Cheapest return flights from Chicago to Punta Cana in May from $334

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

10 May - 14 May Delta
05 May - 14 May Delta
07 May - 14 May Delta
06 May - 15 May Delta
17 May - 24 May Delta
04 May - 12 May Frontier Airlines
11 May - 15 May Frontier Airlines
16 May - 24 May Frontier Airlines
02 May - 04 May Frontier Airlines
03 May - 09 May Frontier Airlines
26 May - 03 Jun Frontier Airlines
30 May - 03 Jun Frontier Airlines
28 May - 01 Jun Frontier Airlines
28 May - 02 Jun Frontier Airlines
28 May - 07 Jun Frontier Airlines

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

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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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