$265 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 10/27. 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

Tue, Oct 27 - Fri, Nov 13
Copa Airlines Logo
8:35 am - 11:30 am
ORD
-
POP
25h 55m
1 stop
Copa Airlines Logo
12:37 pm - 12:11 am
POP
-
ORD
13h 34m
1 stop
$575Copa Airlines
Mon, Dec 7 - Fri, Dec 11
Copa Airlines Logo
2:13 pm - 11:32 am
ORD
-
POP
19h 19m
1 stop
Copa Airlines Logo
12:37 pm - 12:46 pm
POP
-
ORD
26h 09m
1 stop
$602Copa Airlines
Fri, Oct 23 - Tue, Oct 27
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
1:45 pm - 11:42 pm
POP
-
ORD
10h 57m
1 stop
$618American Airlines
Fri, Oct 23 - Tue, Oct 27
American Airlines Logo
8:34 pm - 12:15 pm
ORD
-
POP
14h 41m
2 stops
American Airlines Logo
1:45 pm - 11:21 pm
POP
-
ORD
10h 36m
2 stops
$623American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
1:45 pm - 10:31 pm
POP
-
ORD
9h 46m
1 stop
$628American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
1:45 pm - 11:34 pm
POP
-
ORD
10h 49m
2 stops
$633American Airlines
Sun, Nov 15 - Sun, Nov 22
American Airlines Logo
8:57 pm - 2:00 pm
ORD
-
POP
15h 03m
2 stops
American Airlines Logo
2:55 pm - 7:16 am
POP
-
ORD
18h 21m
2 stops
$638American Airlines
Wed, Oct 7 - Mon, Oct 12
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
1:45 pm - 11:03 am
POP
-
ORD
22h 18m
1 stop
$648American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
5:00 am - 12:46 pm
ORD
-
POP
6h 46m
1 stop
American Airlines Logo
1:36 pm - 7:34 am
POP
-
ORD
18h 58m
1 stop
$650American Airlines
Sun, Nov 15 - Sun, Nov 22
American Airlines Logo
8:57 pm - 2:00 pm
ORD
-
POP
15h 03m
2 stops
American Airlines Logo
2:55 pm - 9:25 am
POP
-
ORD
20h 30m
1 stop
$653American 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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Puerto Plata?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Puerto Plata departing in October.

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 February, when tickets cost $182 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $664 and $658 respectively.

Good to know

Low seasonAugust
Cheapest flight$265
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 21% 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.

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.
7.8
DeltaOverall score based on 8423 reviews
8.1Boarding
7.8Entertainment
7.2Food
8.5Crew
7.8Comfort
Airline reviews

Very good flight. Crew was great. No issues and we even arrived early.

10.0 ExcellentAnonymous, Jun 2026
SAN - DTW
Read more Delta reviews

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

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

Information on your arrival and departure airports