ORD - POP

$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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$496
Typical prices: $764-$573
Copa Airlines
Mon 9/21Fri 9/25
ORD - POP • 1 stop
Cheapest one-way
$243
Typical prices: $216-$472
Air Canada
Tue 4/21
ORD - POP • 1 stop
Top airlines
Cheapest • from $496 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Puerto Plata. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $543 (round-trip)
Shortest trip • 6h 42m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 33% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Puerto Plata!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Puerto Plata (ORD-POP)

 
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

Mon, Sep 21 - Fri, Sep 25
Copa Airlines Logo
3:20 pm - 11:32 am
ORD
-
POP
19h 12m
1 stop
Copa Airlines Logo
12:41 pm - 1:02 am
POP
-
ORD
13h 21m
1 stop
$496Copa Airlines
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 - 7:44 am
POP
-
ORD
17h 20m
1 stop
$626JetBlue
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 - Thu, Jun 11
American Airlines Logo
5:00 am - 12:36 pm
ORD
-
POP
6h 36m
1 stop
American Airlines Logo
1:26 pm - 12:24 am
POP
-
ORD
11h 58m
1 stop
$632American 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
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 September.

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, where tickets cost $410 (return) on average. On the other hand, the most expensive months are July and June, where 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 9% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago to Puerto Plata

When to book flights from Chicago to Puerto Plata

Are your dates flexible? Find out the best times to travel from Chicago to Puerto Plata based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Puerto Plata flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Puerto Plata?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Puerto Plata was $243 for a one-way ticket and $496 for a round-trip.

  • Do I need a passport to fly between Chicago and Puerto Plata?

    Yes

  • Which airports will I be using when flying from Chicago to Puerto Plata?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Puerto Plata, also known as Puerto Plata La Union.

  • Which aircraft models fly most regularly from Chicago to Puerto Plata?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Puerto Plata?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Puerto Plata, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Puerto Plata, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Puerto Plata are Delta and American Airlines. With an average price for the route of $523 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $615 and an overall rating of 7.1.

  • 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 to Puerto Plata from Chicago 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 to Puerto Plata with an airline and back to Chicago with another airline. Booking your flights between Chicago and POP can sometimes prove cheaper using this method.

  • 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 to Puerto Plata from Chicago 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 8368 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

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

2.0 MediocreWilliam, Apr 2026
LGA - BOS
Read more Delta reviews

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.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

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

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