$302 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 5/18. 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

Thu, May 7 - Tue, May 12
American Airlines Logo
8:46 pm - 2:37 pm
ORD
-
POP
16h 51m
2 stops
American Airlines Logo
3:37 pm - 7:24 am
POP
-
ORD
16h 47m
2 stops
$603American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
5:20 pm - 2:37 pm
ORD
-
POP
20h 17m
1 stop
American Airlines Logo
3:37 pm - 10:57 pm
POP
-
ORD
8h 20m
1 stop
$613American Airlines
Sat, May 2 - Sat, May 9
JetBlue Logo
6:00 am - 12:46 pm
ORD
-
POP
29h 46m
2 stops
JetBlue Logo
3:24 pm - 8:59 am
POP
-
ORD
18h 35m
2 stops
$616JetBlue
Sat, May 2 - Sat, May 9
JetBlue Logo
6:00 am - 12:46 pm
ORD
-
POP
29h 46m
2 stops
JetBlue Logo
3:24 pm - 7:44 am
POP
-
ORD
17h 20m
1 stop
$626JetBlue
Tue, May 26 - Thu, Jun 11
American Airlines Logo
4:05 pm - 12:36 pm
ORD
-
POP
19h 31m
1 stop
American Airlines Logo
1:26 pm - 9:29 pm
POP
-
ORD
9h 03m
1 stop
$632American Airlines
Mon, May 11 - Mon, May 18
American Airlines Logo
8:46 pm - 2:37 pm
ORD
-
POP
16h 51m
2 stops
American Airlines Logo
3:37 pm - 12:25 am
POP
-
ORD
9h 48m
1 stop
$633American Airlines
Mon, May 25 - Sun, May 31
American Airlines Logo
6:00 pm - 12:36 pm
ORD
-
POP
17h 36m
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
Mon, May 25 - Sun, May 31
American Airlines Logo
8:57 pm - 12:36 pm
ORD
-
POP
14h 39m
2 stops
American Airlines Logo
1:26 pm - 10:33 pm
POP
-
ORD
10h 07m
1 stop
$638American Airlines
Mon, May 11 - Mon, May 18
American Airlines Logo
5:20 pm - 2:37 pm
ORD
-
POP
20h 17m
1 stop
American Airlines Logo
3:37 pm - 12:25 am
POP
-
ORD
9h 48m
1 stop
$643American 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$302
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 8% 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 8359 reviews
7.8Entertainment
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
Airline reviews

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

8.0 ExcellentLorna, Mar 2026
LAX - LIH
Read more Delta reviews

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

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.

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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

Information on your arrival and departure airports