Cheapest return flights from Chicago to Punta Cana in May from $240

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

Return flights

15 May - 21 May Arajet direct
16 May - 21 May Arajet direct
11 May - 16 May Arajet direct
09 May - 16 May Arajet direct
15 May - 17 May Arajet direct
08 May - 17 May Arajet direct
01 May - 03 May Arajet direct
18 May - 23 May Arajet direct
16 May - 23 May Arajet direct
11 May - 17 May Arajet direct
30 May - 04 Jun Frontier Airlines
26 May - 02 Jun Frontier Airlines
30 May - 05 Jun Frontier Airlines
30 May - 04 Jun Arajet direct
29 May - 05 Jun Frontier Airlines
26 May - 05 Jun United
29 May - 02 Jun United
31 May - 11 Jun Spirit Airlines
31 May - 15 Jun Spirit Airlines
31 May - 12 Jun Spirit Airlines

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

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.