Chicago → San Juan flights

Chicago (CGX, DPA, MDW, ORD, PWK, RFD)→San Juan (SIG, SJU)

from€191

Last observed price · Last checked: 24 Aug 2026 · Price may change

Direct flights only

Short answer

American Airlines flies Chicago to San Juan non-stop. The lowest fare our own searches returned is €191, seen on 24 Aug 2026. The average across the fares we caught is €325. October 2026 is the cheapest month in our observations, at €191. These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare.

Selected search

Last checked: 24 Aug 2026 · Price may change

€191

Wed 7 Oct 2026 → Wed 14 Oct 2026

Frontier Airlines1 stop7 nights

Cheapest

Last checked: 24 Aug 2026 · Price may change

€191 lowest€325 average5h 53m fastest

Options found on this date

FAFrontier Airlines07:11 · 1 stop€191

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Tickets found in the last 7 days

The lowest fares our queries caught, cheapest first.

FA€191Cheapest7 Oct 2026 → 14 Oct 2026Frontier Airlines · 1 stop · 07:11Last checked: 24 Aug 2026 · Price may change7 nightsView ticket →SA€20821 Nov 2026 → 26 Nov 2026Southwest Airlines · 3 stops · 16:20Last checked: 24 Aug 2026 · Price may change5 nightsView ticket →FA€23628 Aug 2026 → 31 Aug 2026Frontier Airlines · 1 stop · 00:44Last checked: 24 Aug 2026 · Price may change3 nightsView ticket →FA€3134 Nov 2026 → 8 Nov 2026Frontier Airlines · 2 stops · 14:11Last checked: 24 Aug 2026 · Price may change4 nightsView ticket →AA€3837 Jan 2027 → 11 Jan 2027American Airlines · Non-stop · 15:00Last checked: 24 Aug 2026 · Price may change4 nightsView ticket →AA€45114 Jan 2027 → 17 Jan 2027American Airlines · 1 stop · 08:00Last checked: 24 Aug 2026 · Price may change3 nightsView ticket →FA€49531 Dec 2026 → 4 Jan 2027Frontier Airlines · Non-stop · 23:50Last checked: 24 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: 24 Aug 2026

Chicago → San JuanWed 7 Oct 2026 · €191

Find flights

Route facts

Direct flights

Non-stop

CGX - SIG, 5h 53m

Airlines seen

American Airlines

Cheapest month

October 2026

€191

Average observed

€325

Typical duration

5h 53m

3305 km

Alternative airports

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.

How much is a flight from Chicago to San Juan?+

The lowest fare we have observed is €191, found on 24 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: American Airlines.

When is the cheapest month to fly from Chicago to San Juan?+

In our observations October 2026 is the cheapest month so far, at €191.

More routes to San Juan

Last checked: 24 Aug 2026