Cheapest one-way flights from Chicago to Punta Cana in September from 229€

Best time to book flights for Chicago (MDW) to Punta Cana (PUJ) flights at AirHint

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

One-Way flights

14 Sep Southwest Airlines
21 Sep Southwest Airlines
04 Sep Delta
10 Sep Southwest Airlines
11 Sep Southwest Airlines
17 Sep Southwest Airlines
06 Sep Delta
13 Sep Southwest Airlines
20 Sep Southwest Airlines

Also check the deals for return 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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