Cheapest return flights from Chicago to Punta Cana in September from $558

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

Return flights

14 Sep - 17 Sep Delta
07 Sep - 10 Sep Delta
28 Sep - 01 Oct Delta
26 Sep - 01 Oct Delta
10 Sep - 13 Sep Porter Airlines (Canada) Ltd
25 Sep - 29 Sep Delta
25 Sep - 28 Sep Delta
24 Sep - 29 Sep Air Transat
17 Sep - 21 Sep Porter Airlines (Canada) Ltd
24 Sep - 27 Sep Southwest Airlines
17 Sep - 20 Sep Southwest Airlines

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

Powered by

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

Feel free to contact us with any feedback or request another flight research.