Cheapest return flights from Chicago to Punta Cana in May from $608

Best time to book flights for Chicago (MDW) to Punta Cana (PUJ) flights at AirHint

AirHint found the following cheapest return flights from Chicago (MDW) to Punta Cana (PUJ) in May 2025 (see full year).

Return flights

15 May - 18 May Southwest Airlines
17 May - 20 May Southwest Airlines
25 May - 01 Jun WestJet

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

Skyscanner

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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