Cheapest return flights from Chicago to San Juan in June from 321€

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

06 Jun - 11 Jun United
10 Jun - 17 Jun United
07 Jun - 12 Jun United
03 Jun - 11 Jun United
27 Jun - 02 Jul United
05 Jun - 10 Jun United
14 Jun - 21 Jun United
20 Jun - 24 Jun United
14 Jun - 24 Jun United
06 Jun - 09 Jun Southwest Airlines
25 Jun - 01 Jul United
05 Jun - 14 Jun United
20 Jun - 19 Jul United direct
26 Jun - 01 Jul Southwest Airlines
29 Jun - 04 Jul United
27 Jun - 02 Jul United direct
25 Jun - 01 Jul United direct
13 Jun - 04 Jul United
26 Jun - 01 Jul United direct
29 Jun - 04 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