Cheapest return flights from Chicago to San Juan in May from 191€

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

Return flights

06 May - 12 May Frontier Airlines
08 May - 11 May Frontier Airlines
15 May - 20 May Frontier Airlines
15 May - 19 May Frontier Airlines
08 May - 10 May Frontier Airlines
13 May - 17 May Frontier Airlines
03 May - 10 May Southwest Airlines
13 May - 18 May Southwest Airlines
14 May - 19 May Southwest Airlines
25 May - 29 May 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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