Cheap flights from Chicago to Punta Cana from $123

If you’re not able to fly to Punta Cana in September, then August is your next best option. Flight prices from Chicago to Punta Cana during August average around $457.

The cheapest day to depart from Chicago to Punta Cana is on a Monday when prices can be found for as low as $483. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Thursday is $552.

In the evening is the cheapest time of day to fly from Chicago to Punta Cana when you can find flight prices for as low as $374. 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 $524 per ticket.

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

You are more likely to see cheaper flights to Punta Cana from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Punta Cana for around $490 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 for as low as $426 on momondo.

There are 3 cabin classes available to choose from on Chicago to Punta Cana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago to Punta Cana.

As of February 2026, prices for Chicago to Punta Cana flights are approximately 37% more expensive when compared to flights at the same time last year.

Arajet, Frontier, and Southwest are the most popular carriers operating from Chicago to Punta Cana

American Airlines, Frontier and United Airlines are the top three most popular airlines that fly to Punta Cana from Chicago according to our data. American Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Punta Cana. Keep in mind that there are 12 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 17% 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 134 minutes.

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

Thursday 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, TUI fly have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

New York (JFK) was the most common stop: 32% 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 23m.

Charlotte (CLT) has the shortest average layover time for this route: 1h 07m.

The number of flights available between Chicago and Punta Cana is 2 per day as of February 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

As of February 2026, there are 19 flights per week flying from Chicago to Punta Cana. The most common day of the week flights depart is Sat, with 32% of flights taking off on this day.