
Cheap Flights from Chicago to the Dominican Republic
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Chicago to the Dominican Republic Plane Tickets
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KAYAK's insights & trends for Chicago to the Dominican Republic flights
Get data-powered insights and trends into flights from Chicago to the Dominican Republic to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest Chicago to the Dominican Republic flight route?
The cheapest ticket to the Dominican Republic from Chicago found in the last 5 days was to Punta Cana, at $239 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 $239.
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 $459 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 $587.
Can I save money by flying with a layover from Chicago to the Dominican Republic?
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $652 on average.
What is the cheapest month to fly from Chicago to the Dominican Republic?
The cheapest month for flights from Chicago to the Dominican Republic is January, when tickets cost $441 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $683 and $623 respectively.
What’s the cheapest day of the week to fly from Chicago to Dominican Republic?
If your flying dates are flexible, you should consider flying to Dominican Republic on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Chicago to Dominican Republic. For your return ticket, we recommend flying on a Sunday and avoiding Fridays for the best deals.
How far in advance should I book a flight from Chicago to the Dominican Republic?
To get a below average price on the flight from Chicago 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.
Which airlines fly non-stop between Chicago and Dominican Republic?
There are 8 airlines that fly nonstop from Chicago to the Dominican Republic. They are: American Airlines, Frontier, JetBlue, Southwest, Hahn Air, Arajet, WorldTicket and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $217 for a round-trip flight to Punta Cana (PUJ). On average, Arajet offers the best prices for nonstop flights between Chicago and Dominican Republic.
Which airlines provide the cheapest flights from Chicago to the Dominican Republic?
In the past 5 days, the cheapest round-trip tickets from Chicago to the Dominican Republic were found on JetBlue ($357) and American Airlines ($360).
How long does a flight from Chicago to the Dominican Republic take?
The duration of a flight to the Dominican Republic depends on your arrival airport. The shortest routes to the Dominican Republic from Chicago are to Punta Cana, which takes 4h 27m, Santo Domingo, which takes 6h 25m, and Puerto Plata, which takes 6h 35m.
Which cabin class options are there for flights between Chicago and Dominican Republic?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago to the Dominican Republic?
The earliest flight from Chicago to the Dominican Republic departs at 4:20 am, landing in Punta Cana at 11:05 am.
What’s the latest departure time from Chicago to the Dominican Republic?
If you prefer to fly at night, the latest flight from Chicago to the Dominican Republic jets off at 12:12 pm and lands in Punta Cana at 5:57 pm.
Good to know
Low season | September |
|---|---|
High season | March |
Cheapest flight | $143 |
FAQs - booking Dominican Republic flights
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Reviews of the top 5 airlines serving from Chicago to the Dominican Republic
Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.
Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.
Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.
A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack
I like the staff members they were super nice and helpful very sweet people :)
Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.
Overall good, just screaming kids in the area the whole flight.
OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.
The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.
I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.
Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.
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.
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.
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.
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
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.