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Cheap Flights from Chicago to San Juan

Every verified deal from Chicago to San Juan, ranked by how far the fare falls below its route baseline. Prices are checked against live availability.

Chicago → San Juan

$246 $0.06/mi

American · Economy · Oct 23 – Oct 26 (3n)

On the board right now

Cabin mix: 1 Economy.
Best discount right now: 51% below the route baseline.
Most active airlines: American.
1 deal first seen in the last 24 hours.

Price history: Chicago to San Juan

Lowest observed fare on this corridor over the past year, from our signals database.

$241 — seen Aug 2026
$193 — seen Aug 2026
$247 — seen Aug 2026
$268 — seen Aug 2026
$246 — seen Aug 2026
$268 — seen Aug 2026
$240 — seen Aug 2026 (21 observations)
$390 — seen Aug 2026 (6 observations)
$418 — seen Aug 2026 (6 observations)
$300 — seen Aug 2026 (10 observations)
$247 — seen Aug 2026
$247 — seen Aug 2026
$240 — seen Aug 2026 (6 observations)
$240 — seen Aug 2026 (16 observations)
$247 — seen Aug 2026
$418 — seen Aug 2026 (3 observations)
$300 — seen Aug 2026 (6 observations)
$256 — seen Aug 2026 (2 observations)
$240 — seen Aug 2026 (15 observations)
$198 — seen Aug 2026 (3 observations)
$418 — seen Aug 2026 (6 observations)
$345 — seen Aug 2026 (6 observations)
$240 — seen Aug 2026 (4 observations)
$291 — seen Aug 2026 (2 observations)
$306 — seen Aug 2026 (2 observations)
$301 — seen Aug 2026 (4 observations)
$240 — seen Aug 2026 (5 observations)
$256 — seen Aug 2026 (2 observations)
$321 — seen Aug 2026
$308 — seen Aug 2026
$240 — seen Aug 2026 (20 observations)
$326 — seen Aug 2026 (3 observations)
$300 — seen Aug 2026 (2 observations)
$321 — seen Aug 2026
$240 — seen Aug 2026 (2 observations)
$228 — seen Aug 2026
$369 — seen Aug 2026 (8 observations)
$138 — seen Aug 2026
$397 — seen Aug 2026 (7 observations)
$311 — seen Aug 2026 (7 observations)
$178 — seen Aug 2026
$397 — seen Aug 2026 (4 observations)
$311 — seen Aug 2026 (4 observations)
$369 — seen Aug 2026 (4 observations)
$397 — seen Aug 2026 (3 observations)
$311 — seen Aug 2026 (3 observations)
$369 — seen Aug 2026 (3 observations)
$138 — seen Aug 2026
$207 — seen Aug 2026
$149 — seen Aug 2026
$451 — seen Aug 2026 (3 observations)
$299 — seen Aug 2026
$439 — seen Aug 2026 (3 observations)
$512 — seen Aug 2026
$138 — seen Aug 2026
$138 — seen Aug 2026
$138 — seen Aug 2026
$138 — seen Aug 2026
$148 — seen Aug 2026
$148 — seen Aug 2026
$148 — seen Aug 2026
$138 — seen Aug 2026
$150 — seen Aug 2026 (2 observations)
$150 — seen Aug 2026 (2 observations)
$192 — seen Aug 2026
$94 — seen Aug 2026
$118 — seen Aug 2026
$118 — seen Aug 2026
$243 — seen Aug 2026 (2 observations)
$444 — seen Aug 2026
$266 — seen Aug 2026
$243 — seen Aug 2026 (7 observations)
$266 — seen Aug 2026 (12 observations)
$118 — seen Aug 2026 (2 observations)
$564 — seen Aug 2026 (3 observations)
$243 — seen Aug 2026 (3 observations)
$266 — seen Aug 2026 (10 observations)
$564 — seen Aug 2026 (3 observations)
$150 — seen Aug 2026 (2 observations)
$150 — seen Aug 2026
$160 — seen Aug 2026
$266 — seen Aug 2026 (3 observations)
$160 — seen Aug 2026 (2 observations)
$466 — seen Aug 2026 (6 observations)
$560 — seen Aug 2026 (3 observations)
$564 — seen Aug 2026 (3 observations)
$178 — seen Aug 2026
$560 — seen Aug 2026 (3 observations)
$466 — seen Aug 2026 (3 observations)
$564 — seen Aug 2026 (3 observations)
$347 — seen Aug 2026
$357 — seen Aug 2026 (9 observations)
$432 — seen Aug 2026
$326 — seen Aug 2026 (2 observations)
$178 — seen Aug 2026 (2 observations)
$347 — seen Aug 2026 (3 observations)
$357 — seen Aug 2026
$432 — seen Aug 2026 (3 observations)
$308 — seen Aug 2026 (5 observations)
$226 — seen Aug 2026
$347 — seen Aug 2026
$357 — seen Aug 2026 (4 observations)
$432 — seen Aug 2026
$182 — seen Aug 2026
$357 — seen Aug 2026 (6 observations)
$182 — seen Aug 2026
$357 — seen Aug 2026 (2 observations)
$444 — seen Aug 2026 (2 observations)
$444 — seen Aug 2026 (7 observations)
$182 — seen Aug 2026
$444 — seen Sep 2026 (4 observations)
$182 — seen Sep 2026
$182 — seen Sep 2026
$444 — seen Sep 2026 (4 observations)
$178 — seen Sep 2026
$444 — seen Sep 2026
$367 — seen Sep 2026 (3 observations)
$367 — seen Sep 2026 (5 observations)
$354 — seen Sep 2026 (4 observations)
$333 — seen Sep 2026
$354 — seen Sep 2026 (3 observations)
$354 — seen Sep 2026 (6 observations)
$217 — seen Sep 2026
$217 — seen Sep 2026
$635 — seen Sep 2026 (3 observations)
$635 — seen Sep 2026 (5 observations)
$635 — seen Sep 2026 (8 observations)
$635 — seen Sep 2026 (8 observations)
$635 — seen Sep 2026 (9 observations)
$635 — seen Sep 2026 (6 observations)
$449 — seen Sep 2026 (4 observations)
$303 — seen Sep 2026 (5 observations)
$449 — seen Sep 2026 (4 observations)
$303 — seen Sep 2026 (4 observations)
$449 — seen Sep 2026
$303 — seen Sep 2026
$412 — seen Sep 2026 (4 observations)
$366 — seen Sep 2026 (4 observations)
$412 — seen Sep 2026 (4 observations)
$329 — seen Sep 2026 (4 observations)
$1286 — seen Sep 2026 (4 observations)
$281 — seen Sep 2026
$235 — seen Sep 2026
$1286 — seen Sep 2026
$246 — seen Sep 2026

Frequently asked questions

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

There are 1 verified deals from Chicago to San Juan on the board right now. The list refreshes hourly.

What is the cheapest flight from Chicago to San Juan right now?

The lowest verified fare from Chicago to San Juan right now is $246. Prices are checked against live availability before listing.

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

The lowest fare we've recorded from Chicago to San Juan is $94, based on 145 price observations over the past year.

Which airlines fly Chicago to San Juan?

Airlines with the most deals from Chicago to San Juan right now are American.