Cheapest return flights from Chicago (MDW) to Punta Cana (PUJ), May

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
29 May 04 Jun Allegiant Air
28 May 02 Jun Frontier Airlines
29 May 02 Jun Allegiant Air
29 May 05 Jun Allegiant Air
31 May 05 Jun Allegiant Air
29 May 31 May Frontier Airlines
31 May 04 Jun Allegiant Air
23 May 27 May Frontier Airlines
23 May 30 May Frontier Airlines
27 May 31 May Frontier Airlines
30 May 03 Jun Frontier Airlines
28 May 01 Jun Allegiant Air
24 May 28 May Delta
25 May 29 May Southwest Airlines
25 May 28 May Southwest Airlines
22 May 27 May Southwest Airlines
22 May 28 May Southwest Airlines
26 May 05 Jun Porter Airlines (Canada) Ltd
24 May 30 May Allegiant Air
27 May 01 Jun Frontier Airlines
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Updated May 21, 2026.

About these fares

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