Cheapest return flights from Chicago to San Juan in June from $255

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in June 2026 (see full year).

Return flights

01 Jun - 05 Jun United direct
01 Jun - 10 Jun United direct
01 Jun - 11 Jun United direct
08 Jun - 23 Jun Spirit Airlines direct
03 Jun - 10 Jun Spirit Airlines
02 Jun - 23 Jun Spirit Airlines
02 Jun - 03 Jun Spirit Airlines
02 Jun - 09 Jun Spirit Airlines
01 Jun - 03 Jun Spirit Airlines
20 Jun - 23 Jun Spirit Airlines direct
30 Jun - 16 Jul Spirit Airlines
30 Jun - 15 Jul Spirit Airlines
30 Jun - 14 Jul Spirit Airlines
30 Jun - 21 Jul Spirit Airlines
24 Jun - 14 Jul Spirit Airlines
24 Jun - 08 Jul Spirit Airlines
29 Jun - 08 Jul United direct
29 Jun - 16 Jul Spirit Airlines
29 Jun - 15 Jul Spirit Airlines
29 Jun - 14 Jul Spirit Airlines

Also check the deals for one-way flights from Chicago to San Juan in June.

Powered by

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.