Cheapest one-way flights from Chicago to Punta Cana in May from $130

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 May 2025 (see full year).

One-Way flights

16 May Frontier Airlines
04 May Delta
15 May Frontier Airlines
11 May Delta
03 May Delta
12 May Delta
18 May Southwest Airlines
10 May Southwest Airlines
10 May Southwest Airlines direct
19 May Southwest Airlines

Also check the deals for return flights from Chicago to Punta Cana in May.

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.

Book a cheap hotel in Punta Cana

Cheap car rent in Punta Cana