$243 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 4/21. 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, May 26 - Sat, May 30
American Airlines Logo
7:00 am - 2:48 pm
ORD
-
POP
6h 48m
1 stop
American Airlines Logo
3:29 pm - 11:59 pm
POP
-
ORD
9h 30m
1 stop
$629American Airlines
Fri, May 1 - Tue, May 5
American Airlines Logo
8:46 pm - 2:43 pm
ORD
-
POP
16h 57m
1 stop
American Airlines Logo
3:30 pm - 12:25 am
POP
-
ORD
9h 55m
1 stop
$630American Airlines
Tue, May 26 - Thu, Jun 11
American Airlines Logo
2:24 pm - 12:36 pm
ORD
-
POP
21h 12m
1 stop
American Airlines Logo
1:26 pm - 7:57 pm
POP
-
ORD
7h 31m
1 stop
$631American Airlines
Tue, May 26 - Sat, May 30
American Airlines Logo
8:59 pm - 12:36 pm
ORD
-
POP
14h 37m
2 stops
American Airlines Logo
1:26 pm - 12:24 am
POP
-
ORD
11h 58m
1 stop
$633American Airlines
Tue, May 26 - Sun, May 31
American Airlines Logo
7:00 am - 2:48 pm
ORD
-
POP
6h 48m
1 stop
American Airlines Logo
1:26 pm - 10:33 pm
POP
-
ORD
10h 07m
1 stop
$634American Airlines
Sat, May 2 - Sat, May 9
JetBlue Logo
8:31 am - 12:46 pm
ORD
-
POP
27h 15m
1 stop
JetBlue Logo
3:24 pm - 8:59 am
POP
-
ORD
18h 35m
2 stops
$635JetBlue
Tue, May 26 - Thu, Jun 11
American Airlines Logo
7:00 am - 2:48 pm
ORD
-
POP
6h 48m
1 stop
American Airlines Logo
1:26 pm - 12:24 am
POP
-
ORD
11h 58m
1 stop
$637American Airlines
Tue, May 26 - Sun, May 31
American Airlines Logo
8:52 pm - 12:36 pm
ORD
-
POP
14h 44m
2 stops
American Airlines Logo
1:26 pm - 9:29 pm
POP
-
ORD
9h 03m
1 stop
$638American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
8:46 pm - 2:37 pm
ORD
-
POP
16h 51m
2 stops
American Airlines Logo
1:26 pm - 11:59 pm
POP
-
ORD
11h 33m
2 stops
$643American Airlines
Fri, May 15 - Fri, May 22
American Airlines Logo
5:20 pm - 2:37 pm
ORD
-
POP
20h 17m
1 stop
American Airlines Logo
1:26 pm - 9:29 pm
POP
-
ORD
9h 03m
1 stop
$646American 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 May.

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 July and June, when the average cost of round-trip tickets is $779 and $777 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 3 weeks before departure, which saves you about 35% 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$243
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 7% increase in price.
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.
7.9
DeltaOverall score based on 8377 reviews
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
8.5Crew
Airline reviews

We departed and landed early which was a nice surprise. The boarding process was slow.

10.0 ExcellentBrittany, Apr 2026
DAL - ATL
Read more Delta reviews

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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

Information on your arrival and departure airports