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

Return flights

22 Sep - 27 Sep	Southwest Airlines
30 Sep - 04 Oct	Southwest Airlines
13 Sep - 20 Sep	Frontier Airlines
09 Sep - 12 Sep	Southwest Airlines
17 Sep - 23 Sep	Frontier Airlines
12 Sep - 15 Sep	Frontier Airlines
09 Sep - 13 Sep	Delta
26 Sep - 29 Sep	Frontier Airlines
19 Sep - 22 Sep	Frontier Airlines
25 Sep - 30 Sep	Southwest Airlines
29 Sep - 06 Oct	Frontier Airlines
11 Sep - 18 Sep	Delta

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.

Book a cheap hotel in Punta Cana

Cheap car rent in Punta Cana

Cheapest return flights from Chicago to Punta Cana in September from 328€

Return flights