Cheapest one-way flights from Chicago to San Juan in April from $75

AirHint found the following cheapest one-way flights from Chicago (ORD) to San Juan (SJU) in April 2026 (see full year).

One-Way flights

24 Apr jetBlue
16 Apr jetBlue
19 Apr jetBlue
16 Apr Spirit Airlines direct
18 Apr Spirit Airlines direct
28 Apr Spirit Airlines direct
01 Apr United direct
21 Apr Spirit Airlines direct
11 Apr Spirit Airlines direct
20 Apr Spirit Airlines direct

Also check the deals for return flights from Chicago to San Juan in April.

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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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