Cheap Flights from San Juan to Chicago

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The latest fare from San Juan to Chicago: $205 round trip, Jan 11 – Jan 18, seen Nov 5. Prices by month are below.

Across 4 months of observations from San Juan to Chicago, the lowest round-trip economy fare we recorded was $148, in August. The typical economy fare was $207. August was the cheapest month we saw and November the dearest.

The most recent economy price we saw on this route was $205 on Frontier, seen Nov 5.

See every deal from San Juan, to Chicago, or the return direction Chicago to San Juan.

Latest economy price we saw: San Juan to Chicago

The most recent economy round-trip fare we saw on this route.

From	Price	Per mile	Travel dates	Airline	Seen	Check price
San Juan (SJU) to Chicago (ORD)	$205	4.9¢	Jan 11 – Jan 18	Frontier	Nov 5	Check price

Economy price history: San Juan to Chicago

The lowest fares we saw each month.

Month	Low	Typical	Sightings
Nov 2026	$186	$210	7
Oct 2026	$152	$190	22
Sep 2026	$152	$206	19
Aug 2026	$148	$222	30

Frequently asked questions

How many flight deals from San Juan to Chicago are on Sparkflights right now?

There are 0 deals from San Juan to Chicago on the board right now.

What is the lowest price ever seen from San Juan to Chicago?

The lowest economy fare we've recorded from San Juan to Chicago is $148, based on 78 price observations over 4 months.

How much does a flight from San Juan to Chicago cost?

The typical round-trip economy fare we observed from San Juan to Chicago is $207, against a recorded low of $148. These are observations, not quotes.

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

For economy fares from San Juan to Chicago, August was the cheapest month we observed and November the dearest, over 4 months of data.

What is the current price from San Juan to Chicago?

The most recent economy fare we saw from San Juan to Chicago is $205, on Nov 5.