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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 Cana1 stop$355
Santo Domingo
Santo Domingo1 stop$375
Puerto Plata
Puerto Plata1 stop$643
Punta Cana
Punta Cana1 stop$355
Santo Domingo
Santo Domingo1 stop$375
Puerto Plata
Puerto Plata1 stop$643
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to the Dominican Republic flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago O'Hare Intl Airport to the Dominican Republic cheaper or more expensive than last year?

Fares from Chicago O'Hare Intl Airport to the Dominican Republic are running about the same as they were around this time last year, averaging $546 round-trip.

What are the cheapest fares from Chicago O'Hare Intl Airport to the Dominican Republic right now?

Here are the cheapest round-trip fares from Chicago O'Hare Intl Airport to the Dominican Republic on KAYAK in the last week:

• Punta Cana (PUJ) from $355
• Santo Domingo Las Americas (SDQ) from $375
• La Romana (LRM) from $450
• Puerto Plata La Union (POP) from $643
• Santiago de los Caballeros (STI) from $874

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

February is the cheapest time of year to fly, with average fares of $437. Prices are highest in June, when average flight costs increase to around $660.

When is the best time to book flights from Chicago O'Hare Intl Airport to the Dominican Republic?

Book your flights 3 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 16% compared to booking last-minute (within 2 weeks of departure).

Which airport in the Dominican Republic is the cheapest to fly to from Chicago O'Hare Intl Airport?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the Dominican Republic are:

• Santo Domingo Las Americas (SDQ) from $529
• Punta Cana (PUJ) from $554
• Santiago de los Caballeros (STI) from $598

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

Monday tends to be the cheapest day to fly from Chicago O'Hare Intl Airport to the Dominican Republic, while Thursday is the most expensive. Fares run about 20% higher that day, based on the past 12 months of KAYAK data.

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

Data from the past 12 months shows it's cheapest to fly to the Dominican Republic during the afternoon with average prices of $455. The morning is the most expensive time to fly, with average prices of $579.

Key details for Chicago O'Hare Intl Airport to the Dominican Republic flights

Low season

September

Cheapest flight

$143
Beat the crowds with an average 57% drop in travelers.
The most popular month to fly with an average 109% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Punta Cana

Your Chicago O'Hare Intl Airport to the Dominican Republic flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago O'Hare Intl Airport to the Dominican Republic?

    Yes. Fares from Chicago O'Hare Intl Airport to the Dominican Republic are low right now. As a rule of thumb, a round-trip under $411 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago O'Hare Intl Airport to the Dominican Republic?

    Over the past 12 months, round-trip fares from Chicago O'Hare Intl Airport to the Dominican Republic have ranged from $411 to $734.

  • What are the main airports serving the Dominican Republic?

    The Dominican Republic has 5 airports. The three busiest are Punta Cana (PUJ) (83% of arrivals), Santo Domingo Las Americas (SDQ) (12%) and Santiago de los Caballeros (STI) (3%).

  • What airlines fly nonstop from Chicago O'Hare Intl Airport to the Dominican Republic?

    Based on the flight schedule for the next 3 months, 3 airlines offer nonstop flights on this route:

    • American Airlines
    • United Airlines
    • Arajet

  • Where in the Dominican Republic can I fly nonstop from Chicago O'Hare Intl Airport?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Chicago O'Hare Intl Airport to Punta Cana.

  • Is it cheaper to fly with a layover from Chicago O'Hare Intl Airport to the Dominican Republic?

    Yes. Nonstop flights from Chicago O'Hare Intl Airport to the Dominican Republic average $557 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Boston Logan Intl (BOS) from $380
    • Punta Cana (PUJ) from $444
    • Fort Lauderdale (FLL) from $483

  • How long is a flight from Chicago O'Hare Intl Airport to the Dominican Republic?

    Flights from Chicago O'Hare Intl Airport to the Dominican Republic take 4h 41m on average.

  • How often are flights from Chicago O'Hare Intl Airport to the Dominican Republic delayed and what's the average delay?

    19% of flights on this route are delayed by at least 15 minutes. The average delay is 2h 37m.

  • Which cabin classes are available on flights from Chicago O'Hare Intl Airport to the Dominican Republic?

    On flights from Chicago O'Hare Intl Airport to the Dominican Republic you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks in the Dominican Republic?

    KAYAK travelers' favorite landmarks in the Dominican Republic include:

    • Playa Dorada
    • Catedral Primada de América
    • Playa Juanillo
    • Centro Olimpico Juan Pablo Duarte

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to the Dominican Republic?

    The earliest nonstop flight from Chicago O'Hare Intl Airport to the Dominican Republic departs at 4:20 am and the latest departs at 12:12 pm. Nonstop flights take about 4h 41m.

Your guide to booking Chicago O'Hare Intl Airport to the Dominican Republic flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 3 weeks before your trip. KAYAK data shows fares in this window are around 16% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for February when flights are typically cheapest and avoid June when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Thursday cost about 20% more on average, so being flexible with your travel dates could help you save.
  • If arriving on time matters more than price, consider flying with one of the most punctual airlines on this route: American Airlines, United Airlines and Frontier.
  • If you're looking to save, Santo Domingo Las Americas (SDQ) is the cheapest airport to fly into from Chicago O'Hare Intl Airport. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Punta Cana, which is the most popular destination in the Dominican Republic. From there, it's easy to continue on to other popular destinations such as Puerto Plata, Santo Domingo and La Romana.
  • If you want the shortest trip, choose the Chicago O'Hare Intl Airport to the Dominican Republic nonstop route. If you'd rather save money, the route via Boston Logan Intl (BOS) is usually the cheapest.

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 10319 reviews
6.7Food
7.1Entertainment
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

10.0 ExcellentMonyee, Sep 2026
Read more United Airlines reviews

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

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.

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Non-stop commercials were frustrating when trying to view direct TV

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

Great. I was in mint class. Security was spectacular. A lot of room on the flight! And the WiFi worked this time- it didn’t work the last time and I am on a business trip so that was a problem.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

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.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

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.

More options for your flight from O'Hare Intl to the Dominican Republic

Complete your trip to the Dominican Republic with a hotel stay or car rental