Cheapest return flights from Chicago to San Juan in June from $209

Best time to book flights for Chicago (ORD) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in June 2025 (see full year).

Return flights

02 Jun - 06 Jun Spirit Airlines
02 Jun - 07 Jun Spirit Airlines
01 Jun - 06 Jun Spirit Airlines
03 Jun - 07 Jun Spirit Airlines
02 Jun - 08 Jun Spirit Airlines
16 Jun - 19 Jun Spirit Airlines direct
03 Jun - 14 Jun Spirit Airlines direct
08 Jun - 13 Jun Spirit Airlines direct
05 Jun - 10 Jun Spirit Airlines direct
10 Jun - 17 Jun Spirit Airlines direct
29 Jun - 02 Jul Spirit Airlines
20 Jun - 07 Jul Spirit Airlines
21 Jun - 07 Jul Spirit Airlines
27 Jun - 02 Jul Spirit Airlines
16 Jun - 01 Jul Spirit Airlines direct
28 Jun - 12 Jul Spirit Airlines
27 Jun - 02 Jul Spirit Airlines direct
30 Jun - 06 Jul Southwest Airlines
27 Jun - 06 Jul United direct
28 Jun - 03 Jul United direct

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

Skyscanner

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