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

Return flights

08 Sep - 17 Sep	Southwest Airlines
01 Sep - 04 Sep	Southwest Airlines
01 Sep - 05 Sep	Southwest Airlines
02 Sep - 06 Sep	Southwest Airlines
28 Sep - 04 Oct	Southwest Airlines
12 Sep - 14 Sep	Frontier Airlines
11 Sep - 14 Sep	Frontier Airlines
05 Sep - 14 Sep	Frontier Airlines
25 Sep - 09 Oct	Southwest Airlines
18 Sep - 20 Sep	Frontier Airlines
22 Sep - 25 Sep	Frontier Airlines
27 Sep - 11 Oct	Southwest Airlines
15 Sep - 18 Sep	Frontier Airlines

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

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 September from 292€

Return flights