Cheapest one-way flights from Chicago to Punta Cana in October from $236

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

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

One-Way flights

20 Oct American Airlines direct
28 Oct American Airlines direct
27 Oct American Airlines direct
17 Oct Copa
05 Oct American Airlines
29 Oct American Airlines
22 Oct Copa
08 Oct Copa
17 Oct American Airlines direct
16 Oct American Airlines

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

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