Cheapest return flights from Chicago to Punta Cana in May from $443

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

Return flights

05 May - 16 May Southwest Airlines
09 May - 13 May Delta
18 May - 30 May Southwest Airlines
09 May - 16 May Southwest Airlines
02 May - 14 May Southwest Airlines
02 May - 09 May Delta
02 May - 16 May Delta
14 May - 18 May Southwest Airlines
02 May - 09 May Southwest Airlines direct
16 May - 23 May Southwest Airlines direct
21 May - 02 Jun Porter Airlines (Canada) Ltd
26 May - 05 Jun WestJet
22 May - 01 Jun Porter Airlines (Canada) Ltd

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

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