$126 Find Cheap Flights from Chicago O'Hare Airport to Dominican Republic - Compare and Save

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 8/29. 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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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$412
Santo Domingo
Santo Domingo1 stop$381
Puerto Plata
Puerto Plata1 stop$558
Punta Cana
Punta Cananonstop$412
Santo Domingo
Santo Domingo1 stop$381
Puerto Plata
Puerto Plata1 stop$558

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, Sep 21 - Thu, Sep 24
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
JetBlue Logo
3:49 pm - 11:31 pm
STI
-
ORD
8h 42m
1 stop
$370JetBlue
Mon, Sep 21 - Thu, Sep 24
JetBlue Logo
6:00 am - 1:27 pm
ORD
-
STI
6h 27m
1 stop
JetBlue Logo
3:49 pm - 11:31 pm
STI
-
ORD
8h 42m
1 stop
$378JetBlue
Mon, Sep 21 - Thu, Sep 24
American Airlines Logo
8:55 pm - 2:15 pm
ORD
-
STI
16h 20m
2 stops
American Airlines Logo
3:15 pm - 7:58 am
STI
-
ORD
17h 43m
2 stops
$383American Airlines
Thu, Oct 1 - Sun, Oct 4
American Airlines Logo
2:30 pm - 2:15 pm
ORD
-
STI
22h 45m
1 stop
American Airlines Logo
3:15 pm - 11:32 pm
STI
-
ORD
9h 17m
1 stop
$392American Airlines
Wed, Oct 21 - Thu, Nov 19
Delta Logo
5:30 am - 1:41 pm
ORD
-
SDQ
7h 11m
1 stop
Delta Logo
6:45 am - 7:15 pm
SDQ
-
ORD
14h 30m
1 stop
$408Delta
Sat, Aug 15 - Sat, Aug 22
Arajet Logo
12:12 pm - 5:57 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
7:02 am - 11:12 am
PUJ
-
ORD
5h 10mnonstop
$412Arajet
Sat, Nov 14 - Sat, Nov 21
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$413Arajet
Tue, Oct 20 - Tue, Nov 17
Delta Logo
7:00 am - 6:24 pm
ORD
-
SDQ
10h 24m
1 stop
Delta Logo
6:45 am - 6:40 pm
SDQ
-
ORD
13h 55m
2 stops
$413Delta
Tue, Nov 24 - Wed, Dec 2
Air Canada Logo
7:05 am - 2:45 pm
ORD
-
POP
29h 40m
1 stop
Air Canada Logo
3:40 pm - 2:52 pm
POP
-
ORD
25h 12m
1 stop
$558Air Canada
Tue, Nov 24 - Wed, Dec 2
Air Canada Logo
10:57 am - 2:45 pm
ORD
-
POP
25h 48m
2 stops
Air Canada Logo
3:40 pm - 7:58 am
POP
-
ORD
18h 18m
2 stops
$576Air Canada
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 5 days was to Punta Cana, at $340 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 $340.

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 $423 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 $563.

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 $602, 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 $84 (return) on average. On the other hand, the most expensive months are February and November, when the average cost of round-trip tickets is $1,223 and $1,176 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 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 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 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 seasonSeptember
Cheapest flight$126
Best time to beat the crowds with an average 10% 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.

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 9927 reviews
8.1Crew
7.7Boarding
6.7Food
7.3Comfort
7.1Entertainment
Airline reviews

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

6.0 GoodMatthew, Jul 2026
ORD - SEA
Read more United Airlines reviews

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

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

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.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

The ticket you issued was an hour after when the real flight was

I didn’t get a chance to experience anything because the 3rd party company that receives payment did a really bad job. After I received confirmation number I went to bed then I tried to check in my confirmation number did not work then I received a massage that my payment did not go through I called the company to rectify the problem and I was told that confirmation the whole thing was cancelled and that they couldn’t do anything about it and hang up the phone. So I decided to purchase a new ticket from another airline. I will never use kayak again and I’ll make sure all the people in my circle doesn’t deal with you guys.

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

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