Cheapest return flights from Chicago to Punta Cana in September from $341

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

Return flights

09 Sep - 18 Sep Southwest Airlines
23 Sep - 27 Sep Southwest Airlines
25 Sep - 30 Sep Southwest Airlines
11 Sep - 17 Sep Southwest Airlines
24 Sep - 02 Oct Southwest Airlines
28 Sep - 18 Oct Delta
27 Sep - 05 Oct Frontier Airlines
04 Sep - 07 Sep Southwest Airlines
26 Sep - 28 Sep Porter Airlines (Canada) Ltd
17 Sep - 21 Sep Southwest Airlines
30 Sep - 20 Oct Porter Airlines (Canada) Ltd

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

Skyscanner

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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