Chicago to San Juan flights

Find your dates. Discover your next journey.

Airlines seen: Aerolineas Argentinas, Air Canada, Arajet, Avianca, Copa Airlines, Frontier Airlines +5 more
Typical journey time: 35h

Fare seen

€754Seen on 22 Sep 2026

Last checked

11 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €372

Lowest observed

9 Nov 2026

Aerolineas Argentinas · 3 stops · One way

Cheapest observed day · Last checked: 22 Sep 2026

Departure

04:20

When to fly

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Find the dates that work for you

The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

Prices are for observed departure and return date pairs. No data does not mean no flights.

Short answer

We have seen Aerolineas Argentinas fares from Chicago to San Juan. These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare. Fare seen: €754 on 22 Sep 2026.

About this route

Explore the fares we observed from Chicago to San Juan. Prices move often, so pick your dates to see the latest options.

Route distance: 8,394 km
Typical journey time: 35h
Airlines seen: Aerolineas Argentinas, Air Canada, Arajet, Avianca, Copa Airlines, Frontier Airlines +5 more
Seen on fares with a connection: LATAM Airlines, Arajet, Copa Airlines, Aerolineas Argentinas, Air Canada, JetSmart +2 more
Alternative airports: CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
We have not observed non-stop service on this route; the fares shown include at least one stop.

A clearer picture of your fare

Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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The price is final on the provider's site, where your booking is completed.

How our prices work

Airport to city: straight-line distance

Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.

Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.

Frequently asked

How much was a flight from Chicago to San Juan?

A fare of €754 was seen on 22 Sep 2026. Fares change, so search your dates for the current price.

Are there direct flights from Chicago to San Juan?

Our data holds no non-stop flight from Chicago to San Juan. The fares on this page include at least one stop.

Which airlines fly from Chicago to San Juan?

These are the carriers we have seen on the route: Aerolineas Argentinas, Air Canada, Arajet, Avianca, Copa Airlines, Frontier Airlines +5 more.

How long does the flight from Chicago to San Juan take?

The average journey time across the 79 fares we observed is 40h 09m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.

How many of the observed Chicago to San Juan fares were non-stop?

None of the 80 fares we observed was non-stop; every one included at least one stop. That describes our observations, not every flight that operates.

How observed prices work, what "No data" means and what a fare includes: Read the flight price guide