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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 5 days
Booking Insights

Price, demand and travel trends for Chicago 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 to the Dominican Republic cheaper or more expensive than last year?

Fares from Chicago to the Dominican Republic are running about the same as they were around this time last year, averaging $549 round-trip.

What are the cheapest fares from Chicago to the Dominican Republic right now?

Here are the cheapest round-trip fares from Chicago to the Dominican Republic on KAYAK in the last week:

• Santo Domingo Las Americas (SDQ) from $362
• Punta Cana (PUJ) from $364
• La Romana (LRM) from $380
• Puerto Plata La Union (POP) from $526
• Santiago de los Caballeros (STI) from $736

What’s the cheapest month to fly from Chicago to the Dominican Republic?

February is the cheapest time of year to fly, with average fares of $439. Prices are highest in June, when average flight costs increase to around $665.

When is the best time to book flights from Chicago 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?

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 $532
• Punta Cana (PUJ) from $557
• Santiago de los Caballeros (STI) from $598

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

Monday tends to be the cheapest day to fly from Chicago to the Dominican Republic, while Sunday is the most expensive. Fares run about 18% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago 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 $584.

Key details for Chicago to the Dominican Republic flights

Low season

September

Cheapest flight

$162
Beat the crowds with an average 43% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Santo Domingo

Your Chicago 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 to the Dominican Republic?

    Yes. Fares from Chicago to the Dominican Republic are low right now. As a rule of thumb, a round-trip under $414 (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 to the Dominican Republic?

    Over the past 12 months, round-trip fares from Chicago to the Dominican Republic have ranged from $414 to $743.

  • What are the main airports serving the Dominican Republic?

    The Dominican Republic has 7 airports. The three busiest are Punta Cana (PUJ) (83% of arrivals), Santo Domingo Las Americas (SDQ) (11%) and Santiago de los Caballeros (STI) (3%).

  • What airlines fly nonstop from Chicago to the Dominican Republic?

    Based on the flight schedule for the next 3 months, 4 airlines offer nonstop flights on this route:

    • American Airlines
    • United Airlines
    • Arajet
    • Southwest

  • Where in the Dominican Republic can I fly nonstop from Chicago?

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

  • Is it cheaper to fly with a layover from Chicago to the Dominican Republic?

    Yes. Nonstop flights from Chicago to the Dominican Republic average $559 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 to the Dominican Republic?

    Flights from Chicago to the Dominican Republic take 4h 41m on average.

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

    21% of flights on this route are delayed by at least 15 minutes. The average delay is 2h 20m.

  • Which cabin classes are available on flights from Chicago to the Dominican Republic?

    On flights from Chicago to the Dominican Republic you can book 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 to the Dominican Republic?

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

  • 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.

Your guide to booking Chicago 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 Sunday cost about 18% 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, Frontier and Southwest.
  • If you're looking to save, Santo Domingo Las Americas (SDQ) is the cheapest airport to fly into from Chicago. 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 nonstop route from Chicago Midway Airport to the Dominican Republic. If you'd rather save money, the route from Chicago O'Hare Intl Airport via Boston Logan Intl (BOS) is usually the cheapest.
  • 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
SouthwestOverall score based on 4214 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

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.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

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.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Perfect. On time and the weather was perfect so we came in a few minutes early.

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

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

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

Delayed fly, employees at the counter not professional and lack empathy to help, crew inside the plane very rude and unfriendly my fly was delayed for 2 hours. For being this the first time I will say if there is not other option then I will fly with this airline. One more thing, the pilot never said a wakes the whole fly but until we are about to descend. Not a welcome message the wether at the destination and time to arrival. It seems that the airplane was flying by itself without pilots. Terrible.

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

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 Chicago to the Dominican Republic

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