$388 Find Cheap Flights from Chicago to Puerto Plata

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Puerto Plata departing on 1/25. 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

Sun, Jan 25 - Thu, Jan 29
Delta Logo
7:05 am - 3:53 pmORD-POP
6h 48m1 stop
Delta Logo
5:08 pm - 8:42 amPOP-ORD
17h 34m1 stop
$388Delta
Find Deal
Sun, Jan 25 - Thu, Jan 29
Delta Logo
7:35 pm - 3:53 pmORD-POP
18h 18m2 stops
Delta Logo
5:08 pm - 11:56 pmPOP-ORD
8h 48m1 stop
$392Delta
Find Deal
Sun, Jan 4 - Mon, Jan 12
American Airlines Logo
12:10 am - 3:33 pmORD-POP
13h 23m1 stop
American Airlines Logo
4:42 pm - 11:06 amPOP-ORD
20h 24m1 stop
$397American Airlines
Find Deal
Thu, Jan 1 - Mon, Jan 12
American Airlines Logo
5:00 am - 4:17 pmORD-POP
9h 17m2 stops
American Airlines Logo
4:42 pm - 12:11 pmPOP-ORD
21h 29m1 stop
$402American Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
9:10 pm - 1:23 pmORD-POP
14h 13m2 stops
American Airlines Logo
4:42 pm - 12:30 amPOP-ORD
9h 48m1 stop
$417American Airlines
Find Deal
Sat, Dec 6 - Fri, Dec 12
Delta Logo
6:45 am - 3:56 pmORD-POP
7h 11m1 stop
Delta Logo
5:11 pm - 12:01 amPOP-ORD
8h 50m1 stop
$423Delta
Find Deal
Sat, Dec 6 - Fri, Dec 12
American Airlines Logo
7:07 pm - 2:05 pmORD-POP
16h 58m1 stop
American Airlines Logo
2:55 pm - 11:39 pmPOP-ORD
10h 44m2 stops
$427American Airlines
Find Deal
Sat, Dec 6 - Fri, Dec 12
Delta Logo
5:30 am - 3:56 pmORD-POP
8h 26m1 stop
Delta Logo
5:11 pm - 12:01 amPOP-ORD
8h 50m1 stop
$443Delta
Find Deal
Sat, Dec 6 - Fri, Dec 12
American Airlines Logo
7:07 pm - 2:05 pmORD-POP
16h 58m1 stop
American Airlines Logo
4:38 pm - 7:19 amPOP-ORD
16h 41m2 stops
$447American Airlines
Find Deal
Thu, Jan 1 - Sun, Jan 11
Delta Logo
6:45 am - 4:00 pmORD-POP
7h 15m1 stop
Delta Logo
5:08 pm - 11:59 pmPOP-ORD
8h 51m1 stop
$456Delta
Find Deal
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 July, when the average cost of round-trip tickets is $816 and $774 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 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$388
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 14% 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 8002 reviews
8.5Crew
8.1Boarding
7.9Comfort
7.9Entertainment
7.3Food
Airline reviews

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

10.0 ExcellentWilliam, Nov 2025ATL - SJO
Read more Delta reviews

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

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