AirHint found the following cheapest return flights from Chicago (MDW) to Punta Cana (PUJ) in May 2026 (see full year).
Return flights
| 22 May - 30 May | Air Transat | ||
| 14 May - 18 May | Southwest Airlines | ||
| 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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