Cheapest return flights from Chicago to Punta Cana in January from $401

AirHint found the following cheapest return flights from Chicago (MDW) to Punta Cana (PUJ) in January 2026 (see full year).

Return flights

07 Jan - 13 Jan Frontier Airlines
06 Jan - 13 Jan Frontier Airlines
07 Jan - 14 Jan Frontier Airlines
30 Jan - 07 Feb Southwest Airlines
11 Jan - 18 Jan Frontier Airlines
07 Jan - 10 Jan Frontier Airlines
11 Jan - 20 Jan Frontier Airlines
22 Jan - 26 Jan Southwest Airlines
10 Jan - 16 Jan Frontier Airlines
16 Jan - 19 Jan Porter Airlines (Canada) Ltd
01 Jan - 04 Jan Frontier Airlines

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

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