Cheapest return flights from Chicago to Punta Cana in May from $449

AirHint found the following cheapest return flights from Chicago (MDW) to Punta Cana (PUJ) in May 2026 (see full year).

Return flights

09 May - 16 May Frontier Airlines
14 May - 18 May Frontier Airlines
01 May - 05 May Southwest Airlines
09 May - 16 May Southwest Airlines direct
26 May - 05 Jun Frontier Airlines
18 May - 25 May Southwest Airlines
15 May - 21 May Southwest Airlines
22 May - 28 May Southwest Airlines
31 May - 05 Jun Frontier Airlines
15 May - 17 May Southwest Airlines
30 May - 05 Jun Frontier Airlines
01 May - 03 May Southwest Airlines
28 May - 31 May Southwest Airlines
30 May - 04 Jun Southwest Airlines

Also check the deals for one-way flights from Chicago to Punta Cana in May.

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