$114 Find Cheap Flights from Chicago to the 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 Chicago to the Dominican Republic departing on 1/21. 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 Chicago to the Dominican Republic

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Book Cheap Chicago 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 Chicago 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 Chicago to the Dominican Republic

Tue, Mar 10 - Sun, Mar 15
Multiple Airlines Logo
7:20 am - 1:03 pm
ORD
-
PUJ
4h 43mnonstop
Multiple Airlines Logo
6:00 pm - 10:10 pm
PUJ
-
ORD
5h 10mnonstop
$252Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
Arajet Logo
10:27 am - 5:12 pm
ORD
-
PUJ
4h 45mnonstop
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
$253Arajet
Sat, Jan 17 - Sat, Jan 24
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m1 stop
Spirit Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
$258Spirit Airlines
Sat, Feb 21 - Fri, Feb 27
Spirit Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m1 stop
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m1 stop
$259Spirit Airlines
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
6:10 am - 3:07 pm
MDW
-
PUJ
6h 57m1 stop
Frontier Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$327Frontier
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
6:10 am - 3:07 pm
MDW
-
PUJ
6h 57m1 stop
Frontier Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$328Frontier
Sat, Jan 24 - Sat, Feb 7
Delta Logo
7:05 am - 3:53 pm
ORD
-
POP
6h 48m1 stop
Delta Logo
5:08 pm - 11:56 pm
POP
-
ORD
8h 48m1 stop
$388Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:45 am - 3:40 pm
ORD
-
POP
6h 55m1 stop
Delta Logo
3:55 pm - 8:30 am
POP
-
ORD
17h 35m1 stop
$389Delta
Sat, Jan 24 - Sat, Feb 7
American Airlines Logo
8:50 pm - 2:32 pm
ORD
-
POP
15h 42m2 stops
American Airlines Logo
4:42 pm - 7:22 am
POP
-
ORD
16h 40m2 stops
$392American Airlines
Mon, Feb 16 - Sat, Feb 21
American Airlines Logo
5:00 am - 3:35 pm
ORD
-
POP
8h 35m2 stops
American Airlines Logo
2:22 pm - 11:58 pm
POP
-
ORD
11h 36m2 stops
$417American Airlines
Booking Insights

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?

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

The cheapest ticket to the Dominican Republic from Chicago found in the last 72 hours was to Punta Cana, at $243 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 $243.

Can I save money by flying with a layover from Chicago 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 $531, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago 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 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 to the Dominican Republic is August, when tickets cost $459 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $631 and $616 respectively.

What’s the cheapest day of the week to fly from Chicago to Dominican Republic?

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

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 Friday and avoiding Mondays for the best deals.

How far in advance should I book a flight from Chicago 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 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 to the Dominican Republic, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$114
Best time to beat the crowds with an average 31% 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

  • Does the Midway Chicago International Airport have pet relief areas?

    The Midway Chicago Airport has an outdoor facility fenced in area with benches and bags provided for pet owners. There is also an indoor facility with pet parent sitting area. The facilities are wheelchair accessible and pet owners are provided with bags for disposing off pet waste.

  • What are the kid’s friendly features offered by the Midway Chicago Airport?

    The airport offers safe and convenient travel for kids. It also offers child friendly restaurants which are easy to find through the midway. The restaurants provide high chairs and kid’s menus.

  • Does the Midway Chicago Airport offer facilities for business travelers?

    The airport has power stations available for the business travelers. There are also a number of amenities which can help in relaxing and traveling comfortably. It also offers rooms for business meetings and conventions just an easy drive from the midway.

  • What are the car rental services at Santo Domingo Airport (SDQ)?

    If you are a driver with 25 years and above you can enjoy car rental services such as zero credit card fees and flexibility on most bookings with free cancellation. Some of the companies that offer rental services at this airport include Alamo, Economy AVIS, Budget, National and Sixt. Head to the airport’s North terminal at the centralized exit to the location of the car rental desks.

  • How does KAYAK find such low prices on flights from Chicago to the 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 to the Dominican Republic.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the 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 to the 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 to the 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 to the 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 to the Dominican Republic up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • 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 $385 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 $519.

Top tips for finding cheap flights to the Dominican Republic

  • If you are traveling to the Dominican Republic from Chicago Midway International Airport (MDW) there are several ways you can use to get to the airport. You can either use public transportation by taking a train from the orange line station to the airport. You can also take the airport shuttles and regional buses that service the midway to the airport. There are also a number of taxis and ride share companies that can also take you to the airport. If you have a personal car you can also conveniently access the airport.
  • If you are a private car owner, there are several parking options available at the Chicago Midway International Airport. Such options include daily, hourly and long term economy parking. Parking facilities include friendly customer care service, secured indoor parking garages and 24/7 video CCTV camera surveillance.
  • If you need to relax and travel comfortably there are spacious rooms and lounges at the Midway Chicago Airport. They offer services and amenities such as beverages, freshly made food and also yoga room where one can meditate .There are also various hotels that offer accommodations for passengers that require an extended stay or rest between flights at the airport.
  • Wheelchair and disability features are available at The Midway Chicago International Airport. They offer features such as the accessibility guide which will point you in all the directions and help you with your navigation through the airport. If you need assistance through the midway the airline offers wheelchair assistance to passengers with mobility impairment. All the elevators have braille and raised numerals for the passengers with eye defections.
  • If you are a nursing mother The Midway Chicago International Airport offers a number of facilities. Such facilities include MAMAVA pods that offer a tranquil space for the breastfeeding mothers who would like to do so in a private setting. The Midway Chicago Airport also offers mother’s rooms with comfortable seating and baby changing stations .The rooms also offer electric breast pumps.

Reviews of the top 5 airlines serving from Chicago to the Dominican Republic

 
Need help choosing which airline to fly with from Chicago 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.
7.9
DeltaOverall score based on 8023 reviews
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

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. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

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

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Everything you need to know for your flight from Chicago to the Dominican Republic

Cabin class types available on flights to the Dominican Republic

Cabin classes available on flights to the Dominican Republic. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.