Cheapest return flights from Chicago to Punta Cana in May from 445€

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

Return flights

04 May - 09 May Southwest Airlines
09 May - 16 May Southwest Airlines direct
31 May - 05 Jun Southwest Airlines
16 May - 23 May Southwest Airlines direct
29 May - 01 Jun Southwest Airlines
21 May - 25 May Porter Airlines (Canada) Ltd
26 May - 05 Jun Porter Airlines (Canada) Ltd

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

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