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

Return flights

02 Dec - 10 Dec	Delta
05 Dec - 10 Dec	Frontier Airlines
24 Dec - 30 Dec	Frontier Airlines
05 Dec - 09 Dec	Frontier Airlines
24 Dec - 31 Dec	Frontier Airlines
06 Dec - 12 Dec	Southwest Airlines
05 Dec - 11 Dec	Southwest Airlines
03 Dec - 10 Dec	Delta
12 Dec - 14 Dec	Frontier Airlines
11 Dec - 14 Dec	Frontier Airlines
27 Dec - 03 Jan	Porter Airlines (Canada) Ltd
30 Dec - 03 Jan	Frontier Airlines
26 Dec - 02 Jan	Frontier Airlines
29 Dec - 03 Jan	Porter Airlines (Canada) Ltd
26 Dec - 03 Jan	Frontier Airlines
28 Dec - 05 Jan	WestJet

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

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 December from $367

Return flights