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

Return flights

10 Jan - 17 Jan	Delta
10 Jan - 17 Jan	Southwest Airlines	direct
06 Jan - 13 Jan	Frontier Airlines
25 Jan - 29 Jan	Southwest Airlines
15 Jan - 19 Jan	Frontier Airlines
07 Jan - 14 Jan	Southwest Airlines
22 Jan - 26 Jan	Southwest Airlines
16 Jan - 19 Jan	Porter Airlines (Canada) Ltd

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

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 January from $367

Return flights