$182 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 4/5. 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

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

Mon, Dec 1 - Wed, Dec 10
Delta Logo
6:45 am - 3:56 pmORD-POP
7h 11m1 stop
Delta Logo
5:11 pm - 10:46 pmPOP-ORD
7h 35m1 stop
$358Delta
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Mon, Nov 3 - Sat, Nov 8
American Airlines Logo
5:00 am - 3:41 pmORD-POP
8h 41m2 stops
American Airlines Logo
4:31 pm - 7:10 amPOP-ORD
16h 39m2 stops
$362American Airlines
Find Deal
Sun, Feb 15 - Wed, Feb 18
American Airlines Logo
1:54 pm - 3:20 pmORD-POP
23h 26m1 stop
American Airlines Logo
4:35 pm - 11:54 pmPOP-ORD
9h 19m1 stop
$365American Airlines
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Fri, Nov 28 - Fri, Dec 5
American Airlines Logo
6:35 pm - 4:00 pmORD-POP
19h 25m1 stop
American Airlines Logo
4:38 pm - 7:19 amPOP-ORD
16h 41m2 stops
$369American Airlines
Find Deal
Sun, Nov 30 - Sun, Dec 7
American Airlines Logo
7:17 pm - 1:48 pmORD-POP
16h 31m1 stop
American Airlines Logo
2:26 pm - 9:10 amPOP-ORD
20h 44m1 stop
$370American Airlines
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Sat, Nov 15 - Thu, Nov 20
Delta Logo
6:45 am - 3:56 pmORD-POP
7h 11m1 stop
Delta Logo
5:11 pm - 12:02 amPOP-ORD
8h 51m1 stop
$373Delta
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Thu, Mar 26 - Wed, Apr 1
Air Canada Logo
3:35 pm - 12:40 pmORD-POP
20h 05m2 stops
Air Canada Logo
2:30 pm - 10:57 amPOP-ORD
21h 27m1 stop
$504Air Canada
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Thu, Mar 26 - Wed, Apr 1
Air Canada Logo
3:35 pm - 12:40 pmORD-POP
20h 05m2 stops
Air Canada Logo
2:30 pm - 8:00 amPOP-ORD
18h 30m2 stops
$509Air Canada
Find Deal
Sun, Mar 29 - Sat, Apr 4
JetBlue Logo
1:45 pm - 12:55 pmORD-POP
22h 10m1 stop
JetBlue Logo
12:42 pm - 10:44 amPOP-ORD
23h 02m1 stop
$519JetBlue
Find Deal
Sun, Mar 29 - Sat, Apr 4
JetBlue Logo
1:45 pm - 12:55 pmORD-POP
22h 10m1 stop
JetBlue Logo
2:00 pm - 10:44 amPOP-ORD
21h 44m2 stops
$624JetBlue
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 23% 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$182
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 18% 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 7984 reviews
7.9Comfort
8.5Crew
7.9Entertainment
8.2Boarding
7.3Food
Airline reviews

Old plane and old configuration/seats but still comfortable for a morning flight

10.0 ExcellentBraulio, Oct 2025ATL - SDQ
Read more Delta reviews

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

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

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