Cheapest return flights from Chicago to San Juan in May from 144€

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

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

Return flights

12 May - 19 May Frontier Airlines
12 May - 15 May Frontier Airlines
16 May - 19 May Frontier Airlines
04 May - 08 May Frontier Airlines
09 May - 11 May Frontier Airlines
01 May - 05 May Frontier Airlines
01 May - 04 May Frontier Airlines
02 May - 05 May Frontier Airlines
16 May - 18 May Frontier Airlines
01 May - 06 May Delta
28 May - 04 Jun Delta
30 May - 02 Jun Southwest Airlines
30 May - 01 Jun Southwest Airlines
23 May - 01 Jun Southwest Airlines
23 May - 23 Jun Southwest Airlines

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

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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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