Cheapest return flights from Chicago to Punta Cana in October from $408

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

Return flights

30 Oct - 06 Nov Southwest Airlines
31 Oct - 04 Nov Southwest Airlines
27 Oct - 30 Oct Delta
22 Oct - 02 Nov Southwest Airlines
24 Oct - 31 Oct Frontier Airlines
25 Oct - 01 Nov Delta
22 Oct - 22 Oct Delta
24 Oct - 04 Nov Southwest Airlines
24 Oct - 28 Oct Southwest Airlines
21 Oct - 21 Oct Delta
25 Oct - 26 Oct Frontier Airlines

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

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