AirHint found the following cheapest one-way flights from Chicago (MDW) to Punta Cana (PUJ) in June 2025 (see full year).

One-Way flights

14 Jun	Frontier Airlines
30 Jun	Southwest Airlines	direct
24 Jun	Frontier Airlines
15 Jun	Frontier Airlines
13 Jun	Southwest Airlines	direct
14 Jun	Southwest Airlines	direct
18 Jun	Southwest Airlines
26 Jun	Southwest Airlines	direct
15 Jun	Southwest Airlines	direct
18 Jun	Southwest Airlines	direct

Also check the deals for return flights from Chicago to Punta Cana in June.

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 one-way flights from Chicago to Punta Cana in June from $171

One-Way flights