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

Return flights

06 Dec - 11 Dec	Delta
11 Dec - 14 Dec	Southwest Airlines
20 Dec - 25 Dec	Southwest Airlines
21 Dec - 25 Dec	Southwest Airlines
25 Dec - 31 Dec	Frontier Airlines
25 Dec - 27 Dec	Frontier Airlines
27 Dec - 30 Dec	Frontier Airlines
24 Dec - 29 Dec	Frontier Airlines
24 Dec - 28 Dec	Frontier Airlines
20 Dec - 05 Jan	Southwest Airlines
17 Dec - 05 Jan	Southwest Airlines
25 Dec - 01 Jan	Delta
30 Dec - 03 Jan	Southwest Airlines
26 Dec - 02 Jan	Southwest Airlines

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 471€

Return flights