Cheap flights from Chicago O'Hare Intl Airport to Punta Cana from $163

If you’re not able to fly to Punta Cana in January, then September is your next best option. Flight prices from Chicago O'Hare Intl Airport to Punta Cana during September average around $424.

The cheapest day to depart from Chicago O'Hare Intl Airport to Punta Cana is on a Monday when prices can be found for as low as $524. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Sunday is $633.

In the evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Punta Cana when you can find flight prices for as low as $440. Flying to Punta Cana in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $574 per ticket.

Fly from Chicago O'Hare Intl to Punta Cana for the best Chicago O'Hare Intl - Punta Cana flight prices

You are more likely to see cheaper flights to Punta Cana from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Punta Cana for around $531 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Punta Cana from Chicago O'Hare Intl Airport for as low as $481 on momondo.

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport to Punta Cana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Delta is the most popular carrier operating from Chicago O'Hare Intl to Punta Cana

American Airlines, Frontier and United Airlines are the top three most popular airlines that fly to Punta Cana from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Punta Cana. Keep in mind that there are 10 different airlines that fly to Punta Cana on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% of flights between Chicago and Punta Cana have experienced a delay on any given week. The average delay length over the past 12 months has been 145 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

New York (JFK) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (JFK) offer the lowest average round-trip price of $413.

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 6h 37m.

Philadelphia (PHL) has the shortest average layover time for this route: 1h 23m.

As of July 2026, there are 2 flights per day flying from Chicago O'Hare Intl Airport to Punta Cana. The most common time of day flights depart is 8:00AM, with 93% of flights taking off at noon.

As of July 2026, there are 17 flights per week flying from Chicago O'Hare Intl Airport to Punta Cana. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.