 45m
Alternative airports
6
SJU, DPA, MDW, ORD, PWK, RFD
Frequently asked
Are there direct flights from San Juan to Chicago?+−
Yes. We have seen non-stop flights on this route, flown by American Airlines, United Airlines.
How much is a flight from San Juan to Chicago?+−
The lowest fare we have observed is $151, found on 11 Aug 2026. Prices move, so read it as a floor rather than a quote.
Which airlines fly from San Juan to Chicago?+−
These are the carriers we have seen on the route: JetBlue, Frontier Airlines, Southwest Airlines.
When is the cheapest month to fly from San Juan to Chicago?+−
In our observations August 2026 is the cheapest month so far, at $151.
Similar routes
Last checked: 11 Aug 2026