San Juan → Chicago flights

San Juan (SIG, SJU)→Chicago (CGX, DPA, MDW, ORD, PWK, RFD)
from€126

Last observed price · Last checked: 26 Aug 2026 · Price may change

Find flights

Short answer

American Airlines flies San Juan to Chicago non-stop. The lowest fare our own searches returned is €126, seen on 26 Aug 2026. September 2026 is the cheapest month in our observations, at €126. These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare.

Selected search
Last checked: 26 Aug 2026 · Price may change
€126
Wed 2 Sep 2026 → Sun 6 Sep 2026
Frontier AirlinesNon-stop4 nights
Cheapest
Last checked: 26 Aug 2026 · Price may change
€126 lowest5h 13m fastest
Options found on this date
FAFrontier Airlines19:14 · Non-stop€126
View ticket →

Tickets found in the last 7 days

The lowest fares our queries caught, cheapest first.

FA€126Cheapest2 Sep 2026 → 6 Sep 2026Frontier Airlines · Non-stop · 19:14Last checked: 26 Aug 2026 · Price may change4 nightsView ticket →SA€14424 Sep 2026 → 27 Sep 2026Southwest Airlines · 1 stop · 20:55Last checked: 26 Aug 2026 · Price may change3 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: 26 Aug 2026
San Juan → ChicagoWed 2 Sep 2026 · €126
Find flights

Route facts

Direct flights
Non-stop
SIG - CGX, 5h 13m
Airlines seen
2
American Airlines, United Airlines
Cheapest month
September 2026
€126
Typical duration
5h 13m
3305 km
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 €126, found on 26 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: American Airlines, United Airlines.

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

In our observations September 2026 is the cheapest month so far, at €126.

Similar routes

San Juan → Miami€105Mexico City → Chicago€241San Juan → Philadelphia€120Guadalajara → Chicago€286San Juan → New York€125Los Angeles → Chicago€124San Juan → Orlando€116Dallas → Chicago€129

More routes from San Juan

San Juan → Miami€105San Juan → Philadelphia€120San Juan → New York€125San Juan → Orlando€116San Juan → Boston€133San Juan → Fort Lauderdale€106San Juan → Santo Domingo€103San Juan → Medellin€159San Juan → Baltimore€171San Juan → Madrid€569San Juan → Bogota€212San Juan → Hartford€146San Juan → Washington€243San Juan → Tampa€124San Juan → Charlotte€214San Juan → Raleigh€340San Juan → Houston€173San Juan → Punta Cana€189San Juan → Cleveland€118San Juan → Jacksonville€119San Juan → Atlanta€229San Juan → AntalyaSan Juan → Denver€270San Juan → Dallas€354San Juan → Malaga€763San Juan → Buenos Aires€610

More routes to Chicago

Mexico City → Chicago€241Guadalajara → Chicago€286Los Angeles → Chicago€124Dallas → Chicago€129New York → Chicago€155Atlanta → Chicago€92Denver → Chicago€95Minneapolis → Chicago€139Cincinnati → Chicago€125Montreal → Chicago€244Istanbul → Chicago€498Amman → Chicago€500New Orleans → Chicago€191Fort Lauderdale → Chicago€127Phoenix → Chicago€140Houston → Chicago€200Baltimore → Chicago€69Miami → Chicago€140Las Vegas → Chicago€140San Diego → Chicago€203Detroit → Chicago€194Paris → Chicago€480Brussels → Chicago€686Guatemala City → Chicago€255London → Chicago€491Toronto → Chicago€161Dubai → Chicago€666Munich → Chicago€571Copenhagen → Chicago€411Dublin → Chicago€255

Last checked: 26 Aug 2026