Cheapest return flights from Chicago to Punta Cana in October from $342

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

Return flights

20 Oct - 23 Oct Delta
28 Oct - 04 Nov Delta
12 Oct - 18 Oct Frontier Airlines
19 Oct - 23 Oct Frontier Airlines
04 Oct - 11 Oct Frontier Airlines
16 Oct - 19 Oct Frontier Airlines
26 Oct - 02 Nov Southwest Airlines
02 Oct - 11 Oct Southwest Airlines
03 Oct - 10 Oct Frontier Airlines
16 Oct - 20 Oct Air Transat
22 Oct - 26 Oct Frontier Airlines
15 Oct - 19 Oct Frontier Airlines

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

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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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