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

Return flights

01 Nov - 08 Nov	Frontier Airlines
29 Nov - 06 Dec	Frontier Airlines
01 Nov - 05 Nov	Southwest Airlines
15 Nov - 19 Nov	Delta
29 Nov - 07 Dec	Frontier Airlines
07 Nov - 09 Nov	Frontier Airlines
16 Nov - 23 Nov	Southwest Airlines
15 Nov - 18 Nov	Southwest Airlines
16 Nov - 20 Nov	Frontier Airlines
06 Nov - 11 Nov	Frontier Airlines
14 Nov - 18 Nov	Southwest Airlines
13 Nov - 18 Nov	Frontier Airlines
20 Nov - 22 Dec	Delta
25 Nov - 02 Dec	Delta
24 Nov - 01 Dec	Frontier Airlines
28 Nov - 01 Dec	Frontier Airlines
24 Nov - 02 Dec	Delta

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

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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Cheapest return flights from Chicago to Punta Cana in November from $331

Return flights