$162 Find Cheap Flights from Chicago O'Hare Airport to Dominican Republic - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from O'Hare Intl to the Dominican Republic

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cananonstop$362
Santo Domingo
Santo Domingo1 stop$365
Puerto Plata
Puerto Plata1 stop$550
Punta Cana
Punta Cananonstop$362
Santo Domingo
Santo Domingo1 stop$365
Puerto Plata
Puerto Plata1 stop$550
Booking Insights

KAYAK's insights & trends for O'Hare Intl to the Dominican Republic flights

Get data-powered insights and trends into flights from O'Hare Intl to the Dominican Republic to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to the Dominican Republic flight route?

The cheapest ticket to the Dominican Republic from Chicago O'Hare Intl Airport found in the last 5 days was to Punta Cana, at $329 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $329.

What is the cheapest time of day to fly to the Dominican Republic?

The cheapest time of day to fly to the Dominican Republic is generally at night, when round-trip flights cost $470 on average. The most expensive time of day to fly to the Dominican Republic is generally in the morning, which is peak travel time and where the average cost of a ticket is $581.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to the Dominican Republic?

No, with an average price for the route of $630, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to the Dominican Republic?

The cheapest month for flights from Chicago O'Hare Intl Airport to the Dominican Republic is January, when tickets cost $439 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $668 and $626 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Dominican Republic?

For Chicago O'Hare Airport to Dominican Republic, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Dominican Republic back to Chicago O'Hare Airport, the best deals are generally found on Wednesday, with Monday being the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to the Dominican Republic?

To get a below average price on the flight from Chicago O'Hare Intl Airport to the Dominican Republic, 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 3 weeks before departure.

Good to know

Low season

September

Cheapest flight

$162
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Airport to Punta Cana

FAQs - booking Dominican Republic flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Dominican Republic?

    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 O'Hare Airport to Dominican Republic.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Dominican Republic?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Dominican Republic 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 O'Hare Airport to Dominican Republic?

    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 O'Hare Airport to Dominican Republic 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 O'Hare Airport to Dominican Republic?

    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 O'Hare Airport to Dominican Republic up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago O'Hare Intl Airport and Dominican Republic per day?

    Each day, there are between 1 and 2 nonstop flights that take off from Chicago O'Hare Intl Airport and land in the Dominican Republic, with an average flight time of 4h 42m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at Punta Cana. Each week, there are 6 flights. The most frequent day of departure is Monday, when 33% of all weekly flights depart. The fewest flights depart on a Tuesday.

Reviews of the top 5 airlines serving from O'Hare Intl to the Dominican Republic

 
Need help choosing which airline to fly with from O'Hare Intl to the Dominican Republic? 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.
7.4
United AirlinesOverall score based on 10146 reviews
7.1Entertainment
7.7Boarding
6.7Food
8.1Crew
7.3Comfort
Airline reviews

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

2.0 MediocreWilliam, Aug 2026
Read more United Airlines reviews

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The seats cushion on my seat (exit row) needs to be replaced. It felt like I was sitting on a bar rather than a seat cushion. Also, I was in the middle seat and I sat next to an oversized guy (window seat) and he took up about 25% of my space. Otherwise, the experience was good. :)

The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.

Good flight, regional jet so old and seats could use an upgrade

Couldn't make the flight because connecting flight was canceled.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

First time flying JetBlue and my perception changed. Love it.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

I have flown Jet Blue many times between JFK and SFO. I appreciate how clean the planes are, the ability to select my onboard entertainment and the flight crews have always been amazing! Unfortunately, my trip from SFO to JFK on August 23 was unusual. I arrived early at SFO for the 12:00 noon scheduled boarding. The flight was supposed to take off at 12:45pm but after sitting for a while, the plane had to return to the gate to have a generator inspected. After deplaning and then reboarding, we eventually took off around 3:30 pm. It was explained to the passengers that because the plane was using a backup generator, additional fuel was needed and the flight would take longer than originally scheduled. We were originally supposed to arrive at JFK at 9:32 pm but instead, arrived at midnight. Unfortunately, I was exhausted for the funeral I attended the next morning. As a passenger, I have always expected that the plane will be in good mechanical order and that all parts will function as expected. I'm not entirely certain that if I fly Jet Blue in the future, that I will have the same level of confidence that I had become accustomed to. Thanks for the opportunity to provide this feedback. Kathy Nigro

The series of delays were very unfortunately - first the captain timed out, then the new captain didn't show up when we were told he would, then the first officer timed out. Those delays were compounded by after boarding, weather came in - obviously that's out of JB's control but it was frustrating after all of the other delays that seemed avoidable.

3 hours late JetBlue flight made me miss my connecting flight to Nairobi Kenya, they did not even offer me hotel accommodation, I paid out of my pocket, they did not know where my luggage was, let say my experience with JetBlue was nightmare.

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

There was a fowl odour coming from the lavatory the entire flight

The flights are back on time and everything else runs perfectly.

Surly, unhelpful ground staff at JFK. There was a complete lack of empathy—a flawed check-in ordeal caused us to miss our flight. All airlines that I have ever flown would have worked to help me solve the ticket problem. Instead, frontline employees shrugged their shoulders and pointed fingers at us for having made an error. I will do anything to avoid EVER flying on Jet Blue again. It well deserves its low rank among airlines.

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

Everything you need to know for your flight from O'Hare Intl to the Dominican Republic

Information on your arrival and departure airports