August is the cheapest month to fly this route, with average fares around $392 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $494 | $433 | ||
| June 2026 | $498 | $420 | Peak | |
| July 2026 | $424 | $295 | ||
| August 2026 | $392 | $380 | Best |
Departing on Friday offers the lowest average fares at $431. Wednesday departures are the most expensive at $511, a difference of $80.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Chicago to Punta Cana is August, with average round-trip fares around $392. The lowest fare found in August is $380.
Friday departures are the cheapest, averaging $431 round trip. The most expensive day is Wednesday at $511.
Based on current pricing trends, booking for August travel offers the best value. Avoid June if possible, as fares average $498 compared to $392 in the cheapest month. May is a solid middle-ground option at $494.
Flying in August instead of June can save you approximately $106 per round trip. The cheapest month averages $392 while the most expensive averages $498.
Airlines, flight times, price calendar, and more for Chicago to Punta Cana
View ORD → PUJ Details