$125 Find Cheap Flights from Chicago O'Hare Airport to Dominican Republic

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to the Dominican Republic departing on 5/9. 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.
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1 adult, Economy, 0 bags

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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 72 hours
Punta Cana
Punta Cananonstop$291
Santo Domingo
Santo Domingo1 stop$301
Puerto Plata
Puerto Plata1 stop$449
Punta Cana
Punta Cananonstop$291
Santo Domingo
Santo Domingo1 stop$301
Puerto Plata
Puerto Plata1 stop$449

Book Cheap O'Hare Intl to the Dominican Republic Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to the Dominican Republic 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 O'Hare Intl to the Dominican Republic

Mon, Apr 13 - Sat, Apr 18
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$291Arajet
Mon, Apr 20 - Sat, Apr 25
Arajet Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$292Arajet
Fri, Apr 17 - Sat, Apr 18
Arajet Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$293Arajet
Wed, Mar 25 - Thu, Mar 26
Spirit Airlines Logo
7:17 am - 2:35 pm
ORD
-
STI
6h 18m
1 stop
Spirit Airlines Logo
3:43 pm - 11:17 pm
STI
-
ORD
8h 34m
1 stop
$334Spirit Airlines
Sun, Mar 22 - Mon, Mar 23
Spirit Airlines Logo
7:17 am - 2:35 pm
ORD
-
STI
6h 18m
1 stop
Spirit Airlines Logo
2:46 am - 11:17 am
STI
-
ORD
9h 31m
1 stop
$354Spirit Airlines
Mon, Apr 6 - Fri, Apr 10
Copa Airlines Logo
3:05 pm - 11:24 am
ORD
-
POP
19h 19m
1 stop
Copa Airlines Logo
12:34 pm - 1:13 am
POP
-
ORD
13h 39m
1 stop
$449Copa Airlines
Mon, May 4 - Fri, May 8
JetBlue Logo
6:00 am - 2:03 pm
ORD
-
POP
31h 03m
2 stops
JetBlue Logo
1:52 pm - 9:36 pm
POP
-
ORD
32h 44m
2 stops
$580JetBlue
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
8:46 pm - 2:30 pm
ORD
-
POP
16h 44m
2 stops
American Airlines Logo
3:30 pm - 7:24 am
POP
-
ORD
16h 54m
2 stops
$594American Airlines
Mon, May 4 - Sat, May 9
JetBlue Logo
6:00 am - 2:03 pm
ORD
-
POP
31h 03m
2 stops
JetBlue Logo
3:12 pm - 7:41 am
POP
-
ORD
17h 29m
1 stop
$596JetBlue
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
6:50 am - 2:30 pm
ORD
-
POP
6h 40m
1 stop
American Airlines Logo
3:30 pm - 1:25 pm
POP
-
ORD
22h 55m
1 stop
$599American Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Dominican Republic from Chicago O'Hare Intl Airport found in the last 72 hours was to Punta Cana, at $261 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 72 hours was $261.

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport to the Dominican Republic depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Dominican Republic is generally at night, when round-trip flights cost $375 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 $518.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $578, 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?

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 the Dominican Republic, 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 the Dominican Republic is January, when tickets cost $426 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $584 and $555 respectively.

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

The average price of all round-trip flights from Chicago O'Hare Intl Airport to the Dominican Republic clicked on KAYAK for each day over the last 12 months.

For Chicago O'Hare Airport to Dominican Republic, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Dominican Republic back to Chicago O'Hare Airport, the best deals are generally found on Friday, 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 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 the Dominican Republic, 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 the Dominican Republic, you should book around 2 weeks before departure, which saves you about 44% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$125
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 11% 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.

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 9413 reviews
7.7Boarding
6.6Food
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

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

My flight was delayed by over an hour and the turbulance was horrible.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

I had a great experience from booking to boarding to landing. This was the best experience from all the flights I’ve had with Spirit so far! The price and times were affordable and perfect. I will fly with them again soon!

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

Horrible we lost a day at the destination. Flight was canceled at 2am left us scrambling for another airline to get us to destination

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

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 !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

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

Information on your arrival and departure airports