$182 Find Cheap Flights from Chicago to Puerto Plata

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Puerto Plata departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Puerto Plata

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Puerto Plata, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Puerto Plata, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Puerto Plata Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Puerto Plata that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Puerto Plata

Sat, Jan 10 - Sat, Jan 17
Delta Logo
5:30 am - 3:53 pm
ORD
-
POP
8h 23m1 stop
Delta Logo
5:08 pm - 11:59 pm
POP
-
ORD
8h 51m1 stop
$388Delta
Thu, Jan 8 - Sat, Feb 14
Delta Logo
5:30 am - 3:53 pm
ORD
-
POP
8h 23m1 stop
Delta Logo
4:55 pm - 8:44 pm
POP
-
ORD
29h 49m2 stops
$392Delta
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
7:30 pm - 3:42 pm
ORD
-
POP
18h 12m1 stop
American Airlines Logo
4:42 pm - 12:30 am
POP
-
ORD
9h 48m1 stop
$397American Airlines
Wed, Jan 21 - Wed, Jan 28
American Airlines Logo
4:49 pm - 3:42 pm
ORD
-
POP
20h 53m1 stop
American Airlines Logo
4:42 pm - 9:05 am
POP
-
ORD
18h 23m2 stops
$402American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
7:56 pm - 2:32 pm
ORD
-
POP
16h 36m1 stop
American Airlines Logo
4:42 pm - 9:05 am
POP
-
ORD
18h 23m1 stop
$413American Airlines
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
9:10 pm - 2:32 pm
ORD
-
POP
15h 22m2 stops
American Airlines Logo
4:42 pm - 7:22 am
POP
-
ORD
16h 40m2 stops
$417American Airlines
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
3:21 pm - 2:32 pm
ORD
-
POP
21h 11m1 stop
American Airlines Logo
4:42 pm - 7:22 am
POP
-
ORD
16h 40m2 stops
$418American Airlines
Sat, Jan 17 - Sun, Jan 25
American Airlines Logo
7:48 pm - 2:32 pm
ORD
-
POP
16h 44m2 stops
American Airlines Logo
4:42 pm - 9:05 am
POP
-
ORD
18h 23m1 stop
$432American Airlines
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
4:41 pm - 2:07 pm
ORD
-
POP
19h 26m1 stop
American Airlines Logo
4:42 pm - 12:30 am
POP
-
ORD
9h 48m1 stop
$434American Airlines
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
4:41 pm - 2:07 pm
ORD
-
POP
19h 26m1 stop
American Airlines Logo
4:42 pm - 7:22 am
POP
-
ORD
16h 40m2 stops
$438American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Puerto Plata flights

Get data-powered insights and trends into flights from Chicago to Puerto Plata to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Puerto Plata?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Puerto Plata, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Puerto Plata is October, when tickets cost $410 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $816 and $780 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Puerto Plata?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Puerto Plata, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Puerto Plata, you should book around 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$182
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Chicago to Puerto Plata

FAQs - booking Puerto Plata flights

  • How does KAYAK find such low prices on flights from Chicago to Puerto Plata?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Puerto Plata.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Puerto Plata?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Puerto Plata is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Puerto Plata?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Puerto Plata with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Puerto Plata?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Puerto Plata up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Puerto Plata?

    The cheapest time of day to fly to Puerto Plata is generally in the morning, when round-trip flights cost $681 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Puerto Plata is generally at night, which is peak travel time and where the average cost of a ticket is $787.

Reviews of the top airlines flying from Chicago to Puerto Plata

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Puerto Plata. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Puerto Plata? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8008 reviews
7.9Entertainment
8.5Crew
7.9Comfort
7.3Food
8.1Boarding
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Everything you need to know for your flight from Chicago to Puerto Plata

Information on your arrival and departure airports